Holiday rentals with a patio in Egremont

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Top-rated rentals with patio in Egremont

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

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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

$194 SGD per night

Guest favourite

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 104 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.

4–11 Mar

$307 SGD per night

Guest favourite

Flat in Hillsdale

4.96 out of 5 average rating, 75 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.

8–15 Dec

$174 SGD per night

Guest favourite

Home in Copake

4.92 out of 5 average rating, 39 reviews

Yellow Door House

Stay at our casual, pet friendly property in the beautiful Hudson Valley. Vaulted ceiling great room opens into the kitchen & sunroom, with 2 cozy bedrooms rounding out the space. The yard is extensive with a deck & fire pit, backing up to a wooded area. Nearby Robinson Pond offers swimming & kayaking. While dogs aren’t allowed on the beach, they will love the quiet walkable roads. Hudson NY, Great Barrington MA, Bash Bish Falls, Harlem Valley Rail Trail & Catamount are all within 30 minutes

11–18 Jun

$153 SGD per night

Guest favourite

Home in Great Barrington

4.93 out of 5 average rating, 75 reviews

Best of the Berkshires + Hot Tub by Evergreen Home

Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 15 minutes to the slopes or 7 minutes to downtown Great Barrington, this stylish, cozy rental has everything you need for a great getaway. A new renovation brings modern amenities to this classic 50’s cottage. Enjoy a chef’s kitchen, 500 sq-foot deck with hot tub, and thoughtful touches like yoga mats, a record player, board games, and a backyard hammock. Monthly ski rental discounts available!

2–9 Oct

$418 SGD per night

Guest favourite

Flat in Great Barrington

5.0 out of 5 average rating, 15 reviews

King Bed | Stylish | Wi-Fi | *2m Ski Resort*

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

26 Jan – 2 Feb

$199 SGD 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

$198 SGD per night

Guest favourite

Guest house in Great Barrington

4.96 out of 5 average rating, 50 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

1–8 Jun

$250 SGD per night

Guest favourite

Cabin in Pine Plains, New York, US

4.98 out of 5 average rating, 176 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

4–11 Dec

$772 SGD per night

Guest favourite

Bungalow in Egremont

4.99 out of 5 average rating, 67 reviews

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

14–21 May

$471 SGD per night

Guest favourite

Home in Egremont

4.93 out of 5 average rating, 55 reviews

Modern and Stylish Country Lakeside Cottage

Direct view of and use of waterfront. One king bedroom, one bath, cook's kitchen with high end appliances. Banquette seating surrounded by banks of windows. Large living room with gas fireplace. Small loft area above living room with queen bed. Cathedral ceilings. Large bath en suite. Washer/Dryer. Patio and fire pit for marshmallows. Boat/swim in summer or ice fish/skate in winter. A perfect spot to enjoy the outdoors. Stone’s throw from Catamount and Butternut.

1–8 Jun

$376 SGD per night

Guest favourite

Home in Hillsdale

5.0 out of 5 average rating, 23 reviews

Enjoy all 4 Seasons

Newly renovated, a mix of country and modern furnishings. Bright, sunny and airy feel. Located on 1 acre with a beautiful sun-soaked deck. Easy access to Hillsdale, Rail Trails, 20 minutes to Hudson, Great Barrington, Catamount Ski & Adventure Park. Sleeps 6 comfortably, 2-bdr, 1 large bath, spacious living and dining. Kitchen with lots of natural light and deck access. Relax on hammock, swing in a tire, or sit by the fire. Washer and dryer available for use.

21–28 Jul

$269 SGD per night