Vacation Rentals By Owner In Orleans, MA

Paradise On Cape CodbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis home sits right next to a wetland preserve, making wildlife viewing a spectacular sight from the balcony! Skakket Beach, known for its breathtaking sunsets, is just under two miles away, while an oceanside beach, Nauset Beach, is only three miles away in the other direction. Plus, downtown Orleans is a short drive away if you want to spend a day meandering along Main Street looking through shops and trying some local cuisine. Be sure to take the scenic drive to Provincetown and check out the Race Point Lighthouse!brbrIf a getaway to Cape Cod is on the horizon, this inviting home is just the place to indulge in a bit of rest and relaxation while still being in the heart of everything this area has to offer! Newly renovated, this retreat is perched on a hill overlooking one and a half acres of trees and foliage, providing natural privacy from neighbors. The spacious second-story deck offers a wonderful place to have a cookout in warmer weather and cap long days of adventure. If you feel like having some downtime indoors, the chef of the group can whip up a warm meal in the full kitchen as the other guests read in the cozy living area or break out a few board games for a night of friendly competition!brbrTHINGS TO KNOWbrThe hot tub is not for guest use.brbrParking notes: There is free parking available for 2 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Stylish Orleans home with spacious deck - near bay & ocean beach

Orleans, Massachusetts, United States

Bed

3

Bath

8

Sleeps

$754.33

Summary:brbrSpacious, amenity-rich home with sweeping Atlantic views, a heated pool, and perfect indoor-outdoor flow for unforgettable Cape Cod summers.brbrbrbrThe Space:brbrWelcome to this stunning Cape Cod retreat perched in a quiet Orleans neighborhood with panoramic views of the Atlantic Ocean. This spacious 5-bedroom, 2-bathroom home comfortably accommodates up to 12 guests and offers a private, elevated vacation experience just minutes from Nauset Beach.brbrbrbrThe heart of the home is the open kitchen, dining area, and great room, where large windows frame ocean views and natural light pours in. The kitchen features two dining tables—one seating 8 and the other 4—along with all the essentials for entertaining, including a, lobster pot, blender, and drip coffee maker. Relax in the great room on oversized sofas and club chairs, or enjoy casual conversation around the additional round table with seating for four.brbrbrbrStep outside to a 40’ x 26’ ocean-facing deck, perfect for grilling and gathering. With an outdoor sectional under a large cantilever umbrella and a dining table for 8, you’ll find yourself spending entire afternoons here. Adjacent to the deck is a charming screened-in room with even more seating and dining space, ideal for morning coffee or evening drinks.brbrbrbrCool off in the heated in-ground pool while taking in more spectacular views. Additional amenities include a fully stocked kitchen, WiFi, smart TV with streaming, gas grill, outdoor shower, and beach gear (chairs, wagon, cooler, boogie boards, floaties).brbrbrbrLocated just 2–2.5 miles from Nauset Beach and close to favorites like The Knack and La Bella Vita, this home is the perfect launchpad for your Cape Cod adventure.brbrbrbrLayout of Bedrooms & Bathrooms: brbrbrbrMain LevelbrbrBedroom #1 - King BedbrbrBedroom #2 - Queen BedbrbrbrbrBathroom #1 - Full Bathroom with Bathtub/ShowerbrbrbrbrLower Level brbrBedroom #3 - Queen BedbrbrBedroom #4 - 2 Twin BedsbrbrBedroom #5 - Double Bed, 2 Twin Beds, Twin Trundle BedbrbrBathroom #2 - Full Bathroom with Showerbrbrbrbrbrbr**Linens and bath towels are included.**brbr**This is NOT a pet-friendly home**brbrbrbrOther Things to Note:brbr-

