Holiday rentals with a patio in Monterey

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Top-rated rentals with patio in Monterey

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Guest favourite

Cottage in Monterey, Massachusetts, US

5.0 out of 5 average rating, 18 reviews

Historic Berkshires Cottage with a View

Welcome to our beloved cottage, tucked into the hills of Monterey—one of the sweetest towns in the Berkshires—& just 5 minutes from Lake Garfield. Local legend has it that the house was an old hunting lodge, built by hand, and it still has all the quirks and charms that suggest that’s probably true. We’ve been slowly updating the cottage while carefully trying to retain its spirit, and we’ve put the renovation on hiatus to enjoy the place for the summer. Come visit our funky, enchanted hideout.

23–30 Oct

$465 SGD per night

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.

12–19 May

$453 SGD 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 :-)

8–15 Jun

$187 SGD per night

Guest favourite

Home in Otis

4.83 out of 5 average rating, 59 reviews

Springtime Oasis in the Berkshires!

Beautiful, centrally located home in Otis with seasonal water views of the reservoir! Just a few minutes drive from Otis ridge ski resort and the local lakeside beach for seasonal activities. This home is located next door to the only eat in Restaurant/Bar in town and even has a private trail that leads to this restaurant, Katies country store and boat Launch on the Otis reservoir! That same trail is also ride on snowmobile access for snowmobilers and enduro riders/mountain bikers and hikers.

3–10 Jun

$152 SGD per night

Guest favourite

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 103 reviews

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

27 Feb – 6 Mar

$314 SGD per night

Guest favourite

Flat in Hillsdale

4.96 out of 5 average rating, 74 reviews

Sweet Apt by Berkshires Catamount Walk to Brewery

Enjoy a stylish, elegant experience at this centrally-located newly restored 2 bedroom apartment with 1.5 baths in a historic building built in 1881, placed on the National Register of Historic places in 2010. Unit is on the 2nd floor and has a private entrance. Step back in time and stay in Second-Empire mansard Victorian that retains beautiful original details/layout and help it's restoration. Perfect location where the Hudson Valley meets the Berkshires. I have 4 other listings available.

29 Mar – 5 Apr

$178 SGD per night

Guest favourite

Cabin in Pine Plains, New York, US

4.98 out of 5 average rating, 174 reviews

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

15–22 Nov

$901 SGD per night

Guest favourite

Home in Great Barrington

5.0 out of 5 average rating, 67 reviews

Granite Ledge, Modern home in a unique setting

Welcome to Great Barrington, the heartbeat of the Berkshires! This newly remodeled home that sits on 3.5 acres, is conveniently located 1 min from Butternutt Ski Mountain, and a 6 min drive from downtown main street Great Barrington. Convenient to restaurants, shops, farmers markets, art galleries, Tanglewood, Stockbridge, The Norman Rockwell Museum, Simon’s Rock, etc. Enjoy a vibrantly diverse restaurant scene and cultural events while still staying in a private setting.

24–31 Dec

$716 SGD per night

Guest favourite

Treehouse in New Marlborough, Massachusetts, US

4.92 out of 5 average rating, 84 reviews

Double 3 Bedroom Tree House in the Berkshires

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

23 Feb – 2 Mar

$317 SGD per night

Guest favourite

Flat in Otis

4.98 out of 5 average rating, 60 reviews

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

17–24 Jul

$240 SGD per night

Superhost

Home in Monterey, Massachusetts, US

4.91 out of 5 average rating, 11 reviews

3bd Near Lake w Kayaks & Shared Tennis Court !

Relax and unwind at this beautifully put together 3bd home in the hidden gem of The Berkshires! This house is located in peaceful Monterey less than a miles walk from the lake. Relax and unwind on the lovely grounds, cook up some food for friends out on the back patio, or take a quick walk down to the town beach where a couple of kayaks will be waiting for you. Doesn't get much better than this home nestled right into the lakeside community that is Monterey.

8–15 Jun

$410 SGD per night

Guest favourite

Tiny home in Chatham

4.99 out of 5 average rating, 147 reviews

BLUSH: Boutique TINY home*private spa*walk to town

Cozy in at this PRIVATE OASIS & just steps from quintessential Main St. Indulgences abound in this one-of-a-kind curated space w/ lounge in upstairs loft & PLUSH queen bed tucked in its own nook. Perfect for a couple or girlfriends getaway. Fully equipped kitchen. Enjoy the convenience of village life with restaurants, brewery, shops, theater. Hike, explore town, soak in your PRIVATE HOT TUB, make s'mores at the firepit, or tuck in & cozy. @artparkhomes

25 Sep – 2 Oct

$346 SGD per night