House vacation rentals in Orleans

An aerial view captures a cottage nestled among vibrant green trees, showcasing the surrounding natural landscape. A glimpse of the ocean is visible in the distance. The cottage features a deck facing the woods, providing a serene and secluded ambiance.

5.0 out of 5 average rating, 33 reviews

Peaceful Nauset Beach Sanctuary

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. Chill out on the deck. Take a 10 minute walk to a private section of Nauset Beach or drive to our free association Nauset parking lot.

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5.0 out of 5 average rating, 12 reviews

10 min walk to Beach - Amazing View & Huge Deck

Enjoy an incredible view of Duck Meadow Tidal Marsh from this cozy cottage. Only a 10 minute walk to Boat Meadow Landing, a great bayside beach. Sip your morning coffee on our huge deck while enjoying the view. The deck includes a retractable roof if you would prefer to sit in the shade. Only minutes from incredible restaurants & shops in Orleans. This home includes AC, office space w/ monitors & a natural gas fireplace. Near the Cape Cod Rail Trail, hiking trails and numerous beach options!

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5.0 out of 5 average rating, 242 reviews

A historic home features classic New England architecture, with a peaked roof and wooden shingle siding. White trim outlines the windows and door, while a white picket fence surrounds the property. Lush greenery and colorful flowers enhance the welcoming exterior under a clear blue sky.

Home in Sandwich

Quintessential Waterfront Historic Cottage

Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

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4.97 out of 5 average rating, 59 reviews

A sunlit living area features large windows that provide views of the surrounding trees and nearby pond. A cozy circular chair invites relaxation, while a small dining table with black chairs offers a spot for meals. Green plants add a natural touch to the decor.

Home in South Dennis

Nehemiahs Nest: Healing Cape Cod Pond View Cottage

18+ Lovely waterfront tranquil getaway. All nearby houses hidden! This gem of a spot has been curated to soothe the soul! The cottage is sitting on Bakers Pond with an unobstructed view surrounded by conservation land *The driveway abuts a road* Wildlife can be observed. Swim or fish in this very clean kettle pond! The edges of the pond require water shoes for comfort as this is a natural body of water with no man-made beach/interference of nature. Kayaks, and life jackets available

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A charming beach house with shingle-style siding is displayed, set within a landscaped yard. Two large bushes frame the entryway, and the building features multiple rooflines and skylights. A brick pathway leads to the front door, with trees providing partial shade in the foreground.

4.97 out of 5 average rating, 116 reviews

Beachfront Charmer! Newly Renovated.

Steps to a beautiful sandy beach and just a mile to the heart of Chatham! This charming, newly renovated beach house has the amenities you need to make the most of your time with friends & family. Just 300 ft from Little Beach & a 5 minute walk to Chatham Lighthouse and Lighthouse Beach, we've made our new home the perfect place to gather and relax. All BRs and Living room have AC. Grill on the back deck, stroll to town, rinse off in the outdoor shower...this house has it all!

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A charming antique Cape Cod home is framed by a white picket fence and surrounded by lush greenery. The exterior features a gray wood shingle facade and multiple windows. Two red adirondack chairs are positioned on the front porch, inviting relaxation amidst the serene garden.

4.96 out of 5 average rating, 49 reviews

1850 Orleans Antique Home with Path to Arey’s Pond

Make memories at this private family and pet-friendly 3 BR Orleans antique Cape Cod home with access to Arey’s Pond. Kayak and paddle-board directly to Little Pleasant Bay and beyond. The property was once home to the town tavern on Old County Road en route to Orleans. Enjoy the wrap-around 3 season porch. Antique home with bath and other renovations that were recently completed. We want to share this unique property with those who appreciate the history. Please ask questions!

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A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

4.98 out of 5 average rating, 129 reviews

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

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A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.

4.97 out of 5 average rating, 173 reviews

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

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4.93 out of 5 average rating, 331 reviews

The cottage showcases a classic Cape Cod design, framed by greenery and a gravel pathway. A standalone structure is visible with a sloped roof and a front door lined with dark shutters. Sunlight casts a warm glow on the exterior against a clear blue sky.

Home in East Dennis

Cape Cod Cottage by the Bay!