Oceanview Retreat with Pool and Expansive Outdoor Living

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Select Dates for Price

California Contemporary, Walk to Beach, 1.3 Wooded Acres

Orleans, Massachusetts, United States

The house is equipped with Medical Grade H13 HEPA Air Purification Filters throughout!brbrPrestigious location within the Quanset Harbor Club Association, 3 houses away from the community’s private beach on beautiful Pleasant Bay. At the beach, you’ll find our three kayaks (two singles and a tandem) and sailing dinghy, available for your use. The house, located on 1.3 beautifully landscaped, wooded and secluded acres, is newly furnished with a new gourmet kitchen. The property includes a fire pit, gazebo and storage shed. The shed houses 9 bicycles, complete with helmets, which are waiting for you to use them. Come home to an outdoor shower before you relax on the patio or in the house.brbrBeamed ceilings in the living room, kitchen and all bedrooms. The centerpieces in the living room are a stone and brick floor to ceiling fireplace and a 63 inch TV for your viewing pleasure. An additional floor to ceiling brick fireplace is found in the gourmet kitchen. Sliding glass doors from the living room, hallway and two bedrooms to the beautiful patio, complete with a glass table that seats 8 people. The patio has complete privacy with woods surrounding the house.brbrThis house is great for families and for couples. Over 2,400 square feet of living space, all on a single floor. Wide plank hardwood floors. Two bedrooms feature king size beds and are on opposite ends of the house, separated by the Living Room and Kitchen. Each of them has a nearby room that can be used for your children, one features two full size beds while the other features two twin size beds with an adjoining greenhouse room. Sleep 8 to 10 people. There are two full bathrooms, one on each side of the house. One has a tub and shower with double sinks, the other has a shower with a single sink, plus the outdoor shower. Separate laundry room with generous storage and a utility sink.brbrFURTHER DETAILSbrbr• Central air conditioningbr• Premium cable -- three TVs (63 inch and 2 40 inch)br• Landline telephone servicebr• Wireless high speed internet accessbr• A fully equipped kitchen, a chef s delightbr• Bosch Dishwasherbr• Jennair modular downdraft cooktop with indoor grillbr• Monogram Advantium Oven for speedcook, convection, microwave and warmingbr• Wet bar with wine refrigeratorbr• Kitchen Aid Refrigeratorbr• Bosch Washer and Bosch Dryerbr• Outdoor showerbr• Toaster Ovenbr• Wine Glasses, Gourmet Pots and Pans, Chef’s knivesbr• Outdoor grillbr• Outdoor fire pitbr• 3 kayaks (2 singles and a tandem)br• Sailing Dinghybr• 9 bicycles, plus a tandem, with helmetsbrbrAdditional pictures may be seen at: The SLIDESHOW button on the top right gives a great show.

Bed

Bath

10

Sleeps

$659.96

Nauset Beach GetawaybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNauset Dream – Two-Unit Family RetreatbrbrThis two-unit Cape Cod property includes both the upper-level home and a private lower-level apartment, making it ideal for extended families or groups who want to stay together while enjoying separate living spaces. Each unit has its own entrance, living area, eat-in kitchen, and washer/dryer for convenience and privacy. The units are not connected internally; guests move between them via a short, easy outdoor path.brbrJust steps from Nauset Beach, you can skip parking and fees, enjoy morning swims, take midday breaks, or head out for spontaneous beach strolls. Early mornings are especially peaceful, perfect for a quiet visit to the shore before the crowds arrive.brbrThe interiors feature classic Cape Cod charm with original wooden cabinetry and traditional layouts. Both living areas include Apple TV for streaming with your own accounts. A rinse area with a showerhead is available for washing off sand (not a fully private shower). Standard bath linens, extra beach towels, chairs, and games are provided, and guests can enjoy the shared patio with a gas grill for casual outdoor meals.brbrBuilt by hand by our father and grandfather, this family home has been cared for over generations. We grew up here and now share it with our own children, hoping you feel the same Cape Cod magic.brbrConveniently located for exploring Orleans and the surrounding Cape—ice cream shops, dining, grocery stores, kayak and bike rentals, and the Cape Cod Rail Trail are all within 10–15 minutes. The property is also well positioned to visit Wellfleet, Hyannis, Skaket Beach, Crystal Lake, and other local favorites.brbrPerfect for families and multi-generational groups, this retreat balances privacy, comfort, and an unbeatable location.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 5 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Charming home steps to beach, includes 2 full units with patio, grill, & views

