House holiday rentals in Orleans

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Top-rated house rentals in Orleans

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
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.
Home in Harwich Port
4.98 out of 5 average rating, 112 reviews

Lg Modern beach& Wychmere, AC, fast WIFI, king bed

Entire spacious newly renovated modern cottage in Harwich Port. Sun filled open concept living room with a large kitchen island. Great for families ! Less than 4 min drive to Red River beach and Bank street Beach. 3 min drive to Wychmere Beach Club wedding venue. Close to Harwich Port downtown. Centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy a hike to Harwich Thompson's field Conservation area. Close to bike trail

Guest favourite
The exterior of The Drake Cottage is surrounded by lush greenery and a well-landscaped yard. The charming two-story structure features a mix of wood and stone siding, complemented by a gravel driveway leading to the entrance. Natural stones and native plants are arranged in the gardens.
Home in Brewster
4.83 out of 5 average rating, 197 reviews

The Drake Cottage - Brewster Beach Getaway

Experience quintessential Cape Cod in The Drake Cottage located right on 6A in Brewster, Ma. The Drake Cottage is conveniently situated within a mile of Drummer Boy Park, The Cape Museum of Natural History, Paines Creek Beach and a 9 min drive from Oceans Edge. The cottage offers an expansive private back yard with an acre of land. Enjoy a newly extended patio complete with fire pit, 10 person picnic table and BBQ grill. Our newly updated interior provides our guests with many modern amenities.

Top guest favourite
An outdoor gathering area is arranged around a circular fire pit, with several comfortable chairs and accent tables. The surrounding garden is filled with lush greenery and vibrant blue hydrangeas. Soft lighting enhances the cozy ambiance as twilight descends.
Home in Orleans
4.99 out of 5 average rating, 96 reviews

Modern Cape Escape Retreat- Walk to Pilgrim Lake

➤ Relax by the Outdoor Fire, stay in for a Family Movie Night, or explore Orleans’ nearby Beaches/Shopping/Dining ➤ Central: ★ Walk to Pilgrim Lake ★ 5mins drive to Beaches/Shopping ➤ Nestled in the peaceful windswept woodlands of the Lower Cape, this bright & spacious home is the ideal place for calm, connection & conversation ➤ A favorite of Family Holidays, Friends groups & Freelancers, this recently-renovated Orleans acreage transports you to a simpler time-where stress is left behind.

Guest favourite
The exterior of a classic Cape Cod house is shown, featuring shingle siding and multiple large windows. The surrounding landscape includes manicured shrubs and a gravel driveway, alongside a tree-lined backdrop that provides a natural setting. The entrance, framed by steps, leads to the welcoming front door.
Home in North Eastham
4.9 out of 5 average rating, 101 reviews

Large, cozy, walk to beach, central AC, game room

This classic, large Cape Cod house is just perfect for friends or a family reunion. The beautiful Thumpertown Beach is 0.3 miles or a 5-10 min slow stroll down the street. The house is large enough to accommodate everyone comfortably and has a convenient layout that also provides plenty of privacy. There is central A/C that covers the entire house, all rooms have hardwood floors, newer beds, comfortable mattresses and quality pillows. New 18x24 deck has Polywood furniture and Weber gas grill.

Top guest favourite
A waterfront hot tub is set against a natural backdrop of trees and calm waters. Inside, a dining area features a large window with views of the lake. A cozy living room displays comfortable seating, while an outdoor patio has seating for relaxation and enjoying the scenery.
Home in South Yarmouth
4.95 out of 5 average rating, 255 reviews

Waterfront Spa|Hot Tub+Cold Plunge in Lake|King bd

✅All linens provided & beds made ✅ King bed / Queen / Twin over Full bunk ✅ Direct lake access = natural cold plunge Follow with hot tub recovery! ✅Waterfront hot tub for 6 -Open year round ✅Fully kitchen w/Carrera marble counters ✅Large waterfront dining rm ✅Gas Fireplace in living rm ✅Level backyard to lake ✅Dock for swimming & fishing ✅2 kayaks & 2 SUPs / beach chairs ✅Deck w/sitting & dining area ✅Patio w/seating & gas fire pit ✅Pet fee $30/day ✅W/D Locally managed

Guest favourite
A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.
Home in Chatham
4.95 out of 5 average rating, 298 reviews

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Top guest favourite
The exterior of a charming cottage is visible, featuring natural cedar shingles and a welcoming porch. Lush flower beds, including vibrant blue hydrangeas, frame the entrance, while a white picket fence adds to the quaint appeal. A well-maintained lawn enhances the home's inviting presence.
Home in Brewster
4.92 out of 5 average rating, 106 reviews

Antique Cape Home With Modern Conveniences

The Elisha Howland Saltbox provides your opportunity to experience the unmatched essence of a true 'Olde Cape Cod' home. We offer a restored antique Saltbox with 2 bedrooms and 2 bathrooms. For an additional charge, there is a detached cottage which can accommodate two more guests. PLEASE NOTE: we accept ONLY FULL WEEK RENTALS from mid-June to mid-September, but we welcome shorter or much longer stays during the rest of the year. Our home is a lovely place to spend a winter on Cape Cod.

Top guest favourite
A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.
Home in Dennis Port
4.96 out of 5 average rating, 218 reviews

Lakefront House/Private Dock/Year Round Hot Tub/AC

Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

Top guest favourite
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
4.93 out of 5 average rating, 318 reviews

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.

Superhost
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.
Home in Eastham
4.96 out of 5 average rating, 193 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.

Top guest favourite
An outdoor dining setting features a table with a plate of salad and wine glasses, accompanied by a bottle of white wine. In the background, a charming shed displays ‘Cape Away’ signage, surrounded by well-maintained greenery and a cozy lounge area.
Home in South Yarmouth
5 out of 5 average rating, 183 reviews

Relax in Comfort w/ King Beds, Sauna, Coffee Bar

Cape Away is a cozy, family & pet friendly retreat in the charming Mid-Cape region. Start your mornings with coffee in the fully stocked kitchen, hit up nearby beaches, then unwind in the sauna, outdoor shower, or by the fire. With games, private fenced backyard, shed bar and fast WiFi, you’re 5–10 minutes from top restaurants and beaches. Book now and make your Cape Cod memories here.

Top guest favourite
A serene outdoor seating area is set by the waterfront, featuring two chairs with teal cushions and a white table. Lush greenery surrounds the area, enhancing the view of the calm waters and trees beyond. Lanterns add a subtle decorative touch to the space.
Home in Yarmouth Port
4.99 out of 5 average rating, 370 reviews

Fabulous Waterfront with Spectacular Sunset Views!

**Waterfront on salt water Follins Bay which is the headwaters of the Bass River. Sit and watch the boat activity from the deck or patio. Swim, fish or kayak (2 provided) right from your the backyard on your own private dock. Bright & airy décor with beautiful water views.

Popular amenities for house rentals in Orleans

When is the best time to visit Orleans?

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Avg. price$532 SGD$516 SGD$465 SGD$503 SGD$482 SGD$561 SGD$714 SGD$738 SGD$489 SGD$465 SGD$514 SGD$507 SGD
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Quick stats about house rentals in Orleans

  • Total holiday rentals

    Explore 320 holiday rentals in Orleans

  • Nightly prices starting at

    Orleans holiday rentals start at $90 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,670 verified reviews to help you choose

  • Family-friendly holiday rentals

    300 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 120 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wifi availability

    320 of Orleans holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Orleans rentals

  • 4.8 Average rating

    Orleans stays are highly rated by guests – averaging 4.8 out of 5!