
Holiday rentals with outdoor seating in Chatham
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Top-rated rentals with outdoor seating in Chatham
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Walk to Ridgevale Beach
We have done extensive renovation and remodeling to the home with attention to detail. We believe we have created a warm and inviting atomosphere. The home is decorated in a coastal style with carefully chosen accents from the edison bulbs in the dining area to the custom barn/boathouse style door and repurposed hand hewn 18th century beam that anchors the staircase. The Kitchen is equipped with the same attention to detail for those who enjoy preparing their own meals. Summerfell is an entire home rental. Both hosts live nearby, Patty and Bill will be accessible via cell, text and email. The property is in a peaceful neighborhood with a good mix of seasonal homes and full time residences. The area has a number of quiet roads perfect for evening strolls. Of course, the beach is a short 5 minute walk away. The kitchen is equipped for the guest who enjoys cooking. From small appliances (Crockpot, waffle iron, blender, hand mixer etc) to small gadgets (citrus press, microplane, garlic press, potato ricer etc) A three burner weber gas grill is on the deck.

Spacious Modern Cottage, beach& Wychmere <1.4mile
Entire spacious newly renovated modern cottage in Harwich Port. Sun filled open concept living room with a large kitchen island. Great for families ! Less than 4 min drive to Red River beach and Bank street Beach. 3 min drive to Wychmere Beach Club wedding venue. Close to Harwich Port downtown. Centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy a hike to Harwich Thompson's field Conservation area. Close to bike trail

Cute cottage - walking distance to Ridgevale Beach
Retreat to this very quiet and peaceful residential shore neighbored on a dead end street. If LOCATION is what you're looking for, look no further! This year round cottage will serve as a comfortable and relaxing home away from home for your vacation, with walking rights to Ridgevale Beach about 300 yards from the front door. Provided in your home away from home vacation house are linens, towels, fully equipped kitchen, spacious out door shower, 2 roomy bedrooms, & 4 season porch to relax on.

Relaxing Retreat | King Beds * Sauna * Bar Shed
Welcome to Cape Away, your charming family & pet-friendly retreat! Enjoy a fully stocked kitchen, cozy fireplaces, sauna, and outdoor shower. Unwind with dozens of board games, dart board, fire pit, and BBQ. The fully fenced private backyard offers beach gear, a bar shed and lounge area. We are perfectly located just 5–20 minutes from top rated restaurants and beaches, making it your ideal home base. With premium amenities, thoughtful touches it’s the perfect space to escape, explore and relax.

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.

Romantic getaway suite
GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

The Knoll
A quiet home nestled next to conservation land at the end of a dirt road. Though there are neighbors, the landscaping creates a private oasis. The downstairs apartment with private entrance is old New England with Cape Cod affects. The Bedroom has a queen bed. Second sleeping area has a Daybed with trundle and is partially open to the living area. Outside deck has a grill and shower for guest use. Close to School House pond, bike path, and 3 miles from beaches, shopping, and downtown.

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.

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.

*Oceanfront Beach Home*
Steps to the beach for your morning walks. The sound of waves lulling you to sleep. A place for family and friends to relax and create memories. Nestled in the dunes of East Sandwich beach sits this oceanfront property (bay side) with stunning 360-degree views of Cape Cod Bay and Scorton Creek. Spend your days sunning and swimming before you return home to this comfortably appointed house. Also check out our new sister property down the road @ApresSeaCapeCod

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

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.
Popular amenities for outdoor seating rentals in Chatham
House rentals with outdoor seating

Harwich Haven: Pool & Fire Pit

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Quintessential Waterfront Historic Cottage

Walk to Downtown Chatham, Steps to Beach!

Amazing Location! Chatham Center, Walk to Beach!

Fabulous Waterfront with Spectacular Sunset Views!

Luxury 4 BR 1780s Cape, Near Wychmere, 3 King Beds

Gorgeous Home 1 mi to Beach, by Cape Cod Bikepath
Apartment rentals with outdoor seating

Songbird Studio- Secluded but close to everything!

Walk to private beach, spacious peaceful apartment

Sunny Studio Apartment on Martha's Vineyard

Rock on Wellfleet!

Cozy Waterfront Apartment, Private Beach Access

Apartment suite|Firepit|Private Deck|Pond Access

Upscale suite w/ separate entrance.

Beach Plum Apt w/Private Deck & BnB Hot Tub Access
Apartment rentals with outdoor seating

Modern Provincetown Condo.

Bayshore11 Waterfront Renovated Condo with parking

Stunning. Walk to Beach, Town and Harbor 113B

Modern Beachfront Condo, Great Views and Location!

Westend one bedroom condo

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth

Bayshore 9 Waterfront Renovated Condo with Parking

Charming Condo, Short Walk to Beach
Quick stats about holiday rentals with outdoor seating in Chatham
Total rentals
320 properties
Nightly prices starting at
$78 SGD before taxes and fees
Total number of reviews
11K reviews
Family-friendly rentals
300 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
20 properties have a pool
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- Cape Cod
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- Sea Street Beach - East Dennis
- White Horse Beach
- Coast Guard Beach
- Chapin Memorial Beach
- Pinehills Golf Club
- Nauset Beach
- Lighthouse Beach
- Inman Road Beach
- Town Neck Beach
- Ellis Landing Beach
- New Silver Beach
- Nickerson State Park
- Falmouth Beach
- Cape Cod Inflatable Park
- Scusset Beach
- Cahoon Hollow Beach
- Kalmus Park Beach
- Forest Beach