Waterfront holiday rentals in Orleans

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Orleans

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

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Guest favourite

Cottage in Eastham

4.95 out of 5 average rating, 207 reviews

The Breeze Overlooking Minister's Pond

Welcome to an absolutely spotless, pristine, romantic cottage directly on a freshwater pond. Centrally located in beautiful Eastham, the Breeze is within walking distance to the Salt Pond Museum and Visitor Center and hiking trails. Take one of the electric bikes provided and hop on the bike path (the CCRT) which is just down the street. Kayak or canoe on the pond. Featured on WNAV "Romantic Winter Getaways". Award winning recommendations guide provided with each stay. *Sat-Sat in July & Au

8–15 Oct

$360 SGD per night

Guest favourite

Home in South Yarmouth

4.93 out of 5 average rating, 209 reviews

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK

✅ We keep rates low by you bringing your own sheets & towels OR linen service is $125. ✅ Smart TVs in LIving Room & 2 BRs ✅ Waterfront hot tub-Open year round ✅ Fully equipped kitchen w/Carrera marble countertops ✅ Gas Fireplace in LR ✅ High quality down comforters & pillows ✅ Level backyard to lake ✅ Dock for swimming and fishing ✅ 2 kayaks & 2 SUPs ✅ Deck w/sitting & dining area ✅ Patio w/seating & gas fire pit ✅ Sleeps 7 ✅ Pet fee $30/day ✅ Waterfront ✅ W/D Locally managed

16–23 Jan

$498 SGD per night

Guest favourite

Guest suite in Chatham

4.99 out of 5 average rating, 203 reviews

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table, private access to the fresh water pond, outdoor shower. The friendly, cottage-style decor is inviting w/queen-size bed, couch, ample closets, private bathroom w/shower, small dining area w/microwave & fridge (no stove, no bbq); writing table, WiFi, Roku & DVD player. Enjoy the water view! Minutes by car to Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

6–13 Oct

$348 SGD per night

Guest favourite

Home in Chatham

4.95 out of 5 average rating, 241 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.

4–11 Dec

$580 SGD per night

Guest favourite

Home in Yarmouth

5.0 out of 5 average rating, 248 reviews

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi

20–27 Sep

$782 SGD per night

Guest favourite

Home in Dennis

4.95 out of 5 average rating, 151 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.

9–16 Nov

$342 SGD per night

Guest favourite

Flat in East Orleans

4.94 out of 5 average rating, 259 reviews

Cozy Waterfront Apartment, Private Beach Access

Hello to all of my future guests. I want to wish you all well and safety in these uncertain times. I can assure you that this property is safe, private, spotless and affords you access to a beautiful private beach. I have updated the apartment to include a microwave and two kayaks. We are implicating extra sanitizing and cleaning measures to ensure the apartment is clean and safe for each guest! Please stay safe, optimistic, and let me know of any concerns. Sincerely, Patty

4–11 Oct

$297 SGD per night

Guest favourite

Home in Chatham

4.96 out of 5 average rating, 101 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.

26 Dec – 2 Jan

$420 SGD per night

Guest favourite

Cottage in Sandwich

4.95 out of 5 average rating, 160 reviews

Waterfront Lake Cottage, Private Beach, Wow View!

Wake up to a magnificent view of a beautiful lake with waves lapping gently below your window! Guests love this stylish and open designed home dramatically located on the shores of a large, recreational lake. It's like being on your own luxury houseboat! Enjoy the wall-to-wall windows with a panoramic view, a beautiful new modern kitchen, your own private beach, a new luxurious King hybrid gel/coil bed, private office space, large bathroom with curved shower, and much more!

26 Feb – 5 Mar

$514 SGD per night

Superhost

Cottage in Dennis

4.88 out of 5 average rating, 352 reviews

Waterfront Cottage on White Pond(Graham Cracker)

Our cottage (Graham Cracker House) sits steps from crystal clear White Pond. The cottage offers private access to the pond for swimming, fishing and boating. The large outdoor space is great for dining and relaxing by the pond. It is 1.5 miles to the Cape Cod rail trail (bike trail), close to many dining options and 3 miles to some of the best beaches Cape Cod has to offer. There is another cottage on the property for rent that sleep 4 guests. No sharks here!

23–30 Apr

$275 SGD per night

Guest favourite

Guest suite in Orleans

4.92 out of 5 average rating, 143 reviews

Charming Old Cape Cod

Relax and enjoy spending time at Snowtop on the Town Cove, many activities including sailing, paddle boarding, water skiing and spectacular sunsets! A short walk to swim, sit on the sand or take a beach walk. The offered space has a private entrance with bath, bedroom with a king size bed, a sunny living room with dining table over looking the water where you could choose to dine in, have coffee in the morning or play a game.

3–10 Oct

$176 SGD per night

Guest favourite

Guest suite in Orleans

4.99 out of 5 average rating, 205 reviews

Private Beach, Cozy Cape Cottage

Enjoy your own private beach with soaring seabirds and ocean breeze! Let a breathtaking sunrise and view of the bay greet you every morning from bed. Take in the waterfront view on the outside patio by the garden or in the enclosed sun porch. Escape to our cozy cottage secluded in the woods with nearby trails. Explore the Cape's many attractions and refresh your soul with a relaxing Cape Cod vacation.

10–17 Mar

$378 SGD per night