Vacation Rentals By Owner In Orleans, MA

$385.11

15 min Walk to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15537 - Starry Night: 15 min Walk to Nauset Beach!brbrbrbrThe Space:brbrConveniently located between three bodies of water, our home in East Orleans is a water lovers dream! Each day choose between kayaking in Orleans Cove, swimming in Mill Pond, or surfing on the best waves of Cape Cod at Nauset beach--just a 15 minute walk from the home! br br After a fun filled day outside, come home and relax on the cozy sectional and watch TV or head out to the sun porch and catch a few more rays. Turn on the decorative lights and cook dinner on the grill out back, or walk just a few steps inside and prepare a meal in the fully stocked Kitchen. The Kitchen features Stainless Steel Bosch and G.E. appliances, microwave, toaster and coffee maker for quick mornings on the go! After dinner, rinse off in the outdoor or indoor shower before settling in for the night. Enjoy a family moment sitting in the Adirondack chairs around the fire pit outside, or curled up around the wood stove inside on those rainy nights. brbrOur home has three bedrooms and one full bathroom-- perfect for six adults or a family! The Master Bedroom is located at the end of the hall, on the right hand side. It has a King size bed and both a closet and bureau for storage. Across the hall is the second bedroom, with a Queen size bed, closet, and private entrance to the sunroom porch that runs along the back of the home. The last bedroom is on your left as you walk back to the main room, and has a Full size bed and bureau. Across from the final bedroom is the full bathroom, equipped with a shower and washer/dryer. All bedrooms have a Window A/C to keep you cool, even on the hottest days of summer!brbrOther amenities include WiFi, cable TV, gas grill, dog friendly, and sheets and bath towels provided for each guest. Last but not least, you’ll be conveniently located close to Nauset Farms, Whisk, or Cornerstore-- all great lunch options! Our summer home is the perfect place to soak up the summer and create warm memories that’ll stay with you all year round!brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 6br-1 FloorbrBedroomsbr-Total: 3br-1st Floor Bedroom Master Bedroom: 1 King Bed (converts to 2 Twin Beds)br-1st Floor Bedroom #2: 1 Queen Bedbr-1st Floor Bedroom #3: 1 Full BedbrBathrooms:br-Total: 1br-1st floor full bathroombrOther Amenitiesbr-Gas stove in living room is not for guest usebr-Window A/Cs in Bedroomsbr-Cable TVbr-Smart TVbr-WiFibr-Dartboardbr-Washer/Dryer br-Gas Grillbr-Stone Fire Pitbr-Sunporch with Furniturebr-Backyard with Furniturebr-Outdoor Showerbr-Please note outdoor amenities are available seasonallybr-There is parking for a maximum of 3 carsbr-Walk to Water-- 15 minutes to Nauset Beachbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0409382240brbrbrbrThe Neighborhood:brbrGeneral

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Sleeps

$1989.18

/ Nightly

Private Vacation Home

Piece of Paradise: 054-OL Magnificent Orleans Estate w/Pool, Tennis, Assoc. Beach on Pleasant Bay

Orleans, Massachusetts, United States

This property is professionally managed by Pretty Picky PropertiesbrbrMagnificent Orleans Estate w/Pool, Tennis, Assoc. Dock & Beach on Pleasant BaybrbrSleeps up to 14brLinens Included, Beds MadebrRents Friday to Friday in Peak SummerbrbrPool & Hot Tub open from Memorial Day to Columbus DaybrbrThis stunning South Orleans property is located within the Quanset Harbor Club, an upscale, private, seaside homeowners' association fronting on Quanset Pond, an inlet on the north shore of picturesque Pleasant Bay, at the southern-most end of the Cape Cod National Seashore. It's a short walk from the home to the private association beach and dock. Bring your boat or kayaks to explore Pleasant Bay and the Atlantic beyond. This residential neighborhood is also adjacent to a nature preserve with fresh and saltwater ponds, woodlands and secluded walking trails!brbrThe property is park-like itself, with 1.65 acres of tastefully landscaped lawns, gardens, beautiful hydrangeas, stonewalls and shade trees. It feels like your own private Cape Cod resort!brbrYour outdoor recreation options include the custom, heated saltwater pool and the regulation size tennis court, each with its own shaded patio and seating areas. There's a full-sized basketball hoop here as well and a fire pit! The oversized deck, shaded by a broad, retractable awning, invites you to dine alfresco overlooking the expansive grounds. The gas grill and enclosed outdoor shower are part of the outdoor living experience as well, along with the relaxing hot tub. The spacious grounds are large enough for the kids to have plenty of space to run around or host a soccer or whiffle ball game. The yard is also the perfect spot for family corn hole tournaments!brbrThe home's interior offers more than 5,500 square feet of luxury living in every detail. It recently underwent a stem to stern first class renovation, and is just immaculate with tasteful décor, elegant finishes and all new kitchen and baths.brbrAn open floor plan allows for seamless entertaining with two living areas, a chef's kitchen, and a vaulted ceiling sunroom with massive windows which flows out to an expansive open deck overlooking the pool and tennis court. There is also a lounge with a writing desk that can serve as an office or quiet retreat by day and host cocktail hour in the evenings.brbrThe superb custom chef's kitchen provides every imaginable element to make meal prep a fun time for all involved, including a large island with seating for four.brbrThe main level is home to the spacious primary bedroom with its big king size bed and en suite full bath, including an attractive tile and glass step-in shower, separate tub and double sink vanity. This level of the house also contains a half bath and the laundry/pantry.brbrUpstairs in the main house you'll find two bedrooms. One is the second primary bedroom with a comfy king size bed, upholstered reading chair and gorgeous views of the grounds. The other bedroom is perfect for the kids with a set of bunk beds plus another twin bed with a trundle. This room also has a “secret” kids only area with a TV and PlayStation console. These two rooms share a private Jack & Jill style full bath with a tub/shower combo and another, large two-sink vanity.brbrThe finished lower level provides an oversized play room/TV lounge, with a large screen smart TV, XBOX console, Pop-a-shot basketball game and a full size Golden Tee arcade game! There is also another guest bedroom with two queen beds, a full bath with tile shower and a work out room with professional equipment. This level walks out to a covered bluestone patio with comfortable lounge seating, the new 45 jet six-person hot tub, and is a short walk down to the fenced-in pool area.brbrA separate stairway leads up into the suite over the garage, where you'll find a private third primary bedroom with a king size bed and full bath with glass enclosed tile shower. This expansive space also has a large living area that can double as another sleeping area with a full size day bed with trundle as well as a twin day bed with trundle. The perfect spot for a family to set up camp.brbrNaturally, the home offers high speed Wi-Fi, smart TV's, and central air conditioning.brbrThe home's location is also ideal for exploring the Lower Cape. If you can ever convince your group to leave, it's just a few miles drive to downtown Chatham, Chatham Bars Inn, downtown Orleans, Nauset Beach and so many fabulous restaurants and shops.brbrThis property is a rare combination indeed -- upscale home, pool, tennis, dock, and beach. It's a sublime mix of fun and relaxation for your group in an idyllic setting. Bring the whole family to enjoy this private piece of paradise on the Cape!brbrPlease enter 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 rental terms less than 31 days that total 17.45%.brbrBe sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod.Cod.brbrIt's your vacation. Get Picky! ®

