Vacation Rentals By Owner In Orleans, MA

$775.35

Orleans Cape Cod, 3BR, Fire Pit, Central AC, 8 Min to Nauset Beach, Sleeps 10

Orleans, Massachusetts, United States

Let the Cape Cod breeze clear your thoughts and the sound of birdsong reset your pace. This recently renovated Orleans retreat sits on a quiet wooded lot — walk 5 minutes to private Pilgrim Lake, stroll through the woods to Arey's Pond and Pleasant Bay, or drive 7 minutes to Nauset or Skaket Beach.brbrTwo distinct living rooms, a designer coffee bar, a chef's kitchen, and a private backyard oasis with firepit and grill make this the Cape Cod home your group will talk about all year. Sleeps up to 10. Trupti (your host) is local, responsive, and genuinely invested in making your stay exceptional.brbrTHE HOMEbrbrRecently renovated and thoughtfully designed for groups and families, this 3-bedroom Orleans retreat gives everyone space to gather, unwind, and make memories. Two distinct living rooms, a designer coffee bar, a chef's kitchen, and a private backyard oasis mean your group will never run out of places to be. Trupti (your host) is always just a message away.brbr---brbrLIVING ROOM 1 — THE GREAT ROOMbrbrThe heart of the home is a bright, open-plan great room where the living area, dining room, and kitchen flow effortlessly into one another. Oversized windows on two walls flood the space with natural light and frame the surrounding New England woodland. Large comfortable sofas and accent chairs seat your whole group in one place, a decorative fireplace adds warmth and character, and a large Smart TV is ready for movie nights. The open layout means whoever is cooking is never cut off from the conversation.brbrLIVING ROOM 2 — THE SITTING ROOMbrbrA second fully furnished sitting room gives your group a quieter space to retreat when the main room is lively — perfect for reading, working, or simply unwinding. It has its own distinct character, decorative fireplace, and Smart TV. An Orleans coordinate sign and framed Cape Cod nautical chart make it feel exactly like where you are.brbrTHE COFFEE BARbrbrA dedicated coffee bar that guests genuinely love:br- Cuisinart coffee makerbr- Monin flavoring syrups (vanilla, caramel, and more)br- Ceramic mugs on a wooden serving traybr- Open shelving stocked with wine glasses and cocktail glassesbr- Full water carafe set for the tablebrbrNo hunting through cabinets — everything is out, organized, and ready. Your morning routine, upgraded.brbrTHE KITCHENbrbrStocked the way a chef would want it:br- Farmhouse sink + stainless steel appliancesbr- Butcher block island with 4 bar stoolsbr- Subway tile backsplashbr- Lobster pots, stovetop griddle, cast iron, sharp knivesbr- Full spice rack, blender, and quality cookware throughoutbr- New round dining table seats 6–8 under original pendant lightsbr- Fresh herb garden (seasonal) just outside — yours to usebrbr---brbrBEDROOMS — SLEEPS UP TO 10brbrEvery bedroom has quality linens, blackout shades, closet space, and ample storage — everything you need to rest and recharge on vacation.brbr- Bedroom 1 (first floor): King bed — ideal for couples or guests who prefer no stairs. Easy access to the first floor full bath.br- Bedroom 2 (second floor): King bed + trundle that opens to 2 twin beds — designed for families with young children.br- Bedroom 3 (second floor): 2 twin beds + trundle with 2 additional twins — great for kids, teens, or a friend group.brbrBATHROOMSbrbr- First floor: Full bath with tub, toilet, and sinkbr- Second floor: Full bath with shower, toilet, and sinkbr- Outdoors: Private outdoor shower — rinse off after the beachbrbr---brbrOUTDOOR LIVINGbrbrOne of the finest private backyards on the Lower Cape:brbr- Patio: Outdoor sofa sectional, lounge chairs, umbrella, and dining table — surrounded by blooming Cape Cod hydrangeasbr- Grill station: Built-in gas grill with generous counter space for outdoor cooking and entertainingbr- Firepit: Stone firepit with 6 Adirondack chairs on a dedicated gravel pad — s'mores kit included (graham crackers, chocolate, marshmallows, and skewers)br- Cornhole and yard gamesbr- Private outdoor showerbrbrThe yard is wooded, private, and peaceful. No neighbors crowding you.brbrBASEMENT GAME ROOMbrbrRainy day No problem:br- Foosball tablebr- Ping pong tablebr- Shuffleboardbr- Board games, puzzles, and card games for all agesbrbrDEDICATED WORKSPACEbrbrA proper desk setup with monitor and fast Wi-Fi — ideal for remote workers blending work and vacation on the Cape. Long-term stays welcome.brbr---brbrBEACH + NATURE ACCESSbrbr- Pilgrim Lake (5-min walk): Private association beach on a freshwater lake — swim, kayak, or paddleboardbr- Arey's Pond (wooded walk): A winding woodland path leads to a saltwater pond on Pleasant Bay — walk, bike, run the trails, or rent kayaks from Arey's Pond Boat Yard and paddle into Pleasant Baybr- Nauset Beach (7-min drive): Oceanside — one of the best on the Capebr- Skaket Beach (7-min drive): Bayside, calm water — perfect for young children and golden hour sunsetsbr- Cape Cod Rail Trail: Nearby access for scenic biking and runningbrbrBeach chairs and coolers available for guest use. Pack lighter.brbr---brEXTRASbrbr- Central AC and heatingbr- Washer/dryer in basement laundry roombr- Smart TVs throughoutbr- Keyless entrybr- Parking for 3 cars in driveway (no street or lawn parking)br- Fast Wi-Fi throughoutbr- Not pet-friendly (Unfortunately, we cannot accommodate pets due to allergies)brbrMID-WEEK SUMMER STAYS — A SMARTER WAY TO DO THE CAPEbrbrOne of the best-kept secrets about staying in Orleans: book Monday to Friday in June, July, or August, and you completely avoid Cape Cod bridge traffic — both ways. Arrive Monday morning when the roads are clear, enjoy five full days on the Cape at its most relaxed, and head home Friday before the weekend rush ever starts. So you are never stuck in the Sunday exodus. Guests who discover this never go back to weekend bookings.

