Holiday rentals with a patio in Pittsfield

Find and book unique rentals with patio on Airbnb

Top-rated rentals with patio in Pittsfield

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

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Guest favourite

Home in Becket

4.93 out of 5 average rating, 118 reviews

Lake front retreat - Stylish Berkshire home

Drive down a lovely country wooded road to this renovated 4 bedroom mid century home on Long Bow Lake. The house has wood floors throughout & hip design. Gas fireplace in the dining room. This will be a home for the family to enjoy. We have our own private lake frontage that includes a dock & 4 kayaks. Enjoy the screened in porch, Weber gas grill, ping pong table & games. The area is quiet & peaceful only 20 minutes from Downtown Lee, Outlets, fabulous hikes & minutes from skiing Otis Ridge.

9–16 Dec

₹29,390 per night

Guest favourite

Guest suite in Great Barrington

5.0 out of 5 average rating, 45 reviews

Sweet 1-bedroom with salt water pool

Welcome to our home in the beautiful Berkshires! Enjoy this clean, private downstairs apartment with your own entrance. We are just 10-min from downtown Great Barrington and in a wonderful location for exploring. Upstairs is my family- a 6 year old boy and medium-sized dog- you will hear us! Sometimes we have friends and family visiting. In the summer you may see us at the pool with them. We’re happy to meet you and also happy to give you space- it’s your call. Wishing you a wonderful trip :-)

10–17 Sep

₹12,149 per night

Guest favourite

Flat in Lanesborough

5.0 out of 5 average rating, 22 reviews

Cozy Berkshire Waterfront Home

Welcome to our charming waterfront home on Pontoosuc Lake! The Berkshire Lakescape is perfect for a romantic getaway for a couple or two, or a solo adventure away. Soak in lake views from the deck or try to catch a stunning sunset from the water’s edge. Kayak straight from our backyard and return for marshmallows at the firepit. Explore Berkshires' culture and outdoor activities - Tanglewood, Mount Greylock, and more are just a short drive away. We can't wait to host you for a memorable stay.

1–8 Jun

₹17,050 per night

Guest favourite

Tiny home in Catskill

4.93 out of 5 average rating, 133 reviews

Venster- Your window to wilderness

Two hours from NYC, close to skiing (hunter mountain/ Windham, Kaaterskill falls, Woodstock, Hudson, Saugerties. Book us and make Hudson Getaways your base station for all kinds of adventures. Enjoy facilities of a bigger house in a tiny form factor. Heat/AC, Queen bed, Hot shower, Kitchenette, cooktop, Fridge, Towels, linens, soap, coffee etc. *Hudson Getaways is a small woman owned business. We offer discounts to our social media followers, to returning guests and during slow seasons.

24 Sep – 1 Oct

₹12,373 per night

Guest favourite

Home in Pittsfield

4.94 out of 5 average rating, 100 reviews

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grant piano. Musicians are welcome!

18–25 Oct

₹20,803 per night

Superhost

Flat in Pittsfield

4.86 out of 5 average rating, 42 reviews

The Sunset Sanctuary - King Bed with Kitchen

Welcome to our cozy 1-bedroom apartment with a charming front porch and a private entrance with ample parking! Nestled in a peaceful neighborhood, this inviting retreat is the perfect place for a relaxing getaway or a romantic escape. The house is located just opposite of the Cumberland gas station where you can get breakfast, snacks, drinks or coffee along with any essentials. It’s only 3 mins drive from the Berkshire Medical Center and 20 mins drive from Tanglewood.

16–23 Nov

₹5,728 per night

Guest favourite

Flat in Adams

4.88 out of 5 average rating, 58 reviews

Mountain Living, 1-bedroom unit, outdoor hot-tub

Relax & enjoy nature in this tranquil, 1 bedroom unit down the block from Mt. Greylock, highest mountain in MA! 2 minutes away from hiking trails, 10 minutes away from Mass Moca, 25 minutes away from Jiminy Peak ski resort. Enjoy MT Views, and jump in the outdoor jacuzzi right outside your bedroom. WiFi, AC, your own thermostat & TV. The suite you’ll be staying in is directly attached but separate access from the main house. Military and HCP discounts

3–10 Aug

₹7,998 per night

Guest favourite

Flat in Hudson

4.95 out of 5 average rating, 100 reviews

Restored 19th century farm house apartment

Brought back from the original bnb boarding days of the 19th century is our 1 bedroom top floor apartment located on a peaceful country road 15 minutes from downtown Hudson or Red Hook. You can still see the original numbers of the old boarding house on the doors! The house is surrounded by 12 acres of fields and forest that we welcome you to explore. It’s a small homestead with animals, a geo dome greenhouse and garden. Hope you enjoy!

11–18 Jun

₹11,812 per night

Guest favourite

Tiny home in Chatham

4.99 out of 5 average rating, 274 reviews

Sugar Shack - 300 square feet of pure sweetness.

A very PRIVATE OASIS yet steps from quintessential Main Street lined with restaurants, brewery, shops, theater. A blissful & sweet retreat only 2.5 hrs from NYC & Boston. This custom space (tiny home+hot tub+she-shed) provides the utmost privacy and is thoughtfully designed with indulgence in mind. Hike, explore town, soak in your private hot tub, make s'mores at the firepit, or tuck in & cozy. @artparkhomes

8–15 Oct

₹21,679 per night

Guest favourite

Apartment in Hudson

4.94 out of 5 average rating, 142 reviews

Harmony Valley Home, bright & inviting 2-BR escape

You and your guests will be close to it all when you stay at our centrally-located home. The space is nestled perfectly between the Berkshire and Catskill Mountains, which provides countless opportunities for adventure! Whether a romantic getaway or a family vacation- you are an idea away from an unforgetable experience! Wineries breweries Musuems Hiking trails Empire State Rail Trail Conservation Areas

23–30 Dec

₹12,018 per night

Guest favourite

Flat in Enfield

4.99 out of 5 average rating, 143 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

22–29 Apr

₹7,177 per night

Guest favourite

Guest house in Williamstown

4.97 out of 5 average rating, 146 reviews

Brookside Cottage

Drift off to the sound of a babbling brook outside the bay window in this cozy country cottage. Minutes from Downtown Williamstown, North Adams and Bennington, VT. We are about 20 minutes away from Jiminy Peak for downhill skiing. The trails behind our house are ideal for snowshoeing, nordic skiing, and snowman building.

12–19 Aug

₹11,243 per night