
Beachfront holiday rentals in Chatham
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Top-rated beachfront rentals in Chatham
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

SerenityViews | Lakefront | KingBed | Kayaks | FPL
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!

Little Boho Retreat by the Beach
Kick back and relax in the most calming, low charm country, coastal cottage the town of Marion has to offer. You’ll experience spectacular view of the beach right from the deck to watching the boats from the harbor. Don’t just limit yourself to life at the beach in just the summer months, come and make memories in this beautiful year-round cozy cottage. It's a perfect retreat to go swimming, kayaking, fishing, bird/seal/crabs watching and more right here in a private community on Dexter Beach.

WOW LAKE VIEW! Waterfront, Prvt Beach, King Bed!
Wake up to magnificent panoramic views of a beautiful lake with waves lapping below your window! See a video tour on YouTube: "WOW View! Cape Cod Lakefront Cottage. Private Beach, King bed" Guests love the stylish, peaceful, open design; wall-to-wall, floor-to-ceiling windows; private beach with picnic table and chaise lounge chairs; a full, modern kitchen; luxurious King gel/coil bed, private office, bathroom's curved shower, AC, and much more! It's like being on your own luxury houseboat!

Cape Cod Beachfront 2 bedroom Cottage Harwich
This adorable cottage is reflective of old Cape Cod and is part of a direct beachfront triplex property in the heart of Cape Cod with panoramic views of Pleasant Beach. Although you'll never feel like you need to leave the cottage because of its enviable location and views, it is close to the quaint Harwich village which boasts art and culture, restaurants and dining, shopping and family-friendly activities. This cottage is great for couples, families (with kids), and groups (up to 5).

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.

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!

Unique Waterfront Artist Cottage
Once a horse stable, Lil Rose now sleeps up to five just a short walk from a private beach. PLEASE READ BEFORE BOOKING: Rentals in season (April-October) are only offered by the week (Saturday-Saturday). November rentals are offered with a 4-night minimum. Rentals December-March are offered with a 3-night minimum. Pets are accepted (max 2) but you MUST let us know in your booking request about your pet so that we can prepare the property.

Modern Beachfront Condo, Great Views and Location!
Completely redecorated for 2023! This is the waterfront escape you have dreamed of! Awaken to sunrises over the bay while sipping your coffee, and in the evening, enjoy your cocktail and marvel at the ever changing colors of the sky, bay and boats as the sun slowly sets over your perfect Cape Cod day. This luxury beachfront condo is located in the heart of downtown and is just a couple of minutes walk from the ferry.

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.

Wings Neck Lighthouse
Once in a lifetime experience to stay in a Lighthouse. Historic, unique and charming but with all of the conveniences that make a great vacation. Just feet from the Atlantic with 360 degrees of ocean view. Beautiful, peaceful and memorable all year long. Sandy private association beach just steps away. Expansive lawn and patio for enjoying salt air, waves, boats and sunsets.

Ocean Edge Cape House with Beach, Pool, and AC
Your dream Cape Cod getaway awaits! This classic Cape Cod cottage is nestled in the heart of Brewster, offering a perfect blend of comfort, relaxation, and outdoor adventure. With access to a private beach, resort-style amenities, and iconic local attractions, this is the ultimate retreat for families, couples, or groups looking to experience the best of the Cape.

Gorgeous Sunsets! Private family beach!
Saturday to Saturday weekly rental during summer months. Wrap around deck, beach and waterfront. Open layout. Perfect for families & Couples with a family beach . Stunning sunsets, very private and close to Mashpee commons, Falmouth and New Seabury all 10 minutes away. We are happy to have you for stays longer than 7 days! Just send us a note!
Popular amenities for beachfront rentals in Chatham
Pet-friendly beachfront home rentals

Clear Pond Pet Friendly Inn

Bold Oceanfront Cottage w/Pvt Beach ~ Lil Sea Sass

Buzzards Bay - Beach Bungalow

On the water/Dog Friendly/Sleeps 7/SeaDuction

Oceanfront Home on Cape Cod Bay with Beach Access

The Front Cottage: Waterfront/Dock/Hot tub

Renovated West-end Condo on the Bay w/ Parking

Charming 2 Bed Steps to Falmouth Heights Beach
Beachfront home rentals with a pool

P-Town Beach Beauty on the Bay. Water View!

(Beachfront) 2BR/2BA Cottage w/ Front & Back Deck

Eco-Friendly Beach Home | Pool | 1-min walk to sea

ShoestringBayHouse, waterfront & pool in Cotuit

Beachside Villiage-Oceanfront

Bright Beach Condo • Walk to Sand & Shops

Condo in Falmouth MA

Beachfront Complex in Hyannis
Private beachfront home rentals

Steps to the Beach, Ocean View Dennisport Cottage

Waterfront Sunsets, Gateway to Cape Cod

Private Lake Beach | Spectacular Views & Amenities

Beachfront at Days' Cottages! Renovated, Kayaks!

Bay Dreams! Panoramic Bay Views!

Sunset on Shore - Lewis Bay Waterfront

LOCATION! Sea Captain's House, Walk to Beach/Town

Waterfront with Views & Kitchen-Preston Cross Hall
Quick stats about beachfront rentals in Chatham

Total holiday rentals
Explore 20 holiday rentals in Chatham

Nightly prices starting at
Chatham holiday rentals start at ₹9,662 per night before taxes and fees

Verified guest reviews
Over 850 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Chatham holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chatham rentals

4.7 Average rating
Chatham stays receive an average rating of 4.7 out of 5 from guests
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- Beachfront rentals Barnstable County
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- Cape Cod
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- White Horse Beach
- Coast Guard Beach
- Mayflower Beach
- Chapin Memorial Beach
- Pinehills Golf Club
- Nauset Beach
- Lighthouse Beach
- Town Neck Beach
- Inman Road Beach
- Ellis Landing Beach
- Nickerson State Park
- New Silver Beach
- Falmouth Beach
- Scusset Beach
- Cape Cod Inflatable Park
- Corn Hill Beach
- Cahoon Hollow Beach
- Kalmus Park Beach