Holiday rentals with a patio in Lanesborough

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Top-rated rentals with patio in Lanesborough

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Guest favourite

Home in Lanesborough

4.92 out of 5 average rating, 25 reviews

Historic Stone Church in The Berkshires

Hinterland Hall was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay. Follow us @hinterlandhall Please inquire about weddings & events.

31 Aug – 7 Sep

$484 SGD 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.

22–29 Oct

$332 SGD per night

Guest favourite

Place to stay in North Adams

4.93 out of 5 average rating, 115 reviews

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

30 Aug – 6 Sep

$907 SGD per night

Guest favourite

Home in Lanesborough

4.95 out of 5 average rating, 19 reviews

Chic Berkshire Retreat by Evergreen Home

Feel like you have entered your own oasis in this charming retreat. A hidden gem set far back from the road, tucked away on almost 3 acres of privacy with lush nature This 3 BR, 1.5 bath home seamlessly blends modern updates with mid-century decor, and features a brand new spacious deck to relax and take in the unobstructed mountain views. Centrally located; 6 minutes to Mt Greylock, 4 minutes to Cheshire Lake and the Ashuwillticock Rail Trail, 12 minutes to adventure at Jiminy Peak.

19–26 Oct

$358 SGD per night

Guest favourite

Home in Adams

4.91 out of 5 average rating, 69 reviews

Mountain View Hideaway

Welcome to the Hideaway! This 800sqft home is located on a small hill with a beautiful direct view of Mount Greylock. This amazing home is perfect for anyone who's looking to explore the Berkshires by day and come back to a tranquil home by evening. This small but mighty house has a full kitchen, very comfortable lounging couch, quiet bedroom with an adjacent office area, full bathroom with a washer and dryer and a front and back yard. Everyone is welcomed to enjoy this gem of a home!

18–25 Feb

$161 SGD per night

Superhost

Cabin in Lanesborough

4.83 out of 5 average rating, 53 reviews

Cozy stream-side cabin

Nestled in the heart of the Berkshires along a cool, fresh-water stream. This 1-bedroom 650 sq. ft. bungalow has been completely renovated and ready to welcome you. It is conveniently located to many area attractions and is situated near the base of Mount Greylock, the highest peak in Massachusetts. The main living space has a working brick fireplace, cathedral ceilings, recessed lighting, a French door, real pine wood walls, and a loft that overlooks the main living space.

28 May – 4 Jun

$250 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.

22–29 Mar

$93 SGD per night

Guest favourite

Tiny home in Chatham

4.99 out of 5 average rating, 151 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

10–17 Jul

$343 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!

3–10 Feb

$140 SGD per night

Guest favourite

Home in Lanesborough

5.0 out of 5 average rating, 88 reviews

Tranquil mid-century modern Berkshires retreat

We love the Scandi House because of its simplicity, openness, warmth, comfort, trees, space, privacy, and convenience. We enjoy this Berkshires retreat for its close proximity to all what Berkshires has to offer in music, arts, and outdoor activities. Most of all, we treasure the tranquility and each other when we are here at the house in the woods.

29 May – 5 Jun

$514 SGD 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

$182 SGD per night

Guest favourite

Cottage in Lanesborough

4.98 out of 5 average rating, 46 reviews

Amazing 2 bedroom lake front cottage, large patio

Looking for a relaxing weekend alone or with friends and family? This peaceful lake front property will make you feel like you will never want to leave. Whether you want to fish, have a cookout, watch the sunset, or even boat watch from the dock, this secluded cottage is the right spot for a calm weekend getaway.

4–11 Jun

$572 SGD per night