Bed

Bath

Sleeps

Select Dates for Price

Private Vacation Home

Fabulous Family CapeHouse, with Views, Beach & Dock! Gatherings Inside and Out!

Orleans, Massachusetts, United States

brbr*Now Open June 5-19, 2026, Perfect Relaxing Off-Season Cape Vacation!*brbrThis sprawling family beach home is perfectly located on a hilltop with 3.5 acres overlooking Pleasant Bay in South Orleans. This amazing home offers the comfort of a private neighborhood and is just steps to the association beach and dock! brAltogether, this beautiful home comfortably sleeps 14-16 and provides two full kitchens and multiple separate living areas, offering plenty of space for everyone. The Main House features four bedrooms and a Finished Basement with bunk beds that can sleep 6, plus a ping-pong table, comfy seating, and ROKU HD TV, perfect for watching anything you want!brThe attached two-bedroom, two-bath Guest House, offers a second full kitchen and living area with amazing water views, a deck, and an en-suite master bedroom with a private balcony.brAdditional great features include the massive redwood back deck, offering ample space for gathering with friends and family, grilling after a busy day on the water, and the large, grassy front yard, designed specifically for all your favorite lawn games.brWe invite you to enjoy all the benefits of our home in the prestigious Quanset Harbor Club neighborhood, with a private beach and dock, just down the hill, 300 yards from the house. The beach is just right for an hour or two with little ones who need to take a nap, or you can settle in for a day filled with kayaking and sitting in the sun! (The beach is rocky, so beach shoes are a good idea!)brWe are centrally located in South Orleans, with easy access to Route 28, which will take you in whichever direction you are in the mood for. Turn right to head to East Orleans and ride the waves at Nauset Beach, or take a left towards picturesque downtown Chatham and Lighthouse Beach. This home is perfectly located for wedding weekends at The Wequassett Inn or the Winslow Estate, also in South Orleans. brPlease feel free to email me with any questions. This is a wonderful spot for a very chill and relaxing family vacation on the Cape!

Bed

Bath

Sleeps

$604.3

/ Nightly

Cottage

Captain's Quarters by Nauset Beach

Orleans, Massachusetts, United States

Captain's Quarters, brought to you by The Heart of Cape Cod, is a quintessential 3 bedroom Cape Cod cottage which is walking distance from the calm waters of Nauset Inlet (Priscilla's Landing) and famous Nauset Beach on the oceanside. Captain's Quarters cottage is the perfect home base for your classic adventure on the Cape. Come see what makes staying in Nauset Heights so special! brbrWe respect the autonomy of our guests but are available by text, email, phone, carrier pigeon, smoke signal, yodeling, or FacetimebrbrNauset Heights neighborhood is a small, quiet family neighborhood association surrounded by Nauset Inlet on one side and the Atlantic Ocean on the other. It is perfect for small families or small groups as it is quite the residential area.brbrNauset Heights is truly a special place. A walk down to Pleasant Bay to dig your toes in the sand and enjoy the quiet and calmer surf brings peace. A turn in the other direction will bring you to the ocean where one can bear witness to the haul out of seals, or the gannets diving at breakneck speeds into the surf, and if one is lucky, spot whales off the coast as they dive for deeper waters and show a massive fan of tail.brbrHere at Captain’s Quarters, you can enjoy your adventures on the Cape from Spring through Autumn with mini-split heating and cooling throughout. With three bedrooms, a fully stocked kitchen, bath, deck, charcoal grill, and even an outdoor shower, beach days and exploring are easy with our cottage as your base camp. Walk to Priscilla Landing, Nauset Beach, and Mill Pond. Hop in the car for a short little drive to our exquisite shops, gourmet foods, wine shops, and ice creameries or even another fantastic beach close by. National Seashore on your bucket list No problem! Each reservation comes with a complete guide to the best local’s insider tips and places to go, things to do, and places to see.brbrCaptain’s Quarters is a cozy 660 square foot cottage with three bedrooms. The master has a queen bed. Bedrooms two and three contain two sets of twins in each. The living room is outfitted with a couch, two reading chairs, and a small reading library and game table. A Roku tv is ready for you to login and pick up where you left off on your favorite streaming episodes. We are located between Nauset inlet and the Atlantic Ocean in beautiful Nauset HeightsbrbrHighlights include:brbr• A custom, state-of-the-art, award-winning house manual with recommendations is provided with each staybr• Quiet and calm beach days on Priscilla Landing or access Nauset Beach on the ocean side through the association br stairs and enjoy less crowdsbr• 5 Beds Total - 1 Queen, 4 Twin bedsbr• Luxurious linens, duvets, Turkish bath towel sets with charcoal infused bamboo wash cloths, and beach towels br provided (summer)br• 1 full bath/1 outdoor showerbr• Eco-Friendly amenities such as shampoo, conditioner, and body wash with no sulphates, phosphates, and no micro- br beads! br• Washer and dryer in basementbr• Coffee bar with drip coffee maker, French Press, hot water kettle, regular and decaf coffee and an assortment of teas br providedbr• Gas grill and patio furniturebr• Small reading library, blue tooth stereo, board games, corn hole, and game table providedbr• No pets. We have many pet friendly options for you to choose from, this is not one of them. Please do not “ask br anyway” (sorry but the answer will still be no)br• Strong WiFi throughoutbr• Many add-ons available such as Pack-n-Plays, Farm Fresh Eggs, Beach Games, Tours and more! Details provided after br bookingbr• Sandy toes and beach hair guaranteedbr• Professionally cleaned by an award-winning, VRMA recognized company that uses thorough checklists, followed by br sanitization and disinfection of high touch points throughout the home. brbrAs always, we recommend purchasing your own travel insurance to safeguard your vacation.brbrFor Airbnb: A quick note on who you are paying for what, because lately everyone asks some version of who am I paying for what and to who. We set two things. One. The nightly rate for the home itself which we keep as fair as possible for this area. Two. The cleaning fee matches what our professional cleaning company charges to clean and reset a home this size. Those are the only amounts we control. Airbnb collects its own platform service fee for using the Airbnb site and support. Airbnb may include that platform fee in the total price you see here instead of showing it as a separate line which can make it look like it is part of what we charge. It is not. That amount goes to Airbnb. You will also see taxes as a separate line. Those taxes are required by state and local rules for this area. We do not set the tax rates, and we do not keep those funds. Airbnb calls this “fee transparency”.brbrbrbrCommunication with guests is important to us. Please be sure you have app notifications turned on for your phone as this will be our means of communicating with you before, during, and after your stay. Our digital guidebooks contain directions, instructions, and access information. It is your responsibility to review this information prior to arrival.

