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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

4.96 out of 5 average rating, 123 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.

Home

4.88 out of 5 average rating, 193 reviews

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

Guest favourite

Tiny home

4.98 out of 5 average rating, 283 reviews

Writer's Cabin in Woods near Wellfleet Bay

Our unique, creative and magical "Writer's Cabin" tiny house is a guest favorite! You'll be tucked in the woods with the views of a treehouse, and just minutes' drive or bike ride to Wellfleet's beaches, ponds & walking trails. Wellfleet's quaint town center and harbor are just a 10-15 minutes walk down the road. Note: the cabin has a private, wooden Nordic shower w/ hot water built onto the outside of the cabin. Our guests love this unique experience! The toilet is standard flushing & indoors.

Guest favourite

Home

4.95 out of 5 average rating, 264 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

Cottage

4.94 out of 5 average rating, 334 reviews

Newly renovated Cape Coddage! Location! Location!

Newly renovated! Harwichport home- 2 min walk to beach, sleeps 10. Located right by Bank St Beach In Harwichport! Walk 1-2 minutes to the beach or walk 1-2 minutes in the other direction to Main Street where you will find shops and restaurants. Ember, The Port, 3 Monkeys, Beer Garden, and Mad Minnow. This home is in the dream location. Pull in and you don't need to drive until you leave. Walkable to Wychmere beach club. This home is often shared by guests of events celebrated at Wychmere.

Guest favourite

Guest suite

4.99 out of 5 average rating, 591 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

Rental unit

4.97 out of 5 average rating, 260 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.

Home

4.97 out of 5 average rating, 103 reviews

Chatham Charm

Welcome to our newly renovated 4-bed, 2-bath Cape house close to downtown Chatham and beaches! The house is equipped with central air, wifi, a living room TV with cable, smart TVs in 3 bedrooms, and a washer/dryer set. The property also includes a large deck and back yard, great for grilling and outdoor activities. We have a property manager nearby to help with any needs you may have during your stay. Sat-Sat 7-night minimum stay last 2 weeks of June through end of August.

Guest favourite

Cottage

4.94 out of 5 average rating, 162 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

4.93 out of 5 average rating, 266 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

4.92 out of 5 average rating, 173 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

Apartment

4.86 out of 5 average rating, 88 reviews

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.

Holiday rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for outdoor seating rentals in Chatham

Free parking on premises

Air conditioning

House rentals with outdoor seating

Guest favourite

Home

5 out of 5 average rating, 124 reviews

Family Friendly Cozy Retreat w/ Fireplaces & Sauna

Guest favourite

Home

4.99 out of 5 average rating, 329 reviews

Fabulous Waterfront! 3bdrm/2bth Kayaks & Firepit

Home

4.95 out of 5 average rating, 100 reviews

Violet’s Place- king bed- hot tub!

Guest favourite

Home

5 out of 5 average rating, 205 reviews

Harwich Retreat on Cape Cod - Relax or explore!

Guest favourite

Home

5 out of 5 average rating, 16 reviews

Chatham is an amazing place to be in the fall!

Guest favourite

Home

5 out of 5 average rating, 15 reviews

Chatham Vibes

Guest favourite

Home

5 out of 5 average rating, 6 reviews

Happy Yellow House near Beach

Guest favourite

Home

4.86 out of 5 average rating, 139 reviews

Cozy and easy to beach & downtown

Apartment rentals with outdoor seating

Guest favourite

Rental unit

4.93 out of 5 average rating, 180 reviews

King bed/Hot Tub/Waterfront-The Lotus

Guest favourite

Rental unit

4.91 out of 5 average rating, 247 reviews

Eastham Escape

Rental unit

4.89 out of 5 average rating, 105 reviews

Peaceful retreat in the woods...

Guest favourite

Rental unit

4.92 out of 5 average rating, 132 reviews

Walk to private beach, spacious peaceful apartment

Guest favourite

Rental unit

4.97 out of 5 average rating, 195 reviews

Sunny Studio Apartment on Martha's Vineyard

Guest favourite

Rental unit

5 out of 5 average rating, 102 reviews

Stylish retreat | walk to town | fire pit

Guest favourite

Rental unit

4.95 out of 5 average rating, 288 reviews

Cozy Waterfront Apartment, Private Beach Access

Guest favourite

Rental unit

4.83 out of 5 average rating, 109 reviews

A quiet, private, unique spot in a great location!

Apartment rentals with outdoor seating

Guest favourite

Apartment

5 out of 5 average rating, 31 reviews

Condo on Lighthouse Beach in Chatham

Guest favourite

Apartment

4.97 out of 5 average rating, 177 reviews

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

Guest favourite

Apartment

4.94 out of 5 average rating, 49 reviews

Two bedroom condo close to beach

Apartment

4.86 out of 5 average rating, 81 reviews

Walk to beach! Chatham Luxury near downtown, CBI!

Guest favourite

Apartment

4.96 out of 5 average rating, 28 reviews

Lovely two-bedroom condo in Brewster MA!

Guest favourite

Apartment

4.96 out of 5 average rating, 49 reviews

Door to shore in a hop, skip, and a jump!

Guest favourite

Apartment

4.91 out of 5 average rating, 23 reviews

.02 to the beach/fall in love @ THE LOVE SHACK

Guest favourite

Apartment

4.88 out of 5 average rating, 123 reviews

A Spectacular. Walk to beach, town and harbor 20

Quick stats about holiday rentals with outdoor seating in Chatham

Total rentals
230 properties
Nightly prices starting at
€ 57 before taxes and fees
Total number of reviews
9K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
10 properties have a pool

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