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Vacation rentals in Tanglewood

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Popular amenities for Tanglewood vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Other great vacation rentals in Tanglewood

Guest favorite
A patio area features a stone fire ring surrounded by wooden Adirondack chairs. A red umbrella shades a dining table nearby, with additional seating areas visible. Lush green trees and shrubs provide a natural setting beside the barn's vibrant exterior.
Farm stay in New Lebanon
4.95 out of 5 average rating, 225 reviews

Barn Stay at Shadowbrook Farm

JenniferRating, 5 stars1 month ago
The space was beautiful, clean, and exactly as pictured! We enjoyed a weekend away and appreciated the local recommendations shared in the guide. We spent time exploring the farm, the surrounding area, and also were able to kick back and relax in the amazing property.
Guest favorite
A well-lit bathroom features blue floral accents on the shower curtain, complemented by a neutral tiled backdrop. Soft lighting is provided by an overhead light fixture with three bulbs. A pair of decorative towels is hung on a rail next to a white toilet, and artwork adorns the wall.
Apartment in Pittsfield
4.9 out of 5 average rating, 21 reviews

Green 2 bedroom Downtown

FabioRating, 5 stars2 weeks ago
I highly recommend the house.
Guest favorite
An evening view of a well-lit downtown area in Pittsfield, showcasing tree-lined streets, decorated with patriotic bunting. Cars are parked along the curbs, while shops display illuminated windows. A distant church steeple and hills are visible under the night sky.
Home in Pittsfield
4.95 out of 5 average rating, 20 reviews

Whispering Woods Guest House

James H, JrRating, 5 stars5 months ago
Taylor's space was exactly as described. Decorated so cute and extremely clean. Excellent amenities including well-appointed kitchen, snacks, coffee, tea, robes and slippers. Water pressure (including hot water) more than adequate. Tons of info available for "out of towners" if necessary. Communication was top notch.... accommodating, friendly and practically instantaneous. Would highly recommend. Thank you Taylor and Robert!!!
An inviting porch area is displayed, featuring a rustic wooden bench with neatly stacked firewood. Large windows allow natural light to fill the space, while a glimpse of the cozy interior with a fireplace and wooden ceiling is offered in the background.
Cabin in Monterey
4.87 out of 5 average rating, 235 reviews

Secluded cabin with babbling brook

CoriRating, 5 stars3 weeks ago
Truly a magical spot. We’ve stayed at many unique Airbnbs, and this one is up there as a favorite. It’s so peaceful and beautiful; the walk down makes it feel like you are truly remote and alone. The screened porch is perfect for listing to the stream at all points of the day. The cabin itself is furnished in a quirky and cozy way, and the beds are very comfortable. The full kitchen had everything needed. The host was super friendly and responsive. We would absolutely would recommend to others!
Guest favorite
The cozy living area features wooden walls and shelving filled with rustic decor. A large set of windows allows natural light to fill the space, casting shadows on the light-colored floor. A comfortable seating arrangement includes two armchairs and a coffee table, creating a welcoming atmosphere.
Guesthouse in Stockbridge
4.93 out of 5 average rating, 30 reviews

Light-filled Carpenter's Cottage in Stockbridge

EvaRating, 5 stars2 weeks ago
The house is very comfortable and feels like home. The kitchen is spacious and well-equipped — a great experience for cooking. There’s a peaceful courtyard that’s perfect for calming your mind or reading a book. One night, we even spotted a bear from the window! It’s a great location, and don’t worry — the bears are vegetarian. Elisa and Mickey are very kind and responsive. They’ll even create a personalized list to help you explore the town, even if you’re not familiar with the area. You can shop at Taft Farm — my favorite local farm. Cooking at the house really made it feel like home, and also “farm to table” experience. Thank you!
Top guest favorite
Cabin in West Stockbridge
5 out of 5 average rating, 7 reviews

Serene rustic mountain cabin in the Berkshires!

KellyRating, 5 stars2 weeks ago
Would love to come Back!
Guest favorite
The entrance features a sleek black door framed by natural wood paneling. A welcome mat lies at the threshold, inviting guests into a warm interior with wood flooring, visible through the open door. A glimpse of the cozy living space can be seen in the background.
Apartment in Great Barrington
4.96 out of 5 average rating, 84 reviews

King Bed|Berkshires|2m Ski Resort|Patio|Wi-Fi

SquireRating, 5 stars2 weeks ago
Great large room that is dog friendly and fairly priced. Not always easy to find! Bed was really comfortable. Weather was chilly and heat worked beautifully. Loved having a private little outdoor space too. Would definitely stay there again.
Top guest favorite
A modern cabin features a striking facade with large windows, surrounded by colorful trees. An outdoor deck contains multiple seating areas, including lounge chairs and a dining table. A wood-fired hot tub is situated nearby, surrounded by landscaped greenery and gravel pathways.
Cabin in East Nassau
5 out of 5 average rating, 45 reviews

Luxury Cabin | Breathtaking Views & Outdoor Fun

ElaineRating, 5 stars2 weeks ago
Matt and Sarah’s place is wonderful. A great place to relax and enjoy the beautiful surroundings. The house is just as described and the hosts make you feel right at home. We hope to come back again!
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