Bed

Bath

Sleeps

$632.05

/ Nightly

Private Vacation Home

Central AC Close to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15550 - Mainsail: Central AC Close to Nauset Beach!brbrbrbrThe Space:brbrWake up, take a quick stroll down Main Street, grab some coffee at Whisk, sandwiches at Nauset Farms, then head just 1 mile to Nauset Beach by bike or car, or even walking if you’re up for it, and enjoy this amazing Orleans location! Within walking distance to several restaurants and stores (Whisk, Nauset Farms, Barley Neck Inn, The Rail…) this home is a great option for those who like to travel by car and on foot, and offers great access to nearby amenities. Located at a midway point on the Cape so its easier to visit places like Chatham or Ptown for the day. Head directly west from the home and you’ll find Skaket Beach, which offers a bayside beach option for those who prefer the warmer, calmer bay waters.br br Back at the home, the large yard and deck area is perfect for enjoying the outdoor space, with a gas grill, outdoor shower, and seating. Inside the clean and newly furnished home is a great place to relax. With central air, you’ll stay cool in this home even during the hottest of days. The first floor offers a semi-open floor plan with the kitchen, dining, and living area all in close proximity, which provides a great place for everyone to gather. The light-filled living area provides plenty of comfortable seating, and a flatscreen TV.brbrbrbrThe right side of the home, on the first floor, offers two bedrooms; one has a queen bed, and the other has a twin bunk bed plus a twin single. The first floor also has a full bathroom, which has convenient access from both bedrooms. Upstairs, a large bedroom with a king size bed offers plenty of space, and the bedroom adjacent has one queen and two twin beds. Between these upstairs bedrooms is another full bathroom. A beachgoers paradise, this great Orleans location is sure to please the biggest of beach bums, and the nearby amenities make staying at this home feel like a true Cape Cod vacation!brbrbrbrHome Details:brbr-Sleeps 10brbr-2nd Floor Bedroom #1: 1 King Bedbrbr-2nd Floor Bedroom #2: 1 Queen Bed, 2 Twin Bedsbrbr-1st Floor Bedroom #1: 1 Queen Bedbrbr-1st Floor Bedroom #2: Twin Bunk Beds (2 twins) + 1 Twin Bedbrbr-Central A/Cbrbr-Fireplace is NOT for guest usebrbr-WiFibr-Cable TVbr-Gas Grillbr-Walk to Townbr-Deck with Furniturebr-NO Pets (fines remitted)br-Outdoor Showerbr-Private Yardbr-2 Miles to Nauset Beachbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0408462240brbrbrbrThe Neighborhood:brbrOceanside

