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Holiday rentals with outdoor seating in Chatham

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Chatham

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Home in Chatham

4.96 out of 5 average rating, 120 reviews

Summerfell Cottage close 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.

Guest favourite

Guest suite in Chatham

4.99 out of 5 average rating, 219 reviews

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table just steps to a fresh water pond & outdoor shower. The friendly, cottage-style decor is inviting w/queen-size bed, couch, ample closets, private bathroom w/shower, small dining area w/microwave & fridge (no stove, no bbq); writing table, WiFi, Roku & DVD player. Enjoy the water view! Minutes by car to downtown Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

Guest favourite

Home in Chatham

4.95 out of 5 average rating, 253 reviews

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.

Guest favourite

Guest suite in East Harwich

4.99 out of 5 average rating, 564 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Nine 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.

Guest favourite

Guest suite in Chatham

4.99 out of 5 average rating, 112 reviews

Spacious Moonhouse Studio - Chatham

Spacious studio apartment located above attached garage, with separate entrance and a relaxing private outdoor space. Perfect retreat for 1-2 people. Property is quietly situated off of a private road. Located one half mile from Ridgevale Beach along Nantucket Sound, also including nearby bike trail access. Short drive to Schoolhouse Pond, three miles from downtown Chatham. Three miles from popular Chatham Bars Inn and the Wychmere Beach Club Generally, a three night minimum.

Guest favourite

Rental unit in Chatham

4.96 out of 5 average rating, 244 reviews

The Knoll

A quiet home nestled next to conservation land. You will be greeted by a big friendly white dog, hear the gentle water fall of a small pond. 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.

Guest favourite

Home in Chatham

4.96 out of 5 average rating, 114 reviews

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.

Guest favourite

Cottage in Chatham

4.94 out of 5 average rating, 152 reviews

Cape Cod Classic Cottage Near Forest Beach

See Cape Cod at its most traditional in this cozy, fully renovated cottage. Get a good night's sleep in the cozy bedrooms with central a/c and blackout shades. Prepare for the day in the clean and bright interior. Pack up your beach chairs and cooler and take a short walk down to Forest Beach. Grab your bike and hop on the Cape Cod Rail trail nearby or take a short drive into charming downtown Chatham. After a day in the sun, unwind in the hammock or enjoy a BBQ on the deck.

Guest favourite

Guest suite in Brewster

4.93 out of 5 average rating, 169 reviews

Cozy and Secluded Apartment/Seasonal garden view

Walk across your private patio through sliding glass doors to your private garden retreat in this spacious studio. A large bathroom is just off the kitchen. This brand new apartment is designed for your perfect vacation or retreat from city life. If you are working from home - try working from Cape Cod! A desk awaits you - leave your computer set up and ready! Not the best apartment for disabilities - the entrance is in the back and there is a step up into the shower.

Guest favourite

Guest suite in West Harwich

4.93 out of 5 average rating, 242 reviews

Cape Hideaway

Private suite on the first floor guests have exclusive use of the entire place. The second floor is my residence. The suite has a bedroom with queen temperpedic mattress, living room with queen sleep sofa, small kitchenette and bath. The kitchen is equipped with a small refrigerator, microwave, coffee maker, kettle, single burner cooktop and crockpot. Guests have access to the upper deck (shared space) which has a patio set and gas grill.

Guest favourite

Guest suite in East Orleans

4.92 out of 5 average rating, 153 reviews

Charming Old Cape Cod

Relax and enjoy spending time at Snowtop on the Town Cove, many activities including sailing, paddle boarding, water skiing and spectacular sunsets! A short walk to swim, sit on the sand or take a beach walk. The offered space has a private entrance with bath, bedroom with a king size bed, a sunny living room with dining table over looking the water where you could choose to dine in, have coffee in the morning or play a game.