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Sleeps

$438.72

/ Nightly

Private Vacation Home

Rock Harbor Retreat: Special Get-Aways available in Sept. Week/Wk-ends available

Orleans, Massachusetts, United States

Architecturally designed and built in 1989, this relaxed well-appointed vacation home is a perfect vacation get-away! Details include--brOpen Floor Plan -- Quiet - Private - Sunny - Immaculate - Relaxing - Bright - brNew Kitchen flows into Dining Room which flows into the Living Room --through French doors onto a screened porch!br10 foot high beamed ceilings downstairs - Cathedral ceilings upstairs --br-With very high ceilings, large windows and French doors, we have excellent cross ventilation and air-circulation!br- French doors from the living room open to a shaded screened porch --br-Additional French doors from the master BR lead to a private tree top level wrap around deck with umbrella and comfortable wrought iron patio furniture -br-Beautiful NEW custom tiled shower with glass doors downstairs and luxurious 7 foot tiled shower upstairs!!brVery comfortably furnished with many extras - Beautiful NEW well equipped kitchen!! New Cabinets, Tile, Quartz Countertops, Stainless Appliances and Dishwasher --brComfortable couch and living room furniture.brSmart HD TV with enhanced Cable - Wireless Internet connection-- Blue Ray DVD Player - Stereo - Microwave - Coffee Maker - Toaster - Fans - New W/D - Gas Grill - brPorch and outdoor furniture -- brColorful perennial gardens to enjoy! brbrPlease be aware that we provide comfortable beds for our guests with quilts, blankets and pillows. We are unable, however, to provide sheets and towels, but can provide a listing of local companies that rent out linens.brbrClose to everything!!: Walking distance to casual and fine dining, coffee houses (the Hot Chocolate Sparrow is a 5 minute walk), galleries, shops, the Cape Cod Bike Trail (.2 miles), and Rock Harbor (.7 miles). Short drive to Skaket Beach (1 mile to the bayside beach) and Nauset Beach (3 miles to the National Seashore - on the ocean side). The Nauset Beach, part of the Cape Cod National Seashore, was voted one of the most beautiful beaches in America.brbrMany things to do!!: The National Seashore Center in Eastham offers many programs for families, as well as the Audubon Center in Wellfleet. Several Summer Playhouses offer theater which changes on a weekly basis, such as the Academy Playhouse in Orleans, the Dennis Playhouse, the Wellfleet Harbor Actor's Theatre (WHAT). There is a Farmer's Market on Saturday morning in Orleans (a short walk from the house and next to the Hot Chocolate Sparrow), and frequent Art Shows. There are weekly summer band concerts at Nauset Beach, and surrounding towns, and for the kids (big and small) there is mini- golf located nearby. For sports fans, the Orleans Fire Birds, a Summer Cape League Baseball Team, plays regular games about one mile away. Rock Harbor offers deep sea fishing adventures and there is surf fishing at Nauset Beach. Whale watching is a popular activity leaving for Stellwagen Banks from Provincetown. And, finally, the Cape is a bird watcher's paradise!brbrPlease be aware that weather/storm refunds are not offered. Please arrange for vacation insurance for storm protection, if desired. brbrDuring the high summer months of July and August, please make your reservations for one or two weeks at a time, Saturday to Saturday. During June or September, longer or shorter periods of time are welcome.

3

Bed

2

Bath

6

Sleeps

$294.3

/ Nightly

Cottage

Cozy 1 bedroom cottage in beautiful Orleans with AC. A perfect spot to get away.