Classic, beautifully crafted, newer cottage by Cape Cod Bay. All amenities. Stainless steel kitchen, Cathedral ceilings, Wide plank wood floors, water view. 2 min walk to one of the best beaches on the Cape! Quiet locale in the historic village of Quivet Neck, within East Dennis. 35 miles to Provincetown. I do not allow pets. I have family members with severe allergies who use the cottage. There is no AC at this cottage. I have 15 windows, 4 fans and an ocean breeze.

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A charming exterior of the Carriage House features weathered shingle siding and a cupola on the roof. Surrounded by landscaped gardens, the entrance showcases a well-kept pathway and a mix of greenery and blooming flowers, creating a welcoming ambiance.

4.96 out of 5 average rating, 202 reviews

The Sea Captain's Carriage House

The 1840s Carriage House has been beautifully remodeled. The first floor has a living room, dining area, kitchen, and powder room with washer/dryer. The backyard deck has seating for four and a Weber gas grill. Upstairs, the large, elegant bedroom features a king-sized bed, sitting area, reading nook/twin bed, writing desk, and ensuite bathroom with shower. The half acre property offers beautiful gardens for you to enjoy and a delicious outdoor shower.

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A spacious backyard is surrounded by trees and features a well-maintained lawn. The house is visible in the background, with a light-colored exterior and multiple windows. A hammock is suspended between two trees, creating a relaxed outdoor space.

4.94 out of 5 average rating, 32 reviews

Orleans, MA Luxury Getaway

Enjoy the best the Cape has to offer! Stay at this hidden gem in Orleans, MA. Easy access to Nauset Beach and Little Pleasant Bay. Large, luxurious, and family friendly with a big yard in a quiet neighborhood. Enjoy our gazebo, firepit, outdoor grill, outdoor patio dining, and outdoor shower. Inside, luxuriate in this 4 bed 4 bathroom with a modern kitchen, breakfast nook, dining room, and living room. Washer and dryer included in basement.

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A sandy beach area is shown, populated with visitors enjoying the sun and water activities. Small boats are visible in the distance, while people are seen wearing casual summer attire. Beach chairs and umbrellas are scattered throughout the shoreline.

5.0 out of 5 average rating, 29 reviews

The Chatham Bars White Foam House Steps From Beach

Settle back in one of the rocking chairs on the front patio and take in the views of the harbor. Charm and warmth abound in this Cape Cod cottage with Chatham Seaside Links located across the street. Leave the car and walk to local restaurants and shops. Watch band concerts at the park and bask in the views from the Chatham Lighthouse. Go for a long stroll along Claflin Landing Beach all the way to the Fish Pier and buy the day's fresh catch.

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Popular amenities for Orleans house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 100 reviews

Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

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4.96 out of 5 average rating, 140 reviews

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

Private Pool, near beaches, 3 BR/3 BA, Central Air

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The backyard features an inground pool illuminated at night, surrounded by wooden decking. Nearby, a shed with white shutters enhances the outdoor space, while lush greenery provides a serene backdrop.

4.93 out of 5 average rating, 40 reviews

5-bedroom Cape with a pool and yard games.

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4.86 out of 5 average rating, 22 reviews

The lighthouse features a round white structure topped with a lantern room. A spacious deck wraps around the building, accompanied by a well-maintained lawn and a decorative pumpkin. American flags are displayed, and the surrounding area includes additional nearby structures and views of the water.

Home in West Dennis

Jolly Captain Lighthouse

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A spacious backyard is featured, highlighting a refreshing oval pool surrounded by a textured patio. Lounge chairs are positioned for relaxation under the sun. Lush greenery and trees provide a natural border, while a well-kept lawn enhances the inviting outdoor space.

5.0 out of 5 average rating, 13 reviews

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!

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5.0 out of 5 average rating, 15 reviews

An expansive in-ground heated saltwater pool is surrounded by a spacious patio. A gazebo is situated nearby, framed by lush trees. Lounge chairs with umbrellas provide shaded seating, while a hammock offers a relaxing spot. The pool reflects the clear blue sky, creating a serene outdoor setting.