Bed

Bath

Sleeps

$1035.77

/ Nightly

Private Vacation Home

Walk to Rock Harbor Beach from your spacious Orleans coastal retreat

Orleans, Massachusetts, United States

Spacious Orleans Home Near Rock Harbor – Ideal for Families & GroupsbrbrWelcome to your Cape Cod escape! This spacious 5 bedroom, 2-bath Orleans home is perfectly located just a short stroll from Rock Harbor, one of the Cape’s most iconic spots for breathtaking sunsets, fishing boats, and tidal flats. Designed for comfort and convenience, the house easily accommodates up to 10 guests and offers everything you need for a memorable vacation.brbrProperty Highlights:brSleeps 10 comfortably across 5 bedroomsbr2 full bathrooms plus a refreshing outdoor showerbrBright and open living room with comfortable seating and smart TVbrFully equipped kitchen with modern appliances, cookware, and dining essentialsbrLarge dining table for family meals and game nightsbrPortable air conditioners in 3 out of the 4 bedrooms upstairs and main living area downstairs for summer comfortbrHigh-speed WiFi throughout the homebrbrOutdoor LivingbrAfter a day at the beach, relax in the private yard or gather on the patio with comfortable seating. Fire up the BBQ grill for an outdoor cookout, or enjoy the quintessential Cape experience of rinsing off in the outdoor shower, and enjoying S'mores from the new firepit. The yard has plenty of space for kids to play while adults unwind. Driveway parking is available for multiple vehicles.brbrLocation – The Best of Cape Cod at Your DoorstepbrRock Harbor Beach – Just a walk away, known for stunning sunsets and calm bay waters.brSkaket Beach – A few minutes by car, offering warm waters, tide pools, and family-friendly swimming.brNauset Beach – On the Atlantic side, perfect for surfing, boogie boarding, and long beach walks.brCape Cod Rail Trail – Nearby access to miles of biking and walking through scenic woodlands and towns.brDowntown Orleans – Shop local boutiques, visit art galleries, enjoy ice cream shops, and dine at Cape favorites like Land Ho! and the Lobster Claw.brbrLocal Activities & AttractionsbrCharter a fishing trip directly from Rock Harbor.brEnjoy kayaking and paddleboarding right from the backyard into Rock Harbor, at Town Cove, or along Skaket Beach.brExplore the Cape Cod National Seashore, with miles of trails and unspoiled coastline.brTake a day trip to Chatham, Wellfleet, or Provincetown for shopping, dining, and culture.brFamily fun nearby with mini golf, go-karts, and local theaters.brbrGuest ExperiencebrGuests consistently rave about the location, the space for families and groups, and the balance of Cape Cod charm with modern conveniences like WiFi, streaming TVs, and portable A/C units. Whether it’s gathering around the dining table, grilling outside after the beach, or watching the sunset at Rock Harbor, this home makes vacation memories effortless.brbrPerfect For:brFamily vacations – Space for everyone and beaches kids will lovebrFriends’ getaways – Easy access to restaurants, nightlife, and outdoor adventuresbrExtended stays – Comforts like laundry, WiFi, and a fully stocked kitchenbrbrYour Cape Escape AwaitsbrFrom lazy mornings with coffee on the patio to days filled with beaches, biking, and exploring Orleans, this Rock Harbor home is the ideal base for your Cape Cod adventure. Discover why guests return year after year to enjoy this unique spot where comfort meets coastal charm.brbrCheck out the aerial views of our home and rock harbor https://vimeo.com/1196298392 share=copy&fl=sv&fe=ci

Bed

Bath

Sleeps

$2231.46

/ Nightly

Private Vacation Home

A Wave From It All: 227-O Overlooks Nauset Beach/Atlantic, Heated Pool, Hot Tub & Fire-pit

Orleans, Massachusetts, United States

This home is professionally managed by Pretty Picky Properties brbrGrand Villa Overlooks Nauset Beach & the Atlantic, Heated Pool, Hot Tub & Gas Fire-pit!brbrRents Friday to Friday brOff-season partial weeks available.brSleeps 14 brLinens Included/Beds MadebrPool and hot tub are open Memorial Day - Columbus DaybrbrYour group of up to 14 will vacation in style at this superb ocean side manor house at famous Nauset Beach in East Orleans. The stunning location provides panoramic views of the beach and ocean from both levels of the house. And you have a very short walk to the beach. The property also features a 36'x18' heated pool, hot tub and gas fire pit!!brbrThe spacious, social, fully loaded kitchen anchors the main level and includes a breakfast bar with high boy seating for four. A few steps away, the large dining room easily seats 10 and can accommodate more. Relax in the exquisite living room with lounge seating and a large flat screen TV. This home has Sonos sound system off the back deck and in the lower level living space. It is centrally air conditioned and has hi-speed Wi-Fi and cable TV.brbrA large, covered patio is just off the living room, with a dining table and chairs, plenty of lounge seating and views of the Atlantic. A separate lounge/bar room offers a wet bar with fridge, another TV, and bar seating for three. Walk out from there to a beautiful, hexagonal screened porch which leads to the pool deck.brbrThere is one bedroom on the main level, a roomy primary suite with a King size bed and full bath en suite with a walk in shower. The main level also includes a half bath and quiet den/study to serve as your work station, if necessary.brbrOn the upper level, you'll first encounter another lounge area, which walks out to the upper deck that presents 180-degree breathtaking views of Nauset Beach and ocean. Comfy lounge seating here too, including a king-size super comfy sleeper sofa.brbrOn this level, you'll find four more bedrooms. There's a second, oversized primary suite, with a king size bed plus twin day bed with a twin trundle below. There is a full bath en suite, of course. Another bedroom suite features a King size bed and private full bath. Bedrooms #4 and #5 can be closed off to create a two-bedroom suite. Both bedrooms feature a queen size bed with a standard twin bed and twin trundle bed. The two bedrooms share a full bath between, Jack & Jill style.brbrThe lower level of the home houses an extraordinary full home theater with a projector, 10-foot screen and luxurious lounge seats with cup holders for up to 12, plus giant bean bag seating for more. What an amazing place should the weather not cooperate or for your evening entertainment. Also on this level: a workout room, a ping pong table, and a half bath. There are four full and two half baths in all.brbrThe yard and grounds provide plenty of space for kids to play safely. There is also a gas grill and horseshoe pits to keep everyone entertained.brbrConsider planning your summer vacation at this truly remarkable property in one of Cape Cod's most coveted locations.brbrPlease enter in your travel dates in top right corner of this page 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 17.45%.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! ®