Orleans, Massachusetts, United States

Your getaway awaits in Orleans at this pleasant cottage. Guests will find one bedroom with a queen bed, a fully equipped/modern kitchen, plenty of outdoor space and seating plus an outdoor shower. The excellent living room includes a comfortable couch/sofa bed, perfect for extra guests or relaxing evenings. With heating and air conditioning, the space stays comfortable no matter the season. Whether you’re unwinding after a day at the beach or enjoying quiet moments inside, this wonderful cottage offers a welcoming retreat. Plenty to see and do in area towns from Chatham to P-Town, as our location is just a car ride away for an excellent day trip. Great local beaches and dining locations to choose from. Book now and enjoy everything this cottage has to offer.

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Sleeps

$925.14

/ Nightly

Private Vacation Home

Private Beach - 3 bedroom

Orleans, Massachusetts, United States

Welcome to The Lookout on Pleasant Bay.brbrThis remarkable property has a Deed to a private beach. brbrThe main home sleeps up to 8. See below for information on extra sleeping space available at an extra cost. Central air conditioning is provided in the main dwelling. The entire home has been newly renovated in a coastal farmhouse motif and includes all new state-of-the-art appliances, furnishings and decorations. Overall, the look of the property was designed to bring back the Ye Olde Cape Cod feel but not at the expense of creature comforts such as air conditioning and Smart TV technology. This rental is ideal for small families, multi-generations, large families or even multiple families and provide for an all-inclusive vacation experience. brbrSituated on 2 1/2 acres, this vacation home provides large open-concept common spaces both inside and out. Several amenities have been included and are readily available for use. These extra amenities will undoubtedly fulfill the perfect Cape Cod vacation experience. With the access to a private beach, this vacation rental includes brand new kayaks, paddle boards and life vests at no extra cost. Wireless internet access is provided throughout the home with new large screen TV’s in the living room, and main floor master bedroom. All beach, bed and bath linens included, as well as the cleaning fee. brbrEnjoy the fabulous water views from the comfortable AC living room with multiple bay windows or from the enclosed glass sunroom. If fresh air is your choice, hang out on the flagstone deck covered with a brand new pergola with comfortable seating while the children play football/volleyball/soccer games out on the sprawling rolling lawn. Or, if the sandy beach is your jam, bring the provided Tommy Bahama chairs, cooler and umbrella and take a swim, watch the boating activity on Pleasant Bay or hop on one of the kayaks or paddle boards and take a spin in the calm waters of the bay. brbrFor dining, there are many seating options. The inside farmhouse table extends and seats up to 12. Two other tables are also available. In the sunroom and outdoor patio seating allow for up to 8 additional guests each. Enjoy the spectacular sunsets from the lounge chairs on the deck or the Adirondack chairs on the lawn. A large new BBQ with side burners is also provided. At night under the stars, sit around the fire pit roasting marshmallows and making s’mores. brbrThe main house boasts 3 bedrooms, 3 full bathrooms (two with shower/tub combos). Additionally, there is a large outdoor shower which also includes a changing area. Of the three main house bedrooms, two are suites with king size beds. The main floor king bed master has an en-suite whereas the upstairs king master bedroom shares a Jack and Jill bathroom with the third bedroom. The third bedroom has two full size beds. brbrThe property is available by the week from June through September and by the night (with a 3-night minimum) in the off season.brbrThis listing is for 3 bedrooms and 3 baths. However, there is extra sleeping space available in a separate building we call the bunkroom/game room. This space has 3 bunkbeds sleeping 6 extra guests. The bunkroom is attached to the house but can only be accessed from outside. This space is available for an extra fee during the summer season. Inquire within for details.brbrPlease note: So sorry, we do not allow events or bachelor/bachelorette bookings or large party groups. No more than 4 cars are allowed in the driveway.

3

Bed

3

Bath

12

Sleeps

$462.43

/ Nightly

Private Vacation Home

Short Walk to Water, Mins to Nauset Beach, AC!

Orleans, Massachusetts, United States

Summary:brbr15596 - Sandy Wishes: Short Walk to Water, Mins to Nauset Beach, AC!brbrbrbrThe Space:brbrWelcome to Sandy Wishes, your dreamy Cape Cod escape in beautiful Orleans. With sweeping water views of Town Cove and just a short stroll to the nearest landing, this newly renovated retreat offers the perfect balance of tranquil seclusion and fun-filled moments, ideal for up to 6 guests.brbrImagine starting your day with a morning coffee on the second-floor deck, overlooking the serene cove as the sun sparkles on the water. The spacious backyard invites you to relax and gather, complete with a grill and outdoor seating for cookouts under the Cape Cod breeze, while kids and adults enjoy lawn games and open space.brbrInside, the home features a fresh, modern style with bright, airy living spaces and a fully equipped kitchen that makes it easy to cook and connect. Designed with comfort in mind, Sandy Wishes comfortably sleeps six guests across three inviting bedrooms, including a king and queen on the first floor and a versatile queen Murphy bed upstairs. Two full bathrooms, one on each floor, provide convenience and privacy, while central air and a washer/dryer ensure a comfortable and easy stay.brbrAfter a day of exploring, unwind back at your Orleans oasis with a ping pong match, relax with a movie on the smart TV, or gather around the outdoor firepit with your favorite cocktail as the evening settles in.brbrWhen you’re ready to head out, the location couldn’t be better. Just 0.4 miles from your door, you can access the landing to launch rented kayaks or SUPs on Town Cove, while Nauset Beach is only an 8-minute drive away for toes-in-the-sand. Downtown Orleans is just minutes away, offering boutique shopping, dining, and even a chance to catch a Cape Cod Baseball League game.brbrOn your way to the beach, stop at Nauset Farms for fresh-made subs, gourmet snacks, and all your beach-day essentials. When it’s time to dine out, enjoy local favorites like The Barley Neck, known for its laid-back outdoor vibe; Cooke’s Seafood for fresh seafood staples like lobster rolls and fried clams; Sunbird Kitchen for a bright, farm-to-table breakfast or coffee to start your day; and Ice Cream Café for a well-earned scoop after the beach. For a fun indoor outing, The Alley offers classic candlepin bowling paired with great BBQ—perfect for a laid-back night or a rainy day activity.brbrSlow down, breathe in the salty air, and create unforgettable memories at Sandy Wishes—your perfect Cape Cod getaway. Book your stay now—your coastal story begins here!brbrHome Details:br-No Pets(Fines Remitted)br-Sleeps 6brBedroomsbr-Total 3br-1st Floor Bedroom: 1 King Bedbr-1st Floor Bedroom: 1 Queen Bedbr-2nd Floor Bedroom: 1 Queen (Murphy Bed)brBathroomsbr-Total 2br-1st Floor: Full Bathroom, with Showerbr-2nd Floor: Full Bathroom, with ShowerbrOther Amenities br-Central A/C br-WiFibr-Smart TV br-Streaming Service br-Game Roombr-Ping Pong Tablebr-Washer/Dryer br-Propane Grillbr-Wood Fire pitbr-Outdoor Games (Yard Games)br-Please note outdoor amenities are available seasonallybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 2 cars maximumbr-C0580052240