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$506.57

Barley BreezebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to this beautiful and private Cape Cod retreat in Orleans, MA, where tranquility meets adventure just steps from Pochet Bay. This charming two-story house is the perfect spot for a family vacation, offering easy access to some of the best beaches in the area. Nature lovers will appreciate the scenic waterfront paths nearby, ideal for bird watching and enjoying the stunning coastal views.brbrInside, the home boasts a delightful blend of hardwood floors and nautical decor, creating a warm and inviting atmosphere. Each room is equipped with air conditioning to ensure your comfort during your stay. The newly remodeled kitchen, completed in 2025, is a culinary delight, featuring a lobster pot for preparing fresh seafood. Gather around the dining table indoors or step outside to the furnished deck for an al fresco dining experience under the stars.brbrFor entertainment, the living area features a wall-mounted flat-screen TV, while a cozy den and a basement with a pool table provide additional options for relaxation and fun. Outdoor enthusiasts will love launching kayaks or canoes just down the road into Pochet Bay, where you can explore the sandy shores of Pochet Island and hike scenic trails.brbrDowntown Orleans is just a short drive away, offering a variety of restaurants, shops, and art galleries to explore. Don't miss the chance to charter fish at Rock Harbor, watch the sunset at Skaket Beach, or bike through Nickerson State Park and the Cape Cod Rail Trail. With a range of amenities including a washer/dryer, internet, and a gas grill, this Cape Cod retreat has everything you need for a memorable vacation. Book your stay today and experience the best of Cape Cod!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brFree high-speed WiFibrOutdoor shower availablebrIncludes beach towels and chairs.brPlease note there's no central A/C, but A/C units are installed in every bedroom.brAccess and special features for guests with limited mobility including a first-floor suite.brbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Two-story home w/new kitchen, washer/dryer, large yard, & pool table

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$498.54

Arey's Pond PointbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrKayakers and nature lovers take note! This four-bedroom, two-bathroom house sits on 2+ waterfront acres in Orleans, offering extraordinary privacy with exquisite water views of historic Arey's Pond, part of Pleasant Bay. (Please note, this is a saltwater pond.) The adjoining 11+ acres of conservation land let you leave the crowds behind.brbrNauset and Skaket Beaches and a local bike trail are all around four miles away via local roads. Even better, two freshwater swimming lakes are within a mile on quiet lanes. This is a great backroad area for walking, biking, and enjoying nature, yet it's convenient to downtown Orleans and Chatham with their great shops and restaurants.brbrThere's also convenient access to Arey's Pond, which connects to Pleasant Bay (prime water for sailing), if you provide your own watercraft.brbrThe house offers the easy, indoor-outdoor flow of a classic summer home. When you're having a relaxing dinner on the porch after a day at the beach, you'll know what makes Cape Cod so special. The entrance opens up into a hallway, with a tiled kitchen on your left offering all the appliances, cookware, and utensils you need. After preparing a memorable feast, enjoy it in the dining area while indulging in the view of the pond and lively conversation together. The screened porch adjacent to the living room and dining area serves as an excellent alternative. Few things compare to great food while appreciating the westerly breezes and watching the sun go down. The bathrooms were updated in recent years yet remain in perfect keeping with the classic style of the house. This first-floor bathroom includes a vanity and walk-in shower.brbrThe first floor hosts two bedrooms, with one featuring a king and the other with two twin beds. The second floor boasts an additional two bedrooms, with one also featuring a king and the other two twins. The twin bedroom even has a writing desk, in case inspiration strikes while observing the pond. The bathroom in the hallway has a tub and a shower, as well as a single-sink vanity.brbrThe living room and dining areas have premium views of the pond and sunsets. Take advantage of the sofa and armchairs to relax while viewing your favorite shows on the 42-inch TV before turning in for a blissful night's rest.brbrTHINGS TO KNOWbrPlease note this home requires a seven-night minimum stay from late June through early September.brThere is a mini-split downstairs and a window AC unit upstairs.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

West-facing pure waterfront home in Orleans, overlooking Arey's Pond

Orleans, Massachusetts, United States

Bed

Bath

8

Sleeps

$1429.48

This property is professionally managed by Pretty Picky Propertiesbr brLuxurious 5- Bedroom Retreat with Heated Pool & Hot Tub – Walk to Water!brbr5 bedrooms sleeps 12brLinens included, beds madebrRents Friday to Friday in Peak SeasonbrPets Considered (Small dog)brbrPlease note: pool and hot tub are open Memorial Day - Columbus Day.brbrEscape to the heart of Lower Cape Cod in this newly renovated, luxury vacation home in East Orleans! Perfect for families and groups, this spacious 5-bedroom retreat offers the perfect blend of modern comfort and classic coastal charm.brbrInside, you'll find a fully equipped, modern kitchen with everything you need to prepare gourmet meals, plus a large dining room with seating for 10 -- perfect for gathering after a day at the beach. The main level features two elegant bedrooms, both with a queens, each with new, spa-like private baths. Upstairs, two additional bedrooms. One has a spacious King and the other with a queen plus a twin with a trundle. There is a luxurious full bath upstairs as well. New for 2026: 5th bedroom as primary bedroom and private en-suite.brbrStep outside and experience your private Cape Cod oasis -- a heated saltwater pool, relaxing hot tub, gas fire pit and a fully equipped outdoor kitchen make entertaining a breeze. Lounge in the poolside cabana, fire up the grill, or unwind under the stars after a day of exploring.brbrNature lovers will love the short walk to a nearby saltwater river, perfect for kayaking and paddleboarding. Plus, you're just under a mile to Orleans Center for shopping and dining, and a 5-minute drive to both Nauset Beach and Skaket Beach—giving you the best of both the Atlantic Ocean and Cape Cod Bay.brbrThis stunning getaway has everything you need for an unforgettable Cape Cod vacation.brbrPlease enter in your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.brbrBe sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod.brbrIt's your vacation, Get Picky! ®

