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Waterfront vacation rentals in Chatham

Find and book unique waterfront accommodations on Airbnb

Top-rated waterfront accommodations in Chatham

Guests agree: these waterfront accommodations 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.

Guest favourite

Home in Marstons Mills

4.91 out of 5 average rating, 177 reviews

Lake Front Stunning Cape Cod Views w Private Beach

Stunning Cape Cod vacation home in Cotuit. Beautiful lake front property. bright, spacious. Private lake beach w fire pit. Large deck with grill overlooking the water. Parking pass to many ocean beaches just a couple minutes away. Nearby beach, ocean beach, trails, shops, restaurants, golf, gym nearby ... Lake is great for swimming, fishing, canoeing and kayaking. Most rooms in the house have a full lake view. (All but one.) Close to Osterville, Centerville, Mashpee, Falmouth and Hyannisport.

Guest favourite

Rental unit in Wareham

4.85 out of 5 average rating, 123 reviews

⭐ Amazing Onset Getaway in the Starfish Suite

The spacious and comfortable Starfish Suite is in an amazing location just steps away from Onset Beach, village, boat rentals, market, & restaurants! Located on the second floor of a renovated Sea Captain's house, this large apartment gets great natural light. A/C included in all bedrooms. Fully stocked kitchen. Fiber WiFi & Smart TV. Nice covered deck with park and bay views. One of the very best locations in Onset! Pet friendly as well 🙂 Perfect spot for a beach getaway or family vacation.

Guest favourite

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.

Guest favourite

Cottage in East Falmouth

4.93 out of 5 average rating, 158 reviews

“Cozy Cottage” on Great Bay

Due to the coronavirus, we’re taking extra care to disinfect frequently touched surfaces between reservations.” Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach.We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.

Guest favourite

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

Guest favourite

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.

Guest favourite

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!

Guest favourite

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 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)

Guest favourite

Cottage in Harwich Port

4.96 out of 5 average rating, 23 reviews

Beautiful 1BR Steps to Wychmere Harbor & Beach

Unwind in this well appointed tranquil, coastal apartment. Located steps from a private beach, Wychmere Beach Club, a picturesque harbor, the Freedom Ferry to Nantucket and downtown Harwich Port. This newly constructed apartment is the perfect place for a getaway. With finishes resembling a high end hotel, guests are sure to feel comfortable in this luxury abode.

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Popular amenities for Chatham waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Guest favourite

Rental unit in Sagamore Beach

4.97 out of 5 average rating, 114 reviews

Cape Cod Canal Home

Guest favourite

Rental unit in Woods Hole

4.89 out of 5 average rating, 81 reviews

On Eel Pond: Woods Hole Waterfront Retreat

Guest favourite

Rental unit in Eastham

4.93 out of 5 average rating, 180 reviews

King bed/Hot Tub/Waterfront-The Lotus

Guest favourite

Rental unit in Plymouth

4.82 out of 5 average rating, 358 reviews

The Harbor House - In The Center of Downtown

Guest favourite

Rental unit in East Orleans

4.95 out of 5 average rating, 288 reviews

Cozy Waterfront Apartment, Private Beach Access

Rental unit in Dennis Port

4.82 out of 5 average rating, 22 reviews

Serene One-Bedroom Riverside Haven

Guest favourite

Rental unit in Wareham

5 out of 5 average rating, 9 reviews

Lovely, Spacious Onset Beach Studio Amazing Views!

Rental unit in Plymouth

4.91 out of 5 average rating, 23 reviews

Luxury Two-Bedroom Penthouse with Roof Deck

Waterfront house rentals

Guest favourite

Home in Wareham

4.9 out of 5 average rating, 20 reviews

Waterfront Home in Onset for Happy Memories

Guest favourite

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

Guest favourite

Home in Falmouth

4.95 out of 5 average rating, 88 reviews

Private Waterfront Home on Picturesque Pond

Guest favourite

Home in Wareham

5 out of 5 average rating, 42 reviews

Peaceful waterfront home, large deck, 4 bedrooms

Guest favourite

Home in East Falmouth

4.9 out of 5 average rating, 60 reviews

Peaceful waterfront home with dock/ hot tub

Home in Brewster

4.82 out of 5 average rating, 164 reviews

Waterfront 4BR Home on Cape Cod

Guest favourite

Home in Hyannis Port

4.98 out of 5 average rating, 105 reviews

Beautiful Private Beach House

Waterfront condo rentals

Condo in Dennis Port

5 out of 5 average rating, 4 reviews

Cape Cod 1BR Condo on lovely Ocean Front Resort

Guest favourite

Condo in Dennis Port

4.92 out of 5 average rating, 26 reviews

Studio steps to a private beach!

Guest favourite

Condo in Plymouth

4.95 out of 5 average rating, 65 reviews

Lovely Suite w/ Balcony Overlooking Harbour!

Guest favourite

Condo in West Dennis

4.89 out of 5 average rating, 28 reviews

1BR 2nd Floor Condo with pool

Guest favourite

Condo in Chatham

4.86 out of 5 average rating, 88 reviews

Steps to Private Beach in Chatham

Guest favourite

Condo in West Dennis

4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

Guest favourite

Condo in Oak Bluffs

4.96 out of 5 average rating, 27 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Guest favourite

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
$196 CAD 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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