Waterfront holiday rentals in Chatham

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Top-rated waterfront rentals in Chatham

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

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Top guest favourite

Home in South Yarmouth

4.94 out of 5 average rating, 236 reviews

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK

✅All linens provided & beds made ✅Smart TVs in living rm & 2 bdrms ✅Waterfront hot tub for 6 -Open year round ✅Fully equipped kitchen w/Carrera marble counters ✅Large waterfront dining rm ✅Gas Fireplace in living rm ✅High quality down comforters & pillows ✅Level backyard to lake - great for games ✅Dock for swimming & fishing ✅2 kayaks & 2 SUPs / beach chairs ✅Deck w/sitting & dining area ✅Patio w/seating & gas fire pit ✅Sleeps 7 ✅Pet fee $30/day ✅Waterfront ✅W/D Locally managed

Guest favourite

Cottage in Sandwich

4.95 out of 5 average rating, 229 reviews

WOW VIEW! Waterfront w/ Private Beach, King Bed!

Wake up to magnificent panoramic views of a beautiful lake with waves lapping below your window! Search on YouTube for tour: "WOW View! Cape Cod Lakefront Cottage. Private Beach, King bed" Guests love this stylish and open cottage on the shore of a large recreation lake with its own private beach. Wall-to-wall floor-to-ceiling windows with a new modern kitchen, luxurious King gel/coil bed, office space, bathroom with curved shower, and much more! It's like being on your own luxury houseboat!

Top guest favourite

Cottage in Yarmouth

5 out of 5 average rating, 219 reviews

Serenity Views | Waterfront | KingBed | Kayaks SUP

Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Comfortably hosts 2 families. Wake up to incredible sunrises. Lounge on the hammock or swim/fish/kayak in our beautiful backyard waterfront Long Pond. Explore the Cape in each direction: beautiful beaches and endless fun activities/interests. At the end of the day, enjoy dining on the deck as you grill. Sit back on the patio with a cocktail and gaze at the star filled sky and ambiance from the fire table. Welcome!

Superhost

Home in Brewster

4.87 out of 5 average rating, 210 reviews

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

Top guest favourite

Guest suite in Chatham

4.99 out of 5 average rating, 240 reviews

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table just steps to a 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 downtown Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

Guest favourite

Home in Plymouth

4.93 out of 5 average rating, 148 reviews

Panoramic ocean views 100 ft above Cape Cod Bay

Our 5-bdrm Nantucket style beach house has a new kitchen & open living space, with a new deck, all overlooking the entire shoreline of Cape Cod Bay from a commanding perch atop a 100-foot bluff. Whales and seals can be seen from your deck. Located in a private community with its own rocky beach access about 5 min walk from the house where you can hunt for shells & observe the ocean wildlife. This beach is ideal for kayaking. Plymouth also boasts 4 of top 10 rated public golf courses in MA.

Guest favourite

Home in Chatham

4.95 out of 5 average rating, 279 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

Home in Dennis Port

4.96 out of 5 average rating, 199 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.

Guest favourite

Cottage in Eastham

4.95 out of 5 average rating, 240 reviews

The Breeze Overlooking Minister's Pond

The Breeze is a luxurious, romantic cottage by a serene freshwater pond, surrounded by vibrant gardens. Perfect for a peaceful getaway, enjoy kayaking, canoeing, and relaxing on the dock, or explore nearby trails and the Cape Cod Rail Trail with provided bikes. Unwind with evenings by the fire pit, refreshing outdoor showers, and a plush queen bed for ultimate comfort. This private oasis offers tranquility, natural beauty, and 5-star attention to detail for your perfect escape.

Superhost

Cottage in South Dennis

4.88 out of 5 average rating, 419 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!

Guest favourite

Guest suite in East Orleans

4.92 out of 5 average rating, 184 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.

Guest favourite

Apartment in Chatham

4.86 out of 5 average rating, 103 reviews

Steps to Private Beach in Chatham

2 Bedroom condo with views of the beach, ocean and marina. This wonderful condo is part of a beachfront/oceanfront complex, with steps to your own private beach in Chatham! We are within a mile of beautiful downtown Chatham and within a short walk to Chatham’s famous lighthouse beach and Monomoy Wildlife refuge. Whether by land or sea, there's something for everyone. This is a great place to make memories.