Bed

Bath

Sleeps

$573.33

/ Nightly

Private Vacation Home

East Orleans Waterview Getaway

Orleans, Massachusetts, United States

Immaculate home sleeps 6 in a private location with beautiful water views. Tastefully decorated and spotless, this 1600 square foot home has a king bedroom and queen bedroom on the main level and a loft space with a queen and double beds. The main level includes a sunny fully equipped eat-in kitchen with quartz counters that leads to the living room w/sliders to the large patio. After a day at the beach, enjoy a perfect Summer evening grilling out on the patio and relaxing by the water. Minutes to Nauset Beach and Meeting House Landing for Kayaking and Boating. Mini-Split AC system & Enclosed outdoor shower. No direct water access.brbr***Owner will consider 1 dog - Please include dog details with your inquiry so that we can confirm with owner. Thank you! No cats unfortunately.***

2

Bed

1

Bath

6

Sleeps

$532.76

/ Nightly

Private Vacation Home

Association Access to Skaket Beach

Orleans, Massachusetts, United States

***PRE-SUMMER SPECIAL***WEEK OF JULY 19 - 26, 2026***JUST REDUCED $550***brbrExceptional home close to Skaket Beach in Orleans. brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrThis vibrant and tastefully decorated home is located approximately 1/2 mile from the private beach access. This well-maintained property has been recently renovated with sophisticated fixtures, meticulously selected furniture, fresh new paint, a stylish patio, and extensive new landscaping. These owners have a fine eye for detail to make sure their tenants have a wonderful vacation. brbrThe first level of this home offers an inviting open kitchen, dining area, and living room with vaulted ceilings and a majestic color palette, one bedroom with a queen bed, one bedroom with two twins, a full bathroom with tub and a beautiful sun porch. brbrThe second floor has a substantial master bedroom suite with a king bed and private bath. This home is conveniently located close to the bike path and Orleans center. brbrAmenities include Dishwasher, Washer and Dryer, Wireless Internet, 2 Televisions with Cable, 4 Built-in Wall Air Conditioning Units, Gas Grill, and an Enclosed Outdoor Shower. brbr* Additional Fees: $220 non-refundable reservation fee; $30 damage protection fee (no security deposit required); guest services fee; all applicable taxesbr* FREE WIFIbr* SUNDAY TO SUNDAY RENTALbr* NO PETSbr* NO SMOKINGbr* OCCUPANCY: 6 (Adults and children)br* PARKING FOR 4 VEHICLESbr* SHEETS AND TOWELS ARE NOT PROVIDED, available to rent from local linen company, we are happy to provide informationbrbr**** FREE ACTIVITIES INCLUDED ****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrAs a guest of Kinlin Grover Compass, you'll receive free tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities! Activities and availability are subject to change. Not available on stays over 28 days.brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.brbrKGC OMCGR

Bed

Bath

Sleeps

$449.79

/ Nightly

Cottage

Charming 2-bedroom cottage in wonderful Barley Neck area of Orleans with WiFi AC

Orleans, Massachusetts, United States

Charming cape cottage, 2 large bedrooms, oversized eat in kitchen, full bath, spacious living room with desk. A huge, sunny deck and screened porch. Outside shower and patio with grill. Play space in the yard.

Bed

Bath

Sleeps

$1133.01

/ Nightly

Private Vacation Home

Large House w/ample space- steps from Skaket Beach, close to CCRT and downtown!

Orleans, Massachusetts, United States

This spacious, newly renovated home offers plenty of room for everyone to relax. Just steps from Skaket Beach, no parking pass is needed to enjoy the stunning shoreline. The expansive backyard is perfect for outdoor games and relaxation, complete with toys and activities for all ages. Spend evenings cooking out on the brand-new deck, watching the sunset hues, or take a leisurely stroll with your favorite beverage along the famous Skaket Beach. Proximity to the Cape Cod Rail Trail, Hog Island Brewery, Rock Harbor, Nauset Beach, fresh water ponds, grocery stores, restaurants, coffee shops, and shopping!brbrThe upstairs features a well-equipped kitchen, living room, bathroom, enclosed porch, and a large second-story deck. brbrThe downstairs offers 4 bedrooms, closets, and a first-floor walk-out deck to the backyard. brbrThe basement offers an entranceway in from the driveway and room for bikes and storage.brbrSkaket Beach is just steps from the house and Hog Island is right around the corner.brbrThis home is a lifetime dream for us to attain and we are looking for renters that will enjoy the property the way we enjoy it for years to come.brbrIMPORTANT: Linens, (Sheets and towels) are not provided. There are a few services we recommend that provides sheets and towels.