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Sleeps

$535.56

/ Nightly

Private Vacation Home

Central AC, Spacious, 5-level, beautiful home, near lakes and beach

Orleans, Massachusetts, United States

Central Air- conditioned - 4 Bedroom, 5 level home in Orleans, Cape Cod. Within walking distance Crystal Lake offers fresh water swimming, fishing and lazy days of floating on your raft. In less than two miles, you can be at the nationally renowned Nauset Beach to spend a day surfing, fishing or even 4 wheeling on the miles of the outer beach. The Orleans Skaket bay beach offers more tranquil water for small children to spend the day seeking sea creatures and building sandcastles. For the golf lover, the amazing Captains Public Golf Course is within two miles of the front door. brThe layout of this roomy, 3,000 square foot home suits a large family or two families who want both shared and separate living space. The open floor plan of cathedral roomed kitchen and dining areas which overlook the enormous living room area lends itself to large vacation gatherings. In addition, a second family room offers a getaway space for children and teens who may need their own space.

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$945.13

/ Nightly

Private Vacation Home

Spacious Home Ideally Located a 5 Minute Drive from Nauset Beach

Orleans, Massachusetts, United States

Summary:brbrAmazing location close to popular restaurants & beaches. 2 Miles from Nauset Beach and 6 miles to Skaket Beach Shared access to nearby Meetinghouse Pond!brbrbrbrThe Space:brbrThis home is represented by Nauset Rental, a local vacation rental management company.brbrbrbrWelcome to High Tide Haven, an impressive home found in a peaceful neighborhood in East Orleans. This 3-bedroom, 3-bathroom home is open and spacious, awash with natural light. With nearly 2200 square feet of space, groups of up to ten can gather here comfortably. The home is located within walking distance from several popular restaurants, like The Rail, or The Barley Neck Inn. Shared access on the waterfront at nearby Meetinghouse Pond offers a great opportunity to bring your kayak and explore the quiet inlet. brbrbrbrUpon entering High Tide Haven, you are met with a large living room with vaulted ceilings. The space continues with an open-concept style up a couple of steps to a welcoming dining area off the kitchen. The property has a magnificent kitchen with multiple skylights overhead that bathe the space in light. On a rainy day, you can enjoy solving jigsaw puzzles in the cozy living room, and bird lovers will appreciate having a pair of binoculars and a telescope during migration season. The spacious and sunny deck can be accessed from both the kitchen and the living space. It has plenty of outdoor furniture for lounging, including two outdoor love seats and a coffee table, and you can enjoy playing cornhole after dinner. There is also a new teak dining table with an umbrella that extends for additional seating, a gas grill for barbecuing on summer nights, and an outdoor shower to rinse off after a day at the beach. For dog lovers, there is a fully fenced-in backyard, so your four-legged friend can run around outside worry-free. brbrbrbrHigh Tide Haven is a spectacular home base for your Cape Cod adventure. The proximity to the Atlantic Ocean, downtown shops, and restaurants is unbeatable. High Tide Haven is within walking distance to Nauset Farms Market, and Smitty's Ice Cream. A short drive up Route 6 brings you to the famous Cape Cod National Seashore, where you can enjoy the unrivaled natural beauty of Cape Cod with miles of woodland trails, bike trails, and sweeping ocean views. Come here to relax with friends and family in the salty ocean air! brbrbrbrLayout of Bedrooms & Bathrooms: brbrbrbrMain Level:brbrBedroom #1 - King ensuite w/vaulted ceilingbrbrBedroom #2 - KingbrbrBedroom #3 - 1 Queen and 1 Twin - slider to small deckbrbrPrimary Bath stand-up shower, double vanitybrbrHall Bath Full with tub/ShowerbrbrbrbrLower Level:brbrBonus Room - Twin trundle bed and a queen bed brbr3/4 Bathbrbrbrbr***We welcome approved low-impact DOGS - TENANT must reach out to Nauset Rental with dog details for approval either before making reservation or within 48 hours of submitting online reservation. We will need to know the following information:brbrbrbr*Any shedding brbr*Any issues with accidents - urination or throwing up brbr*Any issues with chewing furnishings brbr*Barking while unattended or while attended brbr*Does your dog receive flea and tick preventative brbr*Are you confident you can leave property with no sign of your dog when you check out brbrbrbr**Linens are included**brbrbrbrOther Things to Note:brbr-

