West Stockbridge Holiday Rentals
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Our top choices for West Stockbridge holiday rentals
1. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
9.0 out of 10, Wonderful, (1,271 reviews)
"Excellent stay!!!!"
Susan J
The price is NZ$195
includes taxes & fees
6 Dec - 7 Dec
2. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
Ofer C.
The price is NZ$1,080
includes taxes & fees
16 Nov - 17 Nov
3. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
8.8 out of 10, Excellent, (2,850 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
Carol
The price is NZ$182
includes taxes & fees
15 Nov - 16 Nov
4. Sweet Cozy Victorian in Housatonic. Close to everything.
Sweet Cozy Victorian in Housatonic. Close to everything.Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
Eric H.
The price is NZ$544
includes taxes & fees
15 Nov - 16 Nov
5. Cozy 1-bedroom studio in serene Great Barrington with AC
Cozy 1-bedroom studio in serene Great Barrington with ACGreat Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
bob i.
The price is NZ$209
includes taxes & fees
25 Nov - 26 Nov
6. Micosta Leisure Inn
Micosta Leisure InnHudson
9.2 out of 10, Wonderful, (197 reviews)
"Great stay"
George
The price is NZ$167
includes taxes & fees
19 Nov - 20 Nov
7. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
Joanna P.
The price is NZ$354
includes taxes & fees
16 Nov - 17 Nov
8. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
Leslie H.
The price is NZ$380
includes taxes & fees
15 Nov - 16 Nov
9. A Cozy Berkshire Escape l Close to the Slopes
A Cozy Berkshire Escape l Close to the SlopesGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
Kelly B.
The price is NZ$539
includes taxes & fees
16 Nov - 17 Nov
10. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga CenterLenox
The price is NZ$542
includes taxes & fees
11 Dec - 12 Dec
11. Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
Patricia O.
The price is NZ$1,077
includes taxes & fees
15 Nov - 16 Nov
12. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is NZ$2,234
includes taxes & fees
30 Nov - 1 Dec
13. Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Walk into town, soak up sun on enclosed porch & steps away from nature trails!Stockbridge
10.0 out of 10, Exceptional, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
Anonymous traveller
The price is NZ$1,463
includes taxes & fees
7 Dec - 8 Dec
14. Luxury Barn Near Hudson With New Private Sauna
Luxury Barn Near Hudson With New Private SaunaEast Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
Michael T.
15. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, LakeGreat Barrington
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
Kristin O.
The price is NZ$586
includes taxes & fees
16 Nov - 17 Nov
16. 1789 Shaker Farmhouse in Berkshires/Hudson Valley
1789 Shaker Farmhouse in Berkshires/Hudson ValleyCanaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
Christine C.
The price is NZ$720
includes taxes & fees
18 Nov - 19 Nov
17. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
Janet G.
The price is NZ$542
includes taxes & fees
13 Dec - 14 Dec
18. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness roomGreat Barrington
10.0 out of 10, Exceptional, (10 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
Roberta
The price is NZ$2,145
includes taxes & fees
20 Nov - 21 Nov
19. Berkshires Apartment at the Stephentown Hotel
Berkshires Apartment at the Stephentown HotelStephentown
10.0 out of 10, Exceptional, (6 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
Nicole O.
The price is NZ$375
includes taxes & fees
15 Nov - 16 Nov
20. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/DryerGreat Barrington
The price is NZ$665
includes taxes & fees
20 Nov - 21 Nov
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top West Stockbridge Hotel Reviews
The Red Lion Inn
10/10 Excellent
Find out more about West Stockbridge
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our West Stockbridge holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up West Stockbridge. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in West Stockbridge. Seeing all the best attractions is bound to make you fall in love with West Stockbridge. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in West Stockbridge short-term rentals, that won’t be hard to do.