Bed

Bath

Sleeps

$397.4

/ Nightly

Private Vacation Home

New construction home on quiet, private waterview lot near Pleasant Bay

Orleans, Massachusetts, United States

We will provide an additional $250 discount for singles or couples -- please send a message and we'll discuss how to implement. This is a cozy, immaculate, recently constructed home on a private half-acre lot with a tranquil, south-facing water view and outdoor shower in a quiet and upscale neighborhood. Main floor has open kitchen/dining/living room and queen bedroom/bath, with doors to huge deck. Downstairs consists of one walkout room with full bed and bath with windows on three sides and sliding doors to patio, outdoor shower and private yard.

Bed

Bath

Sleeps

$1661.35

/ Nightly

Private Vacation Home

Waterfront on Cape Cod Bay!

Orleans, Massachusetts, United States

Summary:brbr15538 - Bayside Bliss: Waterfront on Cape Cod Bay!brbrbrbrThe Space:brbrEscape to our waterfront sanctuary nestled beside Rock Harbor in Orleans. Delight in exclusive access to our private beach via a picturesque deeded path, bask in the sun on opulent chaise lounges adorning the wrap-around deck, and surrender to the allure of the most breathtaking sunsets over Cape Cod Bay.brbrMoments from town, culinary and recreational delights await, from leisurely bike rides along the Rail Trail to savoring the finest local brews at Hog Island Brewery. Indulge in gourmet delights from Main Street Wine & Gourmet and unwind in the comfort of our air-conditioned haven, adorned with stylish accents and premium amenities.brbrRelax in the sun-kissed living room beside a decorative wood fireplace, or indulge in culinary delights crafted in our fully equipped galley-style kitchen. Retreat to our elegantly appointed bedrooms, each a haven of tranquility and sophistication, offering plush bedding and modern comforts.brbrEntertainment abounds with a foosball table, board games, and the allure of a crackling firepit under the stars.brbrFor culinary adventures, indulge in the finest local flavors at Hot Chocolate Sparrow, Viv’s Kitchen & Juice Bar, or The Land Ho. With sheets and bath towels provided for every guest, and our home being dog-friendly, your stay promises to be a seamless blend of luxury and comfort.brbrSeize the moment and immerse yourself in the epitome of bayside bliss at our exquisite waterfront haven. Reserve your escape today and discover a world of coastal living on Cape Cod's pristine shores.brbrA Game Room is being added for the 2025 Season!brbrbrTraveling with a Large Group brCheck out our sister property just 300 feet away: 15519 - Bayview OutpostbrbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8br-2 Floors (Ground and 1st Floor)brBedroomsbr-Total: 4br-1st Floor Master Bedroom: 1 Queen Bedbr-1st Floor Bedroom #2: 2 Twin Bedsbr-Ground Floor Bedroom #3: 1 King Bedbr-Ground Floor Bedroom #4: 2 Twin BedsbrBathroomsbr-Total: 2br-Ground Floor: Full bathroom with tub/shower combobr-1st Floor: Full bathroom with showerbrOther Amenitiesbr-indoor wood fireplace is not for guest usebr-Mini-Split A/C System (Like Central Air)br-Cable/Streamingbr-Smart TV br-WiFibr-Foosball Tablebr-Washer/Dryer br-Gas Grill br-Fire Pit br-Deck with Furniturebr-Outdoor Showerbr-Waterfront on Cape Cod Baybr-Walk to Waterbr-Access to Private Beachbr-please note outdoor amenities are available seasonallybr-There is parking for a maximum of 4 carsbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-C0056932240brbrbrbrThe Neighborhood:brbrBayside

4

Bed

2

Bath

8

Sleeps

$368.35

/ Nightly

Private Vacation Home

The Salteen House New to the RENTAL market.Experienced Hosts.Great for Two Fams!

Orleans, Massachusetts, United States

We've been searching for a home on a cape for years and we finally found our dream house! We have two girls ages 13 and 12 brRecently purchased (hence no reviews)our cape house is located in Orleans - 3 miles for Skaket and 3 miles from Nauset. brGreat for two families - master bedroom upstairs with a king and trundle and private bath.two bedrooms on the first floor with a bathroom/ tub. brA cape house wouldn't be complete without an outdoor shower!brBook now and get a great deal.