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Sleeps

$541.19

/ Nightly

Private Vacation Home

Comfortable, Cozy & Spacious Orleans Cottage on Quiet Road & Close to Everything

Orleans, Massachusetts, United States

After a week in this house, you will never want to go back to reality - but at least when you go back you will be refreshed and come away with incredible memories! This spacious Cape Cod cottage is located on a quiet street in a lovely neighborhood in Orleans, Massachusetts, less than 5 minutes away from every possible activity you could ask for - the beach, the bay, ponds, restaurants, shopping and so much more! This 5 bedroom home can comfortably accommodate 12 people and is completely equipped for a summer vacation, with beach chairs, boogie boards, toys, umbrellas, as well as all the amenities of a home for cooking meals, bbqing, lobster bakes and entertaining inside and out. One of the best features of the house is the outdoor areas - you are guaranteed to enjoy the beautiful yard and inviting back deck. There is a screened in porch, as well as a newly added shaded seating area in the backyard. brbrThe location absolutely can't be beat, it sits on a quiet and quaint road, but is so close to everything. It's a 5 minute drive to one of the best beaches in the country, Nauset Beach, and it's just a 5 minute drive to Cape Cod bay with it's own beaches and harbor. It's an easy 5 minute walk or bike ride to a small boat landing looking out to Orleans Town Cove. This area is really fun for looking for shells and letting children explore. The house has an open floor plan with a large family room adjacent to the kitchen and a front sitting room. There is a master bedroom on the first floor with a king bed and it's own bathroom. There is another bedroom on the first floor with an adjacent bathroom. Upstairs, there are 3 bedrooms and 1 bathroom. Upstairs: One bedroom has a queen bed, another bedroom has a queen bed, and the third bedroom has a trundle bed & a twin (sleeps 3 kids). The upstairs is perfect for small children! And don't forget to enjoy the outdoor shower - you can't have a true Cape vacation without it. The outside of the house is just as comfortable as the inside - with 2 seating areas and a large yard in the front and back. And this home is a gardener's dream - with over 25 rose and hydrangea bushes, you will feel like you're in heaven. brbrRentals are Friday to Friday.

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Sleeps

$1670.97

/ Nightly

Private Vacation Home

5 Min Walk to Nauset Beach, Saltwater Heated Pool & Hot Tub

Orleans, Massachusetts, United States

*Booking now for spring and summer 2026 - fully books every summer so book now! * brIn-Ground Saltwater Heated Pool & Hot Tub with automatic pool cover open May through October! Large home just a short walk via a private path to Nauset Beach. Three large bedrooms include their own bathroom, while the fourth bedroom is a private room in the newly finished (for 2022) lower level adjacent to a new full bathroom. Enjoy two spacious primary bedroom suites, one on each floor, both with king-size beds. The first floor primary bedroom includes a large walk-in closet, new hardwood floors (2024) and renovated bathroom with new walk-in shower (2024). The third bedroom, which includes a peek of the ocean, consists of two huge rooms (18 x 14 and 15 x 13) with two sets of twin beds. The fourth bedroom is a private room in the newly finished (2022) lower level adjacent to the new game room with walk-out access to the pool. Enjoy ping pong in the basement or watch the 65 tv! There is a new pull out couch in the basement game room that sleeps 2 (only sleeping room not private) allowing for a total of 12 guests. The main level open floor plan includes both gas and wood burning fireplaces. The updated kitchen offers natural gas for cooking, granite counter tops, a built-in microwave, and an island. Kitchen is well stocked with every cooking tool or utensil you will need - ideal for guests who like to cook. The kitchen leads into a large living room with plenty of space to unwind. Double French doors open from the living room onto a 24 x 15 foot elevated outdoor deck with a gas grill and large outdoor dining table - great for outdoor meals, entertaining, sunning, and R&R. The deck overlooks a forest of trees and foliage that provide privacy for this .80 acre lot. Through the trees you can catch another peek of the ocean to remind you that Nauset Beach is a stroll away. The home includes central A/C (with two zones), an outdoor shower, 1st floor washer/dryer, central vacuum, and a one car garage. Note towels and linens are not provided, but owner can email info with contact information of local providers.

5

Bed

4

Bath

12

Sleeps

$536.1

/ Nightly

Private Vacation Home

Nauset Heights Carriage House

Orleans, Massachusetts, United States

Discover the serene charm of the Nauset Heights Carriage House, perfectly nestled in the picturesque Orleans area. This delightful one-bedroom retreat offers stunning water views and is just a short stroll down the ocean view path to a private association beach, making it an ideal getaway for couples seeking tranquility and connection with nature.brbrThe Carriage House features a cozy yet spacious layout, designed with comfort in mind. With one well-appointed bedroom and a full bathroom, it comfortably accommodates up to two guests, making it perfect for a romantic escape or a peaceful solo retreat. Enjoy the refreshing coastal breeze while lounging on your private deck, or whip up a delicious meal in the well-stocked kitchen, equipped with all the essentials for your culinary adventures.brbrInside, the ambiance is bright and inviting, thanks to central air conditioning ensuring your comfort during warmer days. After a day of beachside fun, unwind in the comfortable living area, where relaxation awaits. brbrWhether you choose to explore the beauty of Nauset Heights or indulge in the local attractions, such as charming shops, exquisite dining options, and scenic nature trails, you'll find plenty to do just a short drive away.brbrDon't miss out on this gem by the shore—book your stay at the Nauset Heights Carriage House and immerse yourself in the serene beauty of Cape Cod!

