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Waterfront vacation rentals in Chatham

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Chatham

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

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Rental unit in Wellfleet

4.86 out of 5 average rating, 119 reviews

Calypso #2 - Sept/Oct Special Rates

Sept/Oct are beautiful in Wellfleet! Enjoy special rates! Wellfleet Harbor on Duck Creek. 5 minutes from the village. Self-contained, gorgeous 2nd floor flat in 2 century-old whale merchant's home on Duck Creek. Steps from restaurants, the town pier, Mayo Beach & Main Street. Perfect for active types who prefer to walk instead of drive. Ideal for kayakers & bikers. Best location in Wellfleet. We have 5 flats in this house all found on Airbnb. If this one is booked, inquire here for more info.

Home in Hyannis Port

4.98 out of 5 average rating, 105 reviews

Beautiful Private Beach House

One of a kind extraordinary waterfront rental. Wake up to the most spectacular views of the Ocean and enjoy watching the sun set over the Kennedy Compound. Build sand castles on your own private beach while watching sail boats set off to Nantucket. This home is quintessential for a family vacation or romantic getaway. Located in central Hyannis Port with easy access to down town dining, shopping, and the Hyannis harbor. PLEASE read our rules and before booking there are important requirements.

Home in Sandwich

5 out of 5 average rating, 186 reviews

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.

Cottage in Tisbury

4.98 out of 5 average rating, 45 reviews

WATERFRONT Cottage, Downtown w/ Beach

DIRECT WATERFRONT in-town beach house with walk-out beach and onsite private parking. This recently renovated 1 bedroom, 1.5 bath, 2-story house is located directly across the street from the famous Black Dog Tavern, right on the bustling year-round Vineyard Haven harbor. This property is no doubt one of the most unique residential properties on Martha’s Vineyard given its proximity to the harbor, ferry terminal, stores, restaurants, bike rentals, beaches & so much more. You will love it!

Home in West Yarmouth

5 out of 5 average rating, 281 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

Home in Dennis Port

4.95 out of 5 average rating, 172 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.

Home in North Falmouth

5 out of 5 average rating, 14 reviews

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

***WATERFRONT LUXURY HOME*** Ideal Monthly Stay for Large Family 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

Home in Mashpee

5 out of 5 average rating, 3 reviews

2BR Waterfront Beauty on Sandy Beach

Beachfront Location: Direct access to John’s Pond with a sandy beach, close to Falmouth, Martha’s Vineyard, and Hyannis. Flexible Stays: Weekly discounts, midterm rentals, and seasonal winter options. Ideal for fall getaways. Group Friendly & Amenities: Rent up to 4 units, each for 4 guests. Enjoy canoes, a communal beach area with kayaks, canoes, a picnic table, BBQ/fire pit, and chairs. Perfect for larger parties. Contact us for custom bookings!

Home in South Dennis

4.87 out of 5 average rating, 507 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

Home in West Yarmouth

4.94 out of 5 average rating, 31 reviews

LUXURY WATERFRONT HOME - Private Dock - Near Beach

Renovated 3 bedroom waterfront home on Parkers River with private dock including (3) brand new kayaks and stand up paddleboard to use in the backyard. Property was recently updated with central air and a brand new kitchen. Short four minute walk to the beach or take the kayaks over to Lewis Pond or Seagull Beach. Mini golf, restaurants and driving range just down the street. Brand new furniture throughout!

Rental unit in Dennis Port

4.82 out of 5 average rating, 22 reviews

Serene One-Bedroom Riverside Haven

Relax for the week at this peaceful waterfront cottage unit right on Swan River in Dennisport! Bring your kayaks and launch them into Swan River from the shared backyard dock or float down Swan River into South Village beach. Explore Cape Cod and see what Dennisport has to offer while staying at this unique waterfront haven! Available weekly summer rentals and 3-night minimum stays in the off- season

Rental unit 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)

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

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Hotels

Stylish accommodations and amenities

Popular amenities for Chatham waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Rental unit in Sagamore Beach

4.97 out of 5 average rating, 114 reviews

Cape Cod Canal Home

Rental unit in Woods Hole

4.89 out of 5 average rating, 81 reviews

On Eel Pond: Woods Hole Waterfront Retreat

Rental unit in Eastham

4.93 out of 5 average rating, 180 reviews

King bed/Hot Tub/Waterfront-The Lotus

Rental unit in Wareham

4.91 out of 5 average rating, 160 reviews

☀️ Spacious and Bright -- The Sailboat Suite

Rental unit in Plymouth

4.82 out of 5 average rating, 358 reviews

The Harbor House - In The Center of Downtown

Rental unit in East Orleans

4.95 out of 5 average rating, 288 reviews

Cozy Waterfront Apartment, Private Beach Access

Rental unit in Plymouth

4.97 out of 5 average rating, 32 reviews

Penthouse with Private Roofdeck on Plymouth Harbor

Rental unit in Wareham

5 out of 5 average rating, 9 reviews

Lovely, Spacious Onset Beach Studio Amazing Views!

Waterfront house rentals

Home in Wareham

4.9 out of 5 average rating, 20 reviews

Waterfront Home in Onset for Happy Memories

Home in New Seabury

5 out of 5 average rating, 7 reviews

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

Home in Marstons Mills

4.91 out of 5 average rating, 177 reviews

Lake Front Stunning Cape Cod Views w Private Beach

Home in Plymouth

4.93 out of 5 average rating, 81 reviews

Waterfront New Cottage Private Beach

Home in Plymouth

4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

Home in Brewster

4.88 out of 5 average rating, 193 reviews

Water Front Pond House - 3 acre Cape Cod Sanctuary

Home in Falmouth

4.95 out of 5 average rating, 88 reviews

Private Waterfront Home on Picturesque Pond

Home in Mashpee

5 out of 5 average rating, 6 reviews

Escape to cape/water front home

Waterfront condo rentals

Condo in Dennis Port

4.92 out of 5 average rating, 26 reviews

Studio steps to a private beach!

Condo in Plymouth

4.95 out of 5 average rating, 65 reviews

Lovely Suite w/ Balcony Overlooking Harbour!

Condo in Dennis Port

4.8 out of 5 average rating, 5 reviews

2BR Presidential Cape Cod Resort Ocean Front

Condo in West Dennis

4.89 out of 5 average rating, 28 reviews

1BR 2nd Floor Condo with pool

Condo in Chatham

4.86 out of 5 average rating, 88 reviews

Steps to Private Beach in Chatham

Condo in West Dennis

4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

Condo in Oak Bluffs

4.96 out of 5 average rating, 27 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Condo in Plymouth

5 out of 5 average rating, 106 reviews

Captain's Lodge- #1, Plymouth Water Front Condo

Quick stats about waterfront rentals in Chatham

Total rentals
60 properties
Nightly prices starting at
$140 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

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