Waterfront vacation 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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Guest favorite

Two lounge chairs are positioned on a private deck overlooking the harbor, accompanied by a small side table. The clear blue sky and calm water create a serene backdrop, with distant boats gently bobbing in the waves.

Condo in Provincetown

4.93 out of 5 average rating, 148 reviews

Westend Waterfront Luxury Condo-Provincetown

Waterfront condo in heart of the west end. Open-air design with multi-window views of the harbor, Long Point, and distant shores. Galley kitchen with breakfast bar, beautifully tiled bath, both renovated in a contemporary fashion. Includes one parking space (SMALL/MID-SIZED car only). Second-floor end unit has abundant light, water views, exclusive deck.Common deck access is not available.7 days min high season Jun28-Aug30 Sat-Sat only! NO PETS! NON SMOKING CONDO COMPLEX! NO EARLY CHECK INS.!

Superhost

A charming cottage with a red roof sits alongside the water, surrounded by lush greenery. A small boat is moored nearby, and seating is available by the cottage. The scene captures a serene outdoor environment, inviting exploration and relaxation.

Cottage in Wareham

4.86 out of 5 average rating, 148 reviews

Onset beach, Cape code.Private Waterfront cottage

PRIVATE LAKE FOR YOUR Vacations year around. Spend quality time on spectaculars Blackmore pond.Comfortable cottage,step away from the water.Your own big dock out of your house as you wake up .Enjoy sunshine and sunset during summer , beautiful foliage , experience the ice or Snow drop during winter. this is exceptional romantic for your family . Well located next Onset beach, Water Park , Water Wizz of Cape Code. , Gate to Cape , To Ferry to Nantucket, Martha vineyard, Plymouth to P-Town

Top guest favorite

The exterior of the cottage features a patio area with a gas grill, leading to a serene waterfront view of the pond. Lush green trees frame the space, providing a natural backdrop, while a small clock is mounted on the wall near the entrance.

Home in West Yarmouth

5 out of 5 average rating, 304 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

Top guest favorite

Two teal Adirondack chairs sit on a wooden deck, facing a tranquil water view. Lush greenery surrounds the area, and the sky is partly cloudy, creating a serene outdoor space perfect for relaxation.

Home in Dennis Port

4.96 out of 5 average rating, 193 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 favorite

A serene view of Wing Pond displays calm waters reflecting scattered clouds and a vibrant sky. The lush greenery along the shoreline is visible in the background, creating a natural border that enhances the tranquil atmosphere of this waterfront location.

Home in North Falmouth

5 out of 5 average rating, 15 reviews

Luxury-Waterfront-Pets OK-Large Family-Bike Path

***WATERFRONT LUXURY HOME*** Ideal For Multiple Families Pet Friendly Picturesque Wing Pond Kayaks (kids and adult), SUP'S, Row Boat, fishing Bike Path out front door Waterfront Outdoor Dining for 12 Soaring 9-18 ft. ceilings Waterfront Indoor Dining for 10 Chef Kitchen 18 Foot Kitchen Island Wolf/Viking/Miele Appliances Walk in Pantry Waterfront floor to ceiling windows 4,000+ SQ FT Lux Beds/Bedding Business Class Wifi Oversized Stone Fireplace Waterfront Master Suite

Guest favorite

An outdoor seating area features a comfortable sectional sofa adorned with various cushions. A wooden coffee table sits at the center, holding a floral arrangement. The backdrop includes windows and landscaping, creating a serene setting on the waterfront deck.

Home in Provincetown

5 out of 5 average rating, 11 reviews

Breathtaking Waterfront Rental

Sun kissed waterfront two story condo with 2 expansive private decks right on the bay within the heart of Provincetown, with beach access! Offers many options to relax and have fun in this iconic town! Centrally located. 7 min walk to Boat Slip or Crown & Anchor, 5 min walk to MacMillan Wharf (perfect if arriving by ferry). Enjoy the serenity of the East End, steps away from Mews & Strangers & Saints. Relish at your own beach, bike to Herring Cove or Race Point!