1

Bed

1

Bath

2

Sleeps

$1087.15

/ Nightly

Private Vacation Home

Elegant Coastal Retreat with Ocean Views Near Mill Pond

Orleans, Massachusetts, United States

Welcome to your perfect Cape Cod escape. This beautifully appointed four bedroom, two and a half bath coastal home offers the ideal blend of luxury, comfort, and location.brbrPerched to capture lovely ocean views and just moments from Mill Pond, the home is designed for easy summer living. The light-filled interior features a spacious open layout, warm wood floors, and a luxury kitchen that makes gathering effortless.brbrStep outside to multiple decks overlooking the water where morning coffee and sunset cocktails become part of the daily rhythm. The private yard and classic Cape architecture create a peaceful retreat while still keeping you close to Orleans beaches, dining, and village charm.brbrWhether you are planning a multi-generational vacation or a relaxed coastal getaway with friends, this home delivers space, style, and that unmistakable Cape Cod breeze. brbrMA Rental Certificate C0566652240

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Sleeps

$2397.73

/ Nightly

Private Vacation Home

Waterfront. Private beach. Pool. Estate has it all!!

Orleans, Massachusetts, United States

Chosen by Cape Cod Life magazine as one of the Top Ten places to stay on Cape Cod. Our waterfront estate now has a gorgeous heated pool plus breathtaking views of over 180 ' plus of Pleasant Bay and 300' of your own PRIVATE waterfront. Plus you are directly on the water, not across the street or down the lane. This very special property is a landmark to the area and owned by the same family since it was built on the shores of Pleasant Bay 100 years ago. It had been lovingly cared for and maintained and matches the grandeur of times past with modern amenities. It is an ideal environment for multi generational family members to vacation together - or old or new friends with lots of room to spread out, enjoy each others company, yet find privacy and peace.brbrDown the end of an old cape cod road, then down the end of a private seashell driveway, there are no streets, traffic, or even pedestrians nearby. Pleasant Bay is reached by a pathway down the bluff in front of the house. Although the sandy beach disappears during a high tide, there is a deck to sit on until the beach reappears. The Bay has a gradual sandy bottom, warm water great for swimming, floating on rafts, paddle boarding, sailing, kayaking, and walking along the shore. The new heated pool and deck area are sun filled and full of fun for all ages. There is a gas barbecue grill, seating for your family group, lounge chairs - everything you need for fun. The pool is open and heated from mid June until Labor Day. brbrThere are 3 acres of open lawn, 17 rms, 9 bedrms, 5 1/2 baths plus an enclosed outdoor showe. All of the bedrooms plus the dining room and family room are air conditioned. The kitchen features a 48' refrigerator, Corian counters, plus the estate includes a 2nd fully equipped kitchen. There is lots of room for everyone to spread out with three living rooms, game room with pool table, private deck on the beach and the pool and pool terrace. .The pool is 16.5' by 39'. br. brThe nine bedrooms are really nine bedrooms - not common rooms that become bedrooms at night with pull out sofas. There are no sofa beds, futons, trundle beds, bunk beds or cots. Everyone has a personal and private space. All of the bedrooms have twin beds or queens. The master bedroom has a king bed. Each bedroom sleeps two guests except for one extra large bedroom that has three twin beds. The 2 lofts have privacy walls and doors are accessed by staircases - on the west end thru the triple bedrm and on the east end thru the primary bedrm.brBeach, bed and bath linens are included for weekly rentals. Weekenders please plan to bring your own or use one of the local linen services. The cleaning fee is included for weekly rentals. Available by the week only from early June to late Sept. Please do not ask us about one or two night stays. The minimum is three nights and only occasionally in May or October. See a floor plan at our web site winslowestates.com. brbrSummer rentals are Friday to Friday so you can avoid all the headaches of the more typical Saturday with hours of backed up traffic. Great to include family and friends who otherwise could not enjoy a weekend with you.br brCancellation Policy - all payments returned upon ability to re-rent the same time period for the same amount.

Bed

Bath

Sleeps

$1705.31

/ Nightly

Private Vacation Home

Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Orleans, Massachusetts, United States

This warm and inviting 7 bedroom, 4 bath home sprawls over 4 stories of comfortable rooms with spacious, open living areas and a private, fully fenced back yard. Perfectly located in South Orleans, the house is just minutes from the Lower Cape villages of Chatham, Brewster and Orleans. A beautiful beach on scenic Pleasant Bay is just down the street.brbrA unique sixty foot oblong swimming pool dominates the back yard and is completely private. The front, side and back yards unfold over an acre, abundant with gardens and filled with flowers to enjoy.brbrThe kitchen features a large island with granite counters, a Viking stovetop, high-end stainless appliances and a Country French farm table which comfortably seats a large group. brbrA huge outdoor mahogany deck adjoins a 5-person cedar sauna and a cleverly designed mahogany barrel-style outdoor shower. A large hot tub completes the resort-like amenities. A Weber Genesis gas BBQ grill and an outdoor fire pit plus a generous assortment of plush lounge chairs and multiple umbrellas make 'hanging out by the pool' an experience equal to that of any five star hotel. (Note: The large hot tub is available off-season.)brbrTwo of the seven bedrooms are en suite, another is very large and features a comfortable sitting area with TV. The four bathrooms all have showers, and two of the bathrooms additionally have tubs, one with jacuzzi (see full descriptions below).brbrThe rumpus room / bedroom down cellar sleeps 6 in two double beds and two single bunks. Here kids (and adults) have a special place to hang-out with a smart TV and a small stage for putting on shows!