Orleans Dreams: 013-OP Luxurious 5-Bedroom Retreat with Heated Pool & Hot Tub – Walk to Water!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$364.27

Namskaket RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled in the charming town of Orleans, MA, this delightful three-bedroom house offers the perfect blend of quiet privacy and convenient access to the stunning bayside shores. Just a short stroll from the pristine sands of Skaket Beach, this home is ideal for families seeking sun-soaked days filled with swimming and exploring tidal pools. Perched on a spacious corner lot, the property features a brand-new kitchen and a thoughtful layout, with a master suite on one side and two guest bedrooms on the other, ensuring comfort and convenience for all.brbrInside, the welcoming living area invites relaxation with its comfy seating arrangement, including a sofa, love seat, and armchair. Enjoy movie nights on the 50” smart TV, equipped with cable and a DVD player, or curl up in the sunny reading nook with a good book. The well-equipped kitchen boasts brand-new stainless steel appliances, perfect for whipping up delicious meals. Gather around the dining table for six or perch at the counter for two while dinner simmers.brbrStep outside onto the large deck that overlooks the backyard, an ideal spot for morning coffee or evening barbecues on the gas grill. With the provided beach gear, including chairs, toys, and an umbrella, you can easily pack up for a day at the beach. Additional family-friendly amenities, such as a Wii, video games, and children's books, ensure that everyone has something to enjoy.brbrLocated just a mile from the town center, you can explore local attractions like the Hog Island Beer Company for great food and live music. Nauset Beach is also a quick drive away, offering more opportunities for sun and surf. Whether you're looking to relax or embark on outdoor adventures, this Orleans retreat is the perfect home base for your Cape Cod getaway.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 3 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Skaket Beach escape: Corner-lot home with big yard - walk to Warm Bayside Shore

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$603.72

The Salty OnebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrAround the corner from the Cape Cod Rail Trail and near Skaket Beach, this beautifully renovated 4BR/2BA classic home is the perfect bayside retreat. Find your bliss in the manicured yard, complete with a cookout-ready stone patio.brbrCoastal colors and fine furnishings adorn the spacious interior. The charming dining room invites memorable family meals beside a gas fireplace.brbrLIVING AREASbrbrThe light-filled living room features a soothing color palette. Recline on a plush sofa and two armchairs and find your favorite shows on the 50” TV. A selection of DVDs, books, and games expand your entertainment options.brbrKITCHEN & DININGbrbrPrepare your favorite foods in the modern kitchen, outfitted with a full suite of appliances, and fully stocked with all the gadgets you might need. Ample counter space makes it easy to prepare ingredients, and the breakfast nook seats six.brbrThe window-lined dining room has a table for eight and a gas fireplace. Share special meals by the light of a chandelier.brbrBEDROOMS & BATHSbrbrThis home sleeps up to eight guests in between the four bedrooms and a bonus area. The bedrooms are located on the second floor.brbrMake yourself at home in the tranquil master bedroom, detailed with a queen-size bed and a flat-screen TV. The second and third bedrooms feature comfy queen-size beds, while the fourth guest room has a full-size bed. Two twin-size beds await in the bonus area.brbrThe guest bathroom on the second floor is appointed with a double vanity and a tub/shower combination. A sparkling walk-in shower rounds out the bathroom on the main floor.brbrOUTDOOR AREASbrbrThe oversized yard is the perfect for lawn games or simply relaxing in the shade. Make use of the gas grill and dine alfresco at the table for four.brbrAn outdoor shower is handy after fun-filled days at the beach.brbrEXTRA AMENITIES & MORE DETAILSbrbrGuest amenities include complimentary Wi-Fi, a washer/dryer, and parking for four cars in the driveway.brbrPlease note the bonus area is adjacent to a stairwell, and may not be suitable for small children.brbrTHE LOCATIONbrbrPedal to the Cape Cod Rail Trail in 0.2 miles; this paved and picturesque 25-mile pathway runs from South Dennis to Wellfleet and travels through the heart of Orleans.brbrSkaket Beach is less than a mile from home. Or visit the Cape Cod National Seashore, only a 5-mile car ride away.brbrWalk to The Jailhouse Tavern in 10 minutes for dinner and live music. Make a reservation at Abba and dine on inventive cuisine, or try out the tasty dishes at The Beacon Room —both just a 10-minute walk from your door.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Beautifully Remodeled Classic Beach Home on Cape Cod Rail Trail