Bed

Bath

Sleeps

$722.47

/ Nightly

Private Vacation Home

10-Minute Walk to Skaket Beach - Orleans - Bikes Included - Close to Town

Orleans, Massachusetts, United States

Welcome to your ideal Cape Cod vacation retreat! brbrLocated on a quiet cul-de-sac, approximately ½ mile from the beautiful Skaket Beach, this spacious 4-bedroom, 2-bath home is perfect for one or two families seeking to relax, explore, and create lasting summer memories.brEnjoy warm Bay swimming, tidal flats, snack bar, bathhouse, and unforgettable sunsets—all just a short walk away at Skaket Beach. Located only minutes from the beautiful town center for convenient grocery shopping, morning coffee, local restaurants, convenience stores, and more. brbrThe Home -br* Sleeps about 13 guests comfortably (standard occupancy 8; additional guests welcome with a fee)br* 9 beds (twin & full)br* Pet-friendly (up to 2 dogs)br* Kid-friendly, clean, and comfortablebr* Views of the marsh and ocean from the cul-de-sacbrbrOutdoor Living -br* Private backyardbr* Outdoor shower (a Cape Cod must!)br* Screened-in porch for breezy eveningsbr* Fire pit for family nights under the starsbr* Storage shed with beach gearbrbrAmenities Included -br* Fresh sheets, bath towels, and beach towelsbr* Pantry with spices and basicsbr* Limited paper goods & toiletries providedbr* Beach chairs & sand toys, Corn Holebr* 5 Bikes and Helmets availablebr* Game-filled cellar: ping pong table, air hockey, magnetic dart board, punching bag, two big wheels for toddlersbrbrFamily-Friendly Extras - br* 2 Pack-n-Plays (with sheets & blankets)br* 2 booster seatsbr* Door at the bottom of the upstairs for added privacybr* Every bedroom has a closet and dressers for most beds.brbrInside the Home - br* Bright, breezy kitchen, well-stockedbr* Open family & dining room areabr* Cozy fireplacebr* Screened porch directly off the living spacebrbrPrime Location -br* Walk to Skaket Beach (about 10 minutes).br* Close to town center, within a mile or so to restaurants, groceries, convenience stores, gift shops, ice cream, mini-golf, and morebr* Easy bike ride to town along the bike pathbr* about ½ mile to the Cape Cod Rail Trail (midpoint of 24-mile bike path)br* About 1 mile to Rock Harbor for deep-sea fishingbr* About 3 miles to Nauset Beach (ocean side)br* Close to the Cape Cod National Seashorebr* Home to a team in the Cape Cod Baseball Leaguebr* Easy access to whale watching, theaters, golf, galleries, cinemas, and more from Provincetown to HyannisbrbrCheck-in: 3:00 PMbrCheck-out: 10:00 AMbrbrFor the space, location, and amenities, this home is a true Cape Cod bargain. It's ideal for summer renters seeking comfort, convenience, and classic coastal charm!brbrHere are some of our favorite activities in or near Orleans:br* Chocolate Sparrow for breakfast, coffee, ice cream, and candy br* Nauset Beach band concerts on Mondaysbr* Walking the flats at Skaket Beachbr* Flax Pond in Nickerson State Park (Brewster)br* Cape Cod Bike Trailbr* Rock Harborbr* Orleans Firebirds baseball gamesbr* Orleans playgrounds (by elementary school) br* Town tennis and pickleball courtsbr* Nature trails at the National Seashore (Eastham & Wellfleet), Fort Hill (Eastham), and the MA Audubon Society (Wellfleet)br* The Land-Ho and Yardarm restaurants (Orleans)br* Plays at the Academy of Performing Arts (Orleans)br* Wellfleet Drive-Inbr* Sunsets at Skaket Beachbr* Walking around Provincetown.br* Brewster General Store for penny candy and gifts - put a quarter into the music machine!br* Getting a 10-visit gym pass at Nauset Fit Cobr* Movie, Pit, and Game Nights at Home

Bed

Bath

Sleeps

$589.42

/ Nightly

Private Vacation Home

Beach Road pearl

Orleans, Massachusetts, United States

Discover this hidden gem Classic Cape style house located in East Orleans and situated on a private 1.19-acre knoll.brThe spacebrThe primary second-floor bedroom has an ensuite bath along with two other generously sized bedrooms and a full bathroom on the first floor. A/C mini-splits perfect for warm summer nights or enjoy the screened in porch. Finished basement perfect for a visitor or play room. Short jaunt to area shops and restaurants. 1 Mile to Nauset Beach.brbr**Bring your own bed sheets (2 queen beds and 2 twin beds) pillow cases and bath towels.**brAs an option, on your way in there are several linen rental companies on the cape or Furies Linen Rentals out in Wellfleet.brbrThank you from the Martin Family.brGuest accessbrWhole house

Bed

Bath

Sleeps

$479.07

/ Nightly

Private Vacation Home

Rock Harbor Hideaway

Orleans, Massachusetts, United States

Immaculate and beautifully renovated three bedroom home just 1/2 mile to both Orleans Main Street and Rock Harbor. This sunny and bright home is set back from the road and offers privacy and the charm of Cape Cod. Main level with living room w/TV, dining room, fully equipped kitchen, two bedrooms (both with TVs) and one full bath. Upper level offers a spacious open room with twin beds and a hangout space with seating and large flat screen TV. Enjoy a day at the Rock Harbor Beach and the spectacular sunsets or head to Skaket Beach which is just 1 mile away. Central AC, Outdoor Shower, cooler, beach chairs, and beach toys. New patio!

Bed

Bath

Sleeps

$690.79

/ Nightly

Cottage

Peaceful Nauset Beach Sanctuary

Orleans, Massachusetts, United States

Imagine driving down a quiet private dirt road behind one of the nicest beaches on Cape Cod. Enter the property through a gate and walkway and you’re in your own private sanctuary. The cottage feels like a treehouse looking onto the tidal marsh behind Nauset Beach. Inside you will feel the vibes of a nostalgic cape cod cottage with modern amenities and style. Roll out the yoga mats! Chill out on the large deck overlooking the marsh and enjoy the birds. Take a 10 minute walk to your own private Nauset beach access. If walking is too much than pack the car and drive to a private free parking area that is only a short walk over the bridge to Nauset beach.brThis is a new listing in May of 2023. We are experienced VRBO hosts that have accumulated over 42 5 star reviews with our former rental. We love to host and take pride in giving our guests a great experience.