Bed

Bath

Sleeps

$634.3

/ Nightly

Private Vacation Home

Ideal Rental in Orleans Sleeps up to 10

Orleans, Massachusetts, United States

Ideal Rental in East Orleans Sleeps Up To 10brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrThis is an amazing vacation rental with so many wonderful amenities. Arrive to a beautifully landscaped property with lush plantings and a spectacular array of flowers. brbrEnter this delightful home with its cheerful and tasteful decor and you will find a spacious, well equipped kitchen, dining area, living room, wonderful family room, master bedroom including a king bed and with ensuite bathroom, and an additional half bath and laundry room, all on the first floor. brbrThe second floor offers three spacious bedrooms: one with a queen bed, one with two twins and a full size sleep sofa and a bonus room (bedroom #4) off the second bedroom with one queen bed, one full bed and one twin bed. brbrThe house sits on a large level lot with a deck, enclosed outdoor shower and an inviting fire pit on the roomy patio. brbrThis home is just 2/10's of a mile from the Meetinghouse Pond landing and just over 2 miles away from Nauset Beach and the center of Orleans. You'll be so close to East Orleans shops and restaurants. brbrBedroom #1 - King, Bedroom #2 - Queen, Bedroom #3 - Two Twins, Bedroom #4 - One Queen, One Full (Double), and One TwinbrbrAmenities include central air conditioning, wireless internet, five televisions, one with cable and the rest are Smart TV's with streaming, DVD player, dishwasher, washer and dryer, gas range, Keurig, air fryer, printer/scanner/copier, outdoor furniture, gas grill, 10 beach chairs, a ping pong table and pool table, air hockey table, corn hole set, and Kayaks. Linens are not included. brbr* Additional Fees:br- $250 Cleaning Fee, $220 Non-Refundable Reservation Fee; $30 Damage Protection Fee; Guest Services Fee; All Applicable Taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* 3-NIGHT MINIMUM STAY OFF SEASON ONLYbr* NO SMOKINGbr* OCCUPANCY: 10 (adults and children)br* PARKING FOR 4 VEHICLESbr* Sheets and towels not included, available to rent from local linen company, we are happy to provide informationbr***SATURDAY TO SATURDAY***NO SMOKING *** NO PETS***brbr**** 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 ODOHE

Bed

Bath

Sleeps

$751.56

/ Nightly

Private Vacation Home

Your perch to the Cape's best ocean view with private Nauset access for 8!

Orleans, Massachusetts, United States

Your private and peaceful post and beam home looks out from every room, including a screened dining porch and an eye-poping roof-top deck, across the tidal river and marsh of Pleasant Bay to the dunes and rhythmic waves of Nauset Beach. Watch the colors change from sunrise to sunset, see the birds, seals and teaming wildlife, wander down to the private foot bridge to the beach, or entertain your palate in your spacious, open kitchen, dining, and living space. This comfortable charmer is on Pochet Inlet in the Pochet Association just minutes from East Orleans, Nauset Farms, and dining options to match every taste. This tastefully expanded 4 bedroom, 2.5 bath home features a luxurious bath, indoor and outdoor showers, a multi-purpose loft for TV, extra sleeping space, or star gazing off the deck before returning to a roaring central fireplace. Choose from 3 main floor bedrooms (1 king, 1 queen, 2 twins) and 2 baths. The main room loft has 1 bedroom with 2 twins and 1/2 bath accessed by a one-of-a-kind spiral stairway. No pets please. Invite your friends instead to enjoy this truly special home.

Bed

Bath

Sleeps

$363.79

/ Nightly

Cottage

Fantastic Orleans Waterfront 2BR Cottage

Orleans, Massachusetts, United States

ENHANCED CLEANING/DISINFECTING and SELF CHECK-IN !brbrOn the picturesque town cove in Orleans Village. Right out your window you'll see the oyster farm, lobster men and shell-fishermen working. Enjoy the swans, ducks, herons, seals, horseshoe crabs... so close you can touch. Walk to town center, shops, restaurants,... kayak, sail, bike, fish, picnic, shell, grille, relax on the swings.... adjacent to historic Windmill Park and famous 'Goose Hummock' (kayak center and all-around outdoor activity hub). Our Nauset salt air is therapeutic and invigorating

2

Bed

1

Bath

5

Sleeps

$755.17

/ Nightly

Private Vacation Home

Waterfront Oasis with Game Space, Newly Renovated!