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$365.52

Nauset Beach BuddybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrJust steps from Nauset Beach, this private garden-level apartment offers a cozy, walkable home base for a relaxed Cape Cod stay. Skip the beach parking and fees. Walk down for a swim, come back for lunch or a rest, then head out again when you’re ready. Early mornings at Nauset are especially peaceful and a favorite for many guests.brbrBuilt by hand by our father and grandfather, this home has been in our family for generations. We grew up spending summers here and now return with our own children. We hope you feel the same Cape Cod magic that has meant so much to us.brbrThe apartment is well-maintained and designed for simple, everyday comfort. It’s ideal for guests who value location, practicality, and classic New England charm. The kitchen features original wooden cabinetry and a traditional layout focused on function. The living area includes an Apple TV for streaming with your own accounts.brbrAs a lower-level space, dehumidifiers help maintain a comfortable indoor environment. An outdoor rinse area with a showerhead is available for washing off sand, though it is not fully private.brStandard bath linens are provided, along with beach towels, beach chairs, and games.brbrYou’re also well located to explore Orleans and the surrounding Cape. Restaurants, ice cream shops, grocery stores, kayak and bike rentals, and the Cape Cod Rail Trail are within a 10 to 15 minute drive. Skaket Beach, Crystal Lake, Wellfleet, and Hyannis are all easy to reach. The apartment has its own private entrance and is part of a property that also includes a separate upper-level home. brbrFor larger groups, book the whole home with Nauset Beach Getaway/brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Charming home within walking distance to Nauset Beach and National Seashore