Bed

Bath

Sleeps

$292.91

/ Nightly

Private Vacation Home

Nauset Heights Cozy Cottage

Orleans, Massachusetts, United States

Close to Mill Pond, Pricilla's Landing and Only 3/10th's of a Mile to Nauset BeachbrbrCozy three-bedroom cottage in the desirable Nauset Heights area. brbrEnjoy the best that the Heights has to offer, being so close to Mill Pond, Pricilla's Landing and only 3/10th's of a mile to Association access stairs to Nauset Beach. brbrThis charming cottage has light knotty pine walls throughout and offers a kitchen with dining area, living room, three bedrooms; one on the north side of the house with a queen bed, and two separate bedrooms on the south side of the house with two twin beds in each. Ther is also a full bathroom with a bathtub.brbrAmenities include: a large air conditioner in the main room, wireless internet, ceiling fans in all bedrooms as well as the kitchen, five portable fans, flat screen television in the living room, enclosed outdoor shower, Weber charcoal grill and a dining table and umbrella on the deck. Sheets and towels are not provided. Please note that the deck awning has been removed.brbrBeds: Bedroom #1 - Queen, Bedroom #2 - Two Twins, Bedroom #3 - Two TwinsbrbrLocation: Priscilla's Beach on Mill Pond is 0.3 mile away. The private association beach stairs or Callanan's Pass to Nauset Beach is 0.4 mile away. The public Nauset Beach Parking Lot is 1.3 miles away. Orleans center and the bike trail access is approximately 3.5 miles away. And Skaket Beach on the bay side is 5.1 miles away.brbr* Additional fees: $175 Cleaning Fee, $220 non-refundable reservation fee; $30 damage protection fee; guest services fee; all applicable taxesbrbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* NO PETSbr* FREE WIFI br* OCCUPANCY: 6 PEOPLE TOTAL (adults and children)br* PARKING FOR 2 VEHICLESbr* SHEETS AND TOWELS ARE NOT INCLUDED, available to rent from local linen company, we are happy to provide informationbrbr****FREE ACTIVITIES INCLUDED****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area.brbrClick the Xplorie button or visit the Free Activities page to see the free fun included with this Kinlin Grover Compass rental!brbrAs a guest of Kinlin Grover Compass, you'll receive free golf tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities!

Bed

Bath

Sleeps

$765.97

/ Nightly

Private Vacation Home

Five Bedrooms Plus a Fully Equipped Game Room! (2085)

Orleans, Massachusetts, United States

Enjoy over-sized fun in this Orleans vacation rental! 5 bedrooms/3.5 baths tucked in close to Nickerson State Park hiking trails and delightful Bakers Pond. Ample bedding provides sleeping for up to 18 in this pet friendly contemporary home. Two private king bedrooms and one queen, plus a bedroom with two queens and a large shared room with six twins and another queen. There are comfortable seating areas throughout the house including living room, screened porch, finished basement, a backyard deck and picnic tables. In addition to backyard fun the basement has ping pong, Foosball, air hockey and games. Less than .5 mile to a public beach on Bakers Pond or hike into the park to Higgins Pond, both great for swimming or kayaking. Dogs on a leash are allowed in the park. Convenient to Orleans beaches, shopping and restaurants. Driveway parking for 4 cars. 3 night minimums available with an added cleaning fee. Save the cleaning fee by booking 7 or more consecutive days. Book today! An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

Bed

Bath

Sleeps

$796.62

/ Nightly

Private Vacation Home

Pochet Association - Nauset Beach Access - Central Air (2161)

Orleans, Massachusetts, United States

Situated in the desirable private Pochet Association area of East Orleans, this spacious four bedroom Cape Cod home makes for a perfect place for your whole group to stay! At the end of the short dirt road (1/10th a mile from the house) is a foot bridge for private access to coveted Nauset Outer Beach! The open and spacious interior allows for your family to spread out and relax after a day spent at the beach. This home is a great choice for a group who wants to be in a quintessential Cape Cod neighborhood. There are ductless AC in every room and a full well equipped kitchen with new appliances to prepare meals. The first floor has one bedroom with 2 twin beds and the other with a queen and full bath with a tub. Second floor features two more additional guest rooms (both with king beds) with full bath with a tub. Enjoy this peaceful setting with lovely gardens and beautiful outdoor patio. Play a yard game in the private yard-perfect for enjoying dinner or cocktails outside. The enclosed outdoor shower is available for those who prefer to rinse off outdoors under a star filled sky! An evening bbq, some yard games, board games, and many comfortable areas to sit and connecting with friends and family make this home an ideal choice for your next Cape Cod getaway! An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

4

Bed

2

Bath

10

Sleeps

Vacation Rentals By Owner In Orleans, MA

$775.35

$604.3

$632.05

$1035.77

$2231.46

$573.33

$532.76

$449.79

$1133.01

$397.4

$1661.35

$368.35

$722.47

$589.42

$479.07

$690.79

$292.91

$765.97

$796.62

Rent a place that suits your needs

Most popular vacation rentals in Orleans

$2351.25

$1705.31

$1716.10

$1728.77

$1872.34

$1989.18

$2231.46

$3799.10

$2966.17

$2753.95

Most Popular Cities in Massachusetts