Orleans, Massachusetts, United States

Summary:brbr15594 - Coast Away: Waterfront Oasis with Game Space, Newly Renovated!brbrbrbrThe Space:brbrLet yourself be transported to effortless seaside living at Coast Away, a dog-friendly four-bedroom, two-bath waterfront oasis situated above Woods Cove in Orleans, complete with its own private beach just steps from the backyard. Here, 180-degree panoramic water views steal the show, especially from the expansive wrap-around deck where sunrise coffees and sunset laughter unfold to the soundtrack of the sea waves.brbrbrbrThis coastal retreat comfortably accommodates up to eight guests, offering a plush queen bedroom on the first floor and, on the ground level, three additional queen bedrooms. With one full bathroom on each floor, convenience and comfort are built into your stay. The newly renovated and fully equipped kitchen, designed with the home chef in mind, invites you to prepare your favorite seafood dishes and gourmet creations. When the day winds down, gather for streaming movies on the Smart TV or head to the game space for some friendly competition around the foosball table—perfect entertainment no matter the weather. Central A/C and heat, washer and dryer, and an outdoor shower ensure every modern comfort of a perfect beach house escape.brbrbrbrA private path leads you down to your own stretch of beach, where you can dip your toes in the calm waves, launch your kayak, or rent a paddleboard and explore the peaceful cove. Sunbathe, read, or simply let the rhythm of the tide set the pace for your day. It's easy to enjoy a nice meal cooked on the grill, eaten alfresco on the expansive deck at Coast Away, tailored to your every vacation need. The private yard offers plenty of space for kids and pets to play freely while you unwind by the fire pit. As night falls, sip your favorite drink beneath a starlit sky, feel the soft coastal breeze that Orleans is known for, and watch twilight settle gently over the water.brbrbrbrBeyond your retreat, you’re just a short drive from iconic beaches like Nauset Beach and Skaket Beach, celebrated for their spectacular sunrises and sunsets. On your way, stop at Nauset Farms for a fresh, delicious sandwich. Catch a summer game from the Cape Cod Baseball League at Eldredge Park. When it’s time to gather around the table, your favorite eateries await. Craving classic New England fare The Barley Neck Inn has you covered. In the mood for Italian-inspired dishes La Bella Vita Kitchen & Bar is the place to be. For live music and craft brews, Hog Island Beer Co. delivers the perfect evening vibe. Orleans downtown is just minutes away, offering charming boutiques and souvenir shops to complete your Cape Cod experience.brbrbrbrLet the waves, the breeze, and the view be your daily companions. Seize this rare waterfront gem, where every moment brings the ocean to your doorstep. Make your Cape Cod dream a reality at Coast Away.brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 8brbrBedroomsbrbr-Total 4brbr-1st Floor Bedroom: 1 Queen Bedbrbr-Ground Floor: 1 Queen Bedbrbr-Ground Floor: Queen Bedbrbr-Ground Floor: Queen BedbrbrBathroomsbrbr-Total 2brbr-1st Floor: Full Bathroom w/ ShowerbrbrGround Floor: Full Bathroom w/ Shower/Tub CombobrbrOther Amenitiesbrbr-Central via Split Systembrbr-WiFibrbr-Smart TVbrbr-Streaming Service brbr-Washer/Dryerbrbr-Indoor Fireplaces are not for guest use(fines remitted)brbr-Game Spacebrbr-Foosball Tablebrbr-Ping Pong Tablebrbr-Natural Gas Grillbrbr-Gas Fire Pitbrbr-Outdoor Shower brbr -Please note outdoor amenities are available seasonallybrbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbrbr-Cleaned with Hospital Grade Disinfectantbrbr-Parking for 3 cars maximumbrbr-C0572832240

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Bath

Sleeps

$784.8

/ Nightly

Private Vacation Home

Family Vacation Dream! Firepit, Outdoor Kitchen & Central AC

Orleans, Massachusetts, United States

An immaculate 3 bedroom, 3 full bath home on a beautiful private acre in Orleans, this home is perfect for families and is a great vacation property. brbrThe first floor has a large family room with a gas fireplace and cathedral ceiling, a bright sun room, and a brand new kitchen with stainless steel appliances and granite counter tops. The dining room is conveniently adjacent to the kitchen and has a table that comfortably seats 8 people. brbrThe sunroom opens out onto a 400 sq ft. mahogany deck with 2 retractable awnings. The deck leads to a large stone patio with a round gas fire pit and a built in outdoor kitchen including gas grill and sink. This is where the entertaining happens! Let the kids play on the custom all wood playground with shredded rubber Base while you relax around the fire pit. brbrThe newly finished, spacious lower level has an additional rooms including a second family room and a brand new bathroom/laundry room. Please ask for sheet and towel rental companies, if you don't wish to bring your own. We do not provide sheets or towels. brbrHome is set back on a large circular driveway, for privacy and kids safety... Feel free to use the beach chairs, board games, and beach toys. brbrThis home is surrounded by beautiful lakes and very convenient to town center, ocean beaches and the bay.

Bed

Bath

Sleeps

$1602.3

/ Nightly

Private Vacation Home

Enchanting Waterfront Summer Escape on Pleasant Bay

Orleans, Massachusetts, United States

Beautiful Pleasant Bay waterfront vacation home with 180 degree unobstructed views of the Pleasant Bay estuary. This vacation home is about light-filled rooms virtually all with a view of the water, kayaking, canoeing, sailing, fishing and more: a most unique, charming, enchanting yet substantial home in the Mayflower Point area. brbrWaterfront with deep water access, gentle path down to the sandy beach, first floor master suite, living room, open kitchen and dining, family room, all with water views; 3 decks from which to choose your sun or shade exposure. 4 bedrooms and 4.5 baths. brbrMain floor master bedroom with a king bed, second floor master has a queen size bed, a single bed and private bath. A third bedroom has a Queen size bed and bath down the hall. All three of these bedrooms have water views. brbrThe kitchen, located in the center of the house, is perfect for entertaining. Plenty of counter space and two sinks allow all guests to participate in preparing meals. brbrA separate rec room provides recreation space for playing Pool, watching movies or playing games. The rec room is in a separate building and has a full bath and may be used for overflow sleeping if needed.brbrOf course all of the basics are provided including a grill and plenty of outdoor furniture. There are two kayaks at the house that you're welcome to use. Linens and towels are included and provided through a professional linen service.brbrThe house is situated in a quiet rural neighborhood and is the perfect setting for a relaxing, waterfront experience.

4

Bed

4

Bath

6

Sleeps

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