Orleans, Massachusetts, United States

Bed

1

Bath

Sleeps

$1606.81

Welcome to Tito’s and Water — a luxurious waterfront retreat on Pleasant Bay. This stunning home features a main house with an attached carriage house/in-law suite offering extra privacy. With elegant interiors, multiple gathering spaces and a private dock, this home perfectly blends comfort, style, and coastal charm.brbr- 2 min drive to South Orleans Beachbr- 3 min drive to Wequassett Resort & Golf Clubbr- 10 min drive to The Captains Golf CoursebrbrKEY FEATURES:brbr☀ Beautiful water views of Pleasant Baybr☀ Less than 1 mile to Wequassett Resortbr☀ Sleeps 10; 7 bedrooms, 10 bedsbr☀ 4 full bathrooms + 2 half bathroomsbr☀ Private dock br☀ Carriage house (attached) with 2 bedrooms, living room, kitchenette & deckbr☀ Fully equipped and spacious chef's kitchen br☀ Indoor dining + outdoor dining areas seats 10 guestsbr☀ Outdoor kitchen with grill + pizza ovenbr☀ Spacious patio with cozy firepit + large TVbr☀ Gorgeous living room with modern décor, natural light & fireplacebr☀ Office with desk, monitor + stunning sea viewsbr☀ Two washer and dryers br☀ Air conditioning br☀ Coffee barbr☀ Large yard overlooking the water with corn hole br☀ Outdoor shower brbrHere Are A Few Kind Words From Our Past Guests:brbrWe had the most wonderful stay at Tito’s and Water! This home is beautiful and spacious. It was spotless and well taken care of. The location was perfect for our families, which included four children. The water view was amazing and extra stunning with the morning sunrises. Lucia, our host, was incredibly quick to respond to any of our questions and concerns. We wouldn’t hesitate to book again. - PamelabrbrI cannot describe enough how beautiful this home is. It's beyond gorgeous, and each and every design element, fitting/fixture, furniture detail is top quality, thoughtful and detailed. We were a group of 8 adults and loved our time here. Given it was in the middle of a winter storm, we stayed indoors quite a bit and enjoyed the many rooms in the home and the amenities within the home. I'm sure the place would be a different extreme of gorgeous during the summer season, with the water body across the road. Lucia and her team were extremely responsive, offering local suggestions, helping out when we needed additional home supplies (despite it being Christmas day), and so pleasant to interact with... - Snigdhabrbr☆☆ BEDROOMS ☆☆brbrThis gorgeous estate accommodates 10 guests across 7 beautifully appointed bedrooms:brbrMain House: brbr1st Floor:br- Bedroom #1: (Primary): King bed + TV + dresser + ensuite bathroom + walk-in closet + water views br- Bedroom #2: King bed + fireplace + dresser + full mirror + connection to a full bathroombrbr2nd Floor:br- Bedroom #3: King bed + closet + water viewsbr- Bedroom #4: Twin bed + seating area + small closetbr- Bedroom #5: Four twin beds (perfect for kids or group) + seating areabrbrCarriage House/In-law Suite (attached):brbr- Bedroom #6: King bed + dresser + closetbr- Bedroom #7: Queen bed + closetbrbr☆☆ BATHROOMS ☆☆brbrThere are four full bathrooms and two half bathroom in this home, each of them stocked with all the essentials you need for the duration of your stay including shampoo, conditioner, body wash, hand soap, blow dryers, and towels.brbrFirst floor:br- Bathroom #1: Full bathroom - ensuite in the primary bedroom with a shower. br- Bathroom #2: Full bathroom - walk in shower (entrance via bedroom + hallway)br- Bathroom #3: Half bathroombrbrSecond floor:br- Bathroom #4: Full bathroom - shower with tubbr- Bathroom #5: Half bathroombrbrCarriage House: br- Bathroom #6: Full bathroom - walk in showerbrbr☆☆ KITCHEN & LOUNGE ☆☆brbrKitchen: A chef’s dream! Fully equipped with sleek modern appliances, cookware, utensils, and a coffee bar with Keurig. The kitchen flows into a beautiful dining area perfect for family meals. There is also a kitchenette in the carriage house with essentials for a quick brew or light meal.brbrDining Room: Stylish indoor dining table for family meals that can seat 10 guests + separate carriage house dining table with a deck and waterviews. brbrLiving Room: Situated on the main level, the spacious living room features comfortable seating, a smart TV, a fireplace, piano, and abundant natural light through large windows showcasing water views.brbrOffice: Located on the second floor, with desk, chairs, monitor, and panoramic sea views – ideal for remote work or quiet reading.brbrSecond Floor Bedroom/Lounge: features a bright and comfortable living space adjoining the room with four twin beds — complete with a seating area and plenty of natural light. It’s a great spot for reading, relaxing, or enjoying a bit of privacy from the main living areas.brbrLaundry: Laundry room on 2nd floor + a washer/dryer located in the 1st floor hall. brbr☆☆ OUTSIDE SPACE ☆☆brbrThe exterior area of this home offers a private retreat with breathtaking views of Pleasant Bay.brbrMain Patio: Large entertaining area featuring a cozy firepit lounge, large outdoor TV, comfortable seating, and corn hole game. brbrSide Terrace: Located on the side of the home, this inviting area includes a dining table with seating for 10 guests, comfortable seating, and an outdoor kitchen with grill, pizza oven, and prep space.brbrPrivate Dock: Direct access to Pleasant Bay with panoramic water views. brbrCarriage House Deck: Cozy deck with seating for two guests off the carriage house living room.brbr☆☆ THINGS TO NOTE ☆☆brbrThe garage is off limits to guests and will be locked during your stay. brbrThis is a treasured family home that we are excited to share with guests! Please know there is a gallery wall in the upstairs hallway that connects the bedrooms and office that has some personal family photos. We hope you don't mind that we didn't take this personal touch down. brbr☆☆ HOUSE RULES ☆☆ brbr- No events or parties.br- No more than 10 guests max allowed at the home. br- No more than 4 children under 16 years old allowed at the home. br- No pets. br- No smoking. br- Quiet hours: 10pm-8am br- No food or drink other than water in the living areas or bedrooms. br- This is a private family home, please be respectful. brbr☆☆ PROXIMITY TO ORLEANS BEACHES ☆☆brbr- Pleasant Bay – steps away (for views and water access)br- South Orleans Beach – 2 min drivebr- Jackknife Beach – 4 min drivebr- Nauset Beach (Orleans) – 10 min drivebr- Hardings Beach (Chatham) – 12 min drivebr- Lighthouse Beach (Chatham) – 15 min drivebr- Skaket Beach – 10 min drivebrbr☆☆ NEARBY PLACES IN ORLEANS & CHATHAM ☆☆brbr- Downtown Orleans shops & cafésbr- Cape Cod Rail Trail (bike path)br- Rock Harbor Marinabr- Hot Chocolate Sparrow (local favorite café)br- The Knack (casual seafood & burgers)br- Mahoney’s Atlantic Bar & Grillbr- The Beacon Roombr- The Lobster Claw Restaurantbr- Chatham Bars Inn & Wequassett Resort (luxury dining & spa options)br- Chatham Village Market Grocery Storebr- Del Mar Bar & Bistrobr- Viera on Mainbr- Impudent Oysterbr- Sweet Tomatoes Pizzabr- Bluefins Sushi & Sake Barbrbr★★★ Book Today & Let Us Take Care Of You In Orleans! ★★★

