Holiday rentals with a patio in Lee

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Top-rated rentals with patio in Lee

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.

7–14 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 :-)

21–28 Oct

$183 SGD per night

Guest favourite

Home in Otis

4.83 out of 5 average rating, 60 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.

19–26 Jun

$160 SGD per night

Superhost

Home in Lee

4.86 out of 5 average rating, 7 reviews

River Front Cottage

Our cozy river front home with lovely mountain view that will make your next stay in the Berkshires a memorable one! Located in the heart of the Southern Berkshires, this home is a 3 minute drive to downtown Stockbridge, 5 to Lee Outlets. When you're not enjoying the beautiful backyard view, venture just 10-15 minutes to Berkshire favorites including: Tanglewood; Divine Mercy Shrine; Norman Rockwell Museum; Shakespeare & Company; Edith Wharton's The Mount; hiking; skiing; and outdoors galore!

11–18 May

$286 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

22–29 Jan

$223 SGD 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.

26 Mar – 2 Apr

$94 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.

22–29 Aug

$239 SGD per night

Superhost

Home in Lee

4.93 out of 5 average rating, 30 reviews

Midcentury Meets Modern on Goose Pond

Winter on Goose Pond is magical. 1000 feet above Lee in a thick forest is a microclimate with more snow - frequently coating the trees for a winter wonderland. You'll feel nice and cozy inside curled up next to one of two fireplaces watching the snow fall on the lit outdoor decks. Seven downhill or cross country ski areas within a short drive, ice fishing, snowmobiling, and ice skating all round out what has been called one of America's best Christmas towns.

15–22 Sep

$695 SGD 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!

4–11 Nov

$154 SGD per night

Guest favourite

Home in Lee

4.97 out of 5 average rating, 70 reviews

Stylish Mid-century Modern Berkshires Cape

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. 15 minutes from Butternut ski to south + Bousquet to the north, 35 min to Jiminy Peak. Cozy up by the wood burning fireplace (firewood provided) and enjoy the winter wonderland! The house is decorated in mid century modern style with gorgeous design touches throughout!

16–23 May

$515 SGD per night

Guest favourite

Tiny home in Chatham

4.99 out of 5 average rating, 273 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 Jul

$354 SGD per night

Guest favourite

Cottage in Monterey

5.0 out of 5 average rating, 34 reviews

Beaver Lodge

Come and enjoy total relaxation on 4 acres with a beaver pond, a meadow and forest. Feel like in a resort with a hammock, outdoor patio! All in the Berkshires, close to Tanglewood, Lake Garfield, Ski Butternut. The eco friendly house offers 3 bedrooms, the main on the first floor, one and a half bathrooms, a fully equipped kitchen, outdoor dining area, wood burning fireplace, electric car charger.

18–25 Mar

$287 SGD per night