Home in North Eastham

Lovely villa w pool/hottub, central AC, near beach

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4.96 out of 5 average rating, 28 reviews

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

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5.0 out of 5 average rating, 8 reviews

Home in South Dennis

Modern Oasis, Heated Saltwater Pool, Beach, Golf

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Weekly house rentals

4.97 out of 5 average rating, 34 reviews

Close to Beach, Dog Friendly, Chatham Cottage

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5.0 out of 5 average rating, 44 reviews

Steps to Rock Harbor | AC, Deck, Outdoor Shower

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A charming white cottage is set amidst lush greenery and colorful flowering trees. A red door adds a pop of color to the front facade. The driveway is covered with gravel and bordered by well-maintained shrubbery, contributing to the inviting exterior.

4.95 out of 5 average rating, 22 reviews

Petite Antique, location, location, location

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5.0 out of 5 average rating, 19 reviews

Centrally located, Orleans house

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5.0 out of 5 average rating, 33 reviews

Spacious, close to beaches & Orleans village

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A charming cottage is surrounded by lush greenery and blooming blue hydrangeas. Sunlight filters through a tree providing shade to the front yard. The inviting entrance is framed by well-maintained landscaping, creating a serene outdoor ambiance.

5.0 out of 5 average rating, 16 reviews

Cape Escape!

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An outdoor seating area is presented with plush, striped furniture and a large firepit at the center. A bright turquoise umbrella provides shade, while the tranquil waterfront view showcases shimmering water and greenery. Potted flowers add a touch of color to the serene setting.

4.96 out of 5 average rating, 84 reviews

Waterfront★ Pvt Beach ★ On Bike Path ★Bikes★Kayaks

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A historic two-story Cape Cod home is surrounded by lush greenery and well-maintained landscaping. The exterior features a combination of dark wooden siding and classic shutters, with a welcoming front porch and neatly trimmed bushes flanking the entrance.

5.0 out of 5 average rating, 8 reviews

The Cape Escape

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Private house rentals

The exterior of a classic Cape-style house is showcased, featuring a well-maintained pathway of brick leading to the entrance. Lush greenery surrounds the home, complemented by colorful blooming flowers, including vibrant red azaleas.

4.83 out of 5 average rating, 6 reviews

Beach Road pearl. 1 mile to Nauset Beach

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5.0 out of 5 average rating, 8 reviews

Aerial view of a beach house situated near the shoreline, showcasing a spacious lawn and landscaping. Calm waters and a sandy beach extend along the coast, with the property positioned for optimal water access. The nearby neighborhood is visible in the background.

Home in West Yarmouth

Sunset on Shore - Lewis Bay Waterfront

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4.98 out of 5 average rating, 57 reviews

A hot tub, installed in 2023, is located outdoors, surrounded by lush greenery. A wooden fence provides privacy, while colorful drink glasses rest on the edge, inviting relaxation. The clear water glistens under natural light, creating a serene atmosphere for guests.

Home in North Eastham

Priv. Hot Tub-King Bed-Fireplace-Season pond view

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The exterior of the home showcases a charming coastal design, featuring white siding and blue shutters. A neatly landscaped front yard contains low hedges and fresh mulch, with stone pathways leading to the entrance. Solar panels are visible on the roof, emphasizing eco-friendly features.

4.94 out of 5 average rating, 17 reviews

Luxe Holiday in Orleans! 5BR Beach, Hot Tub, Bikes

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A modern kitchen is presented, featuring stainless steel appliances and sleek cabinetry. A skylight allows natural light to fill the space. The countertops are finished in a light tone, complemented by a neutral backsplash. A window offers a view of the outdoors.

4.94 out of 5 average rating, 31 reviews

7th Vacation in Harwich

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An outdoor seating area features a circular table surrounded by eight cushioned chairs, providing a comfortable space for gatherings. A shaded umbrella offers protection from the sun, and a stylish fire pit is centrally located on a patterned outdoor rug.

4.97 out of 5 average rating, 36 reviews

Stunning Cape Cod Escape

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A spacious outdoor patio features a cozy seating area with comfortable cushions, surrounded by lush trees. A scenic view of the peaceful lake is visible in the distance, framed by the greenery. The inviting stone surface complements the natural surroundings.

4.83 out of 5 average rating, 12 reviews

Lake House with Private Lake Access

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An aerial view showcases a large estate set against a tranquil bay. The property features a sprawling lawn, with a red building juxtaposed against a neighboring white house and lush trees. The calm waters reflect the clear blue sky, enhancing the serene ambiance of the area.