Guest favourite

Guest suite in Orleans

4.99 out of 5 average rating, 214 reviews

Private Beach, Cozy Cape Cottage

Enjoy your own private beach with soaring seabirds and ocean breeze! Let a breathtaking sunrise and view of the bay greet you every morning from bed. Take in the waterfront view on the outside patio by the garden or in the enclosed sun porch. Escape to our cozy cottage secluded in the woods with nearby trails. Explore the Cape's many attractions and refresh your soul with a relaxing Cape Cod vacation.

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Popular amenities for outdoor seating rentals in Chatham

Free parking on premises

Air conditioning

House rentals with outdoor seating

Guest favourite

Home in West Dennis

4.92 out of 5 average rating, 100 reviews

Adorable Cottage - Premier Location in West Dennis

Guest favourite

Home in Yarmouth Port

4.99 out of 5 average rating, 319 reviews

Fabulous Waterfront! 3bdrm/2bth Kayaks & Firepit

Guest favourite

Home in Harwich Port

5 out of 5 average rating, 193 reviews

Harwich Retreat on Cape Cod - Relax or explore!

Guest favourite

Home in Brewster

4.94 out of 5 average rating, 112 reviews

Shop, Swim, Hike, Bike in Historic Brewster

Guest favourite

Home in Harwich

4.93 out of 5 average rating, 134 reviews

Sea Inspired: A Cape Cod Escape-Harwich/Chatham

Guest favourite

Home in Yarmouth

5 out of 5 average rating, 113 reviews

Guest Favorite Cape House | Sauna & Bar Shed

Home in Brewster

4.88 out of 5 average rating, 180 reviews

Water Front Pond House - 3 acre Cape Cod Sanctuary

Guest favourite

Home in Chatham

5 out of 5 average rating, 20 reviews

The Chatham Bars White Foam House Steps From Beach

Apartment rentals with outdoor seating

Guest favourite

Rental unit in East Orleans

4.94 out of 5 average rating, 270 reviews

Cozy Waterfront Apartment, Private Beach Access

Guest favourite

Rental unit in East Harwich

4.9 out of 5 average rating, 272 reviews

The Secret Garden

Guest favourite

Rental unit in South Orleans

4.92 out of 5 average rating, 126 reviews

Walk to private beach, spacious peaceful apartment

Guest favourite

Rental unit in North Falmouth

4.95 out of 5 average rating, 253 reviews

Upscale suite w/ separate entrance.

Guest favourite

Rental unit in Brewster

4.95 out of 5 average rating, 151 reviews

Sophisticated, Private Cape Cod living

Guest favourite

Rental unit in North Eastham

4.9 out of 5 average rating, 220 reviews

Eastham Escape

Guest favourite

Rental unit in North Eastham

4.93 out of 5 average rating, 160 reviews

Little Pearl

Guest favourite

Rental unit in East Dennis

4.86 out of 5 average rating, 147 reviews

Peace By The Bay

Apartment rentals with outdoor seating

Guest favourite

Apartment in New Seabury

4.97 out of 5 average rating, 115 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Guest favourite

Apartment in Dennis Port

4.94 out of 5 average rating, 127 reviews

Charming Condo, Short Walk to Beach

Guest favourite

Apartment in Provincetown

4.95 out of 5 average rating, 168 reviews

Bayshore 9 Waterfront Renovated Condo with Parking

Guest favourite

Apartment in Provincetown

5 out of 5 average rating, 122 reviews

Prime Location | King Bed | Sunset Views | Parking

Guest favourite

Apartment in Brewster

4.98 out of 5 average rating, 166 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

Guest favourite

Apartment in Provincetown

4.91 out of 5 average rating, 179 reviews

West End Cozy, Bright and Airy!

Guest favourite

Apartment in Provincetown

4.92 out of 5 average rating, 291 reviews

Beachfront Town Center

Guest favourite

Apartment in Provincetown

4.93 out of 5 average rating, 121 reviews

Westend Waterfront Luxury Condo-Provincetown

Quick stats about holiday rentals with outdoor seating in Chatham

Total rentals
220 properties
Nightly prices starting at
$81 SGD before taxes and fees
Total number of reviews
7.8K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
130 properties have a dedicated workspace

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