NEW Luxury Waterfront – Firepit, Dock & Bay Views

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$416.67

Nauset Beach DreambrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrJust steps from Nauset Beach, this upper-level Cape Cod cottage offers a relaxed, walkable home base for an easy family vacation. Skip beach parking and fees — enjoy morning swims, midday breaks, and peaceful early strolls along the shore whenever you like.brbrThe home is comfortable and well cared for, featuring classic Cape Cod charm with original wooden cabinetry, a practical eat-in kitchen, and a bright living room with cozy seating and Apple TV for streaming. Guests also enjoy access to the shared patio and yard, perfect for unwinding after a day at the beach.brbrBeach towels, chairs, family games, and standard bath linens are provided to make your stay easy and enjoyable.brbrBuilt by hand by our father and grandfather, this family home has welcomed generations of summer memories. We hope you experience the same Cape Cod magic during your stay.brbrConveniently located near Orleans shops, dining, grocery stores, kayak and bike rentals, and the Cape Cod Rail Trail (10–15 minute drive). Easy access to Wellfleet, Hyannis, Skaket Beach, Crystal Lake, and more.brbrPlease note: The upper level is part of a property that also includes a separate lower-level apartment with its own private entrance. Both units can be rented together for larger or multi-generational groups.brbrHouse RulesbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.mbrAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

2nd floor Cottage, Oceanview, Deck, Shared Grill, & Outdoor Shower

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$1031.8

East Orleans Contemporary Cape Classic with Heated PoolbrRents Friday to Friday during peak seasonbrLinens Included, Beds MadebrPool operational from Memorial Day to Columbus Day.brbrbrTo view a slide show with captions, click on icon in upper right corner of the photo.brBe sure to click on the Virtual Tour tab for a 3-D tour of the property!brOr click HERE to watch a videobrbrNestled on almost a full acre in an upscale section of East Orleans, this property checks all the boxes for your idyllic summer family vacation. brbrConsider the location. You can walk 10 minutes to Meeting House Pond, a good sized quiet and beautiful inlet that offers fishing and charter boat tours. Launch your kayak here and paddle around the pond or head up the channel to Pleasant Bay -- or for more ambitious yakkers -- all the way out to Chatham Harbor. The property provides two kayaks for guest use.brbrFrom the house, a slightly different 10-minute walk brings you to East Orleans Village. Here you'll find intriguing restaurants and shops. The Village is your perfect after dinner outing for ice cream! If you're like most vacationers in this part of Orleans, you'll become hooked on Nauset Farms, a local market acclaimed for its butcher shop, gourmet desserts and exceptional deli sandwiches to go.brbrUnless you've pledged to park the car at the property and not drive much of anywhere for your vacation (understandable), you may want to cruise about five minutes into Orleans Center for an alluring variety of shops, restaurants, galleries, Cape League baseball and more. Or drive five minutes in the other direction for the beach experience so many come to the Cape for: big and sandy Nauset Beach, one of the best on the east coast.brbrThis custom designed and built home has been featured in Early American Life magazine for its traditional design modernized for todays living and comfort.brThis home's 2,500 square foot interior offers an intriguing blend of classic and progressive, best described as “White & Wood.” Wide board wood flooring, exposed wood beam ceilings and wood paneling up to chair rail height all work in delightful contrast with white walls, cabinets and lots of glass all around to create a timeless, yet cutting edge impression.brbrThe beautifully renovated kitchen with granite counters is fully equipped and ready for action. There's a charming dining room with seating for eight, but you may elect to serve meals at the umbrella shaded table poolside. You'll be delighted by the multiple lounge seating areas in this house, so your group of up to eight can be comfortably together or break off into smaller gatherings and not be on top of each other. brbrThe media room features a newly installed Crate and Barrel sectional with 48”x48” glass coffee table with a new Samsung 65” Smart “Frame” TV along with light blocking window shades.brbrThe Great room overlooking the pool features newly Installed, Kingsley Bates three piece sectional and two piece day lounger along with a Crate and Barrel Rattan accent chair to complete seating arrangements.brbrThere are four bedrooms, including the king primary on the main level with its full en-suite bathroom newly and beautifully renovated in 2024 with heated floors . In addition there is a 43” Samsung “Frame” smart TV.brbrThe upper level presents the other two bedrooms, each of the first two with a full size plus a twin. The final fourth bedroom is a studio over the garage with access via a separate stairway. It has a full bath en-suite and its own kitchenette. Here you'll find a comfortable Queen size bed and seating to watch TV.brbrThere are three full baths in the house, one on the main level, the other two upstairs. All the baths have been recently renovated and make a sparkling impression. brbrThe 950 square foot granite pool patio has four sling type loungers along with a teak dining table with seating for six covered by a 10' bamboo umbrella.brbrThe focus is naturally on the inviting in-ground heated, saltwater pool and its appealing patio with lounge seating. When you've had enough sun, the spacious screened porch provides a shady and spacious option, overlooking the pool and grounds.brbrThe home is cooled by the combination of a central air conditioning system plus a whisper quiet GE profile window unit for the studio. There is Smart TV and high speed Wi-Fi with google mesh Wi-Fi extenders for maximum Wi-Fi coverage throughout the home. There is also an enclosed outdoor shower and a gas grill.brbrPlease enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 215.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.brbrThis property offers a three-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived.brbrBe sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod.brbrIt's your vacation. Get Picky! ®