Top guest favorite

A spacious wooden deck offers lounge chairs and a dining area, with potted flowers adding color. The ocean is visible in the background, with boats in the distance against a clear blue sky.

Condo in Provincetown

4.92 out of 5 average rating, 325 reviews

Beachfront Town Center

Waterfront condo association in the center of Provincetown, close to everything! This studio is located in Angels Landing and has everything you need for your stay in Provincetown. Steps from the beach, shopping, coffee shops, restaurants and galleries. The studio offers large waterfront decks with chairs for lounging and an outdoor shower to complete your beach front vacation! Parking is not included, but you can find parking info on the towns website.

Superhost

A deck extends from the cottage, featuring a small outdoor dining area with wooden chairs and a table. The serene waters of White Pond reflect the surrounding greenery, and a chimney is visible on the side of the cottage, adding to the rustic charm.

Cottage in South Dennis

4.87 out of 5 average rating, 516 reviews

Beachfront Cottage on White Pond (Marshmallow)

Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

Superhost

The open living space features large windows providing direct views of Cape Cod Bay. A light-colored sectional sofa is positioned to maximize views, while a ceiling fan offers air circulation. The room's modern decor is complemented by natural light streaming through the windows.

Condo in Provincetown

4.9 out of 5 average rating, 29 reviews

Spectacular Waterfront Condo

Enjoy direct water views of Cape Cod Bay in our beautiful 1st floor condo with central air. Our home is steps from the beach with an approx. 1 mile walk through the dunes to the Atlantic Ocean. We are perfectly situated on the East End with beach accessibility. Enjoy Provincetown’s great restaurants, many art galleries, shows and unique shops. Enjoy our home anytime of the year.

Superhost

A charming waterfront building with a distinct blue facade features multiple balconies lined with railing. A lively outdoor dining area is visible on the lower level. Surrounding structures reflect a lively coastal atmosphere, with clear skies and people enjoying the vibrant setting.

Apartment in Oak Bluffs

4.88 out of 5 average rating, 153 reviews

WATERFRONT PENTHOUSE OAK BLUFFS

3rd fl Waterfront Oak Bluffs Harbor Penthouse- Sleeps 2 comfortably-3 in a pinch. (356sqft) . Queen bed & a reclining futon couch. With kitchenette & amazing harbor views, you cannot get closer to harbor, unless you fell in. Located above a seasonal restaurant, with 5 open air restaurants (2 on each side, & were in the middle with our restaurant Lobsterville Bar & Grille below)

Superhost

A serene waterfront view showcases a collection of cottages nestled along the shoreline, surrounded by lush greenery. The calm water reflects the vibrant landscape, with a gentle shoreline leading to a well-maintained yard space. The clear sky adds to the tranquility of the scene.

Home in Orleans

4.89 out of 5 average rating, 57 reviews

Romantic Orleans waterfront cottage

ENHANCED CLEANING/DISINFECTING and SELF CHECK-IN ! The best of Cape Cod - literally on the edge of the gorgeous and picturesque saltwater town cove! This beautiful 1BR cottage is clean, comfortable and private, ... yet within a short walk to village center, shops, great eateries, attractions, etc. We just added propane fire pits and bluetooth speakers outside!!

Guest favorite

An aerial view captures the layout of Onset, Massachusetts, featuring sandy beaches, waterways, and a scenic village. The landscape reveals a mix of homes, trees, and beach areas, with the coastline gently curving along the shore.

Home in Wareham

4.89 out of 5 average rating, 245 reviews

The Light House - on the water, secluded, kayaks

On the water on private quiet cul de sac with breathtaking views & two decks. Just 3/10 of a mile walk to 2 beaches & Onset village with great restaurants & attractions. Kayak right from our backyard. Kayaks provided! Hot/cold outside shower. Outdoor deck dining. Dishwasher, Washer, dryer, WIFI. Window AC units in all bedrooms. Onset, the gateway to Cape Cod.