Sea Mist: 029-OS Contemporary Cape Classic with Heated Salt Water Pool

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$407.94

Gray GablesbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWhat We LovebrClassic Cape Cod charm and a convenient location within walking distance to nearby natural landmarks are yours at this historic, 1840 home. Nestled on over an acre of land set away from the main road, the home offers an abundance of peace and solitude for your stay. The property backs up to 33 acres of conservation land that features walking trails around two ponds. A good walk down to the end of the road will bring you to Nauset Inlet where beautiful vistas are waiting to award your trek. Nauset and Skaket Beaches are also within easy reach of the home. Two gigantic shade trees provide a pleasant setting for outdoor gatherings, with yard games provided for added entertainment. The six-person dining table on the deck sets the stage for alfresco meals. When you're ready to explore a little, you'll find East Orleans eateries, downtown Orleans, and access to the Cape Cod Rail Trail all within a two-mile radius.brbrThe inviting interior exudes a homey ambiance, with traditional decor and original features accenting the home's historic style. The massive full kitchen boasts a full suite of updated stainless steel appliances to help you handle family-style feasts with ease. A smart TV and board games are ready to welcome additional home entertainment in the living room.brbrHouse RulesbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide byour good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 4 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Gray Gables | House in Orleans

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$299.4

Saltwater HavenbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrDiscover ultimate relaxation and plenty of beachside fun with this idyllic, multi-level Orleans home, nestled into the picturesque Cape Cod scenery and boasting fantastic amenities.brbrIdeally located just a mile and a half from Nauset Beach enjoy boating, swimming, or basking in the breathtaking views, as well as Skaket Beach (three miles) nearby. Delight in walking to East Orleans Center (half a mile) for shopping, artist's cottages, Nauset Farms, great coffee shops, and local ice cream. The Academy Playhouse and Eldredge Park are just a bit further out. You’ll also find Chatham Lighthouse and Cranberry Valley Golf Course 11 miles away.brbrInside this retreat, feel right at home snuggled up on the plush sofa while streaming your favorite movies or relaxing by the fire with a good book. The bright interiors are bursting with elegant decor, charming accents (including a spiral staircase!), and lots of natural light making a perfect backdrop for gathering with loved ones. Craft delicious home-cooked meals in the stylish kitchen, or have a barbecue while sipping some local brews in the sunshine. The spacious wooden deck invites you to kick back and watch the sunset while creating unforgettable vacation memories. A private washer/dryer and an outdoor shower round out the list of this home’s stellar perks.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brThe property caretaker permanently resides in the lower unit.brThe staircase is spiral to access upstairs.brStreaming available on guest credentials.brThree vehicles maximum are permitted at this home.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Tranquil & sunlit home with peaceful yard, large deck, & fireplace - near beach

Orleans, Massachusetts, United States

3

Bed