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Top Holiday Rentals in West Stockbridge

Pool
Wellspring by AvantStay | Indoor Pool + Views
10.0 out of 10, Exceptional, (2)
"We had the whole family come together to stay for the weekend and celebrated two birthdays while relaxing at the peaceful property. The pool was the main focus of our stay!!"
Wellspring by AvantStay | Indoor Pool + Views
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1672)
"Very nice spot quiet "
The price is £155
per night
2 May - 3 May
Vacation Village in the Berkshires
2 Bedroom Condo 1/2 mile from base | Private kitchen | Microwave, stovetop, coffee/tea maker, toaster
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (856)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is £130
per night
7 May - 8 May
Jiminy Peak Mountain Resort
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7 bedrooms, iron/ironing board, cots/infant beds, travel cot
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (28)
"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (181)
"Thank you, Justin, for sharing your beautiful home with my family. We had a very nice time and relaxed in the beautiful quiet surroundings. I was so excited when I saw some Norwex items as I am a consultant and also use Norwex in my home. We hope to visit again in the warmer months as it was a perfect memory for our family. Thanks again, The Short family"
Peace and quiet on the lake
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (194)
"The house is beautifully remodeled and clean. Nice open area with all like new kitchen appliances. My friend and I are thinking of going back in the summer to enjoy the lake"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Fridge, microwave, oven, stovetop
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Balcony
Micosta Leisure Inn
3.0 star property
8.8 out of 10, Excellent, (70)
"I needed a place to sleep while attending several events in the area and this was perfect; clean, safe, warm, great snacks. The only negative was the icy steps and deck. I had to break up the ice and clear with my boots. Place could use an electric kettle for tea. Other than that it was a great place for me and my elderly dog. "
The price is £112
per night
2 May - 3 May
Micosta Leisure Inn
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (202)
"The property was quiet and clean."
Berkshire Village Carriage House - Super Private!!
TV, fireplace, DVD player, books
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Fridge, microwave, oven, stovetop
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Lake
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
9.8 out of 10, Exceptional, (10)
"It was unique, with unusual amenities, like the home theater and fabulous game room. Our weather was wintery, so this was such a comfortable and fun way for the family to spend time together!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (10)
"The hosts have made this ranch house into an artsy, cozy place for families to rest and relax! Plenty of space for family hang outs and game playing, but also enough rooms for tweens or teens to get away and have alone time. Beautiful spaces throughout. We would have loved to enjoy the backyard space and screened-in porch if it hadn't been winter, but appreciated watching the snow falling while sipping coffee by the kitchen window! Close to Catamount ski area and minutes from Stockbridge shops...
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Beautiful, Private Estate w/ Pool, Pond, Rec Room, Gym, Library, Barn, Trails!
9.6 out of 10, Exceptional, (79)
"We had 4 families and grandparents all stay together for an unforgettable weekend at Bellavista. The house had enough space for us to hang out together playing charades in the great room, ping pong tournaments in the finished attic playroom, and making holiday ornaments at the large dining room table. There were also spaces to have quiet moments when you needed it...and we even enjoyed a beautiful hike at a nearby conservation area that Laurie recommended. The house was extremely clean, fully...
Beautiful, Private Estate w/ Pool, Pond, Rec Room, Gym, Library, Barn, Trails!
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"The house was perfect and Sydney was a great host. "
Quintessential 6-BR Berkshires Lodge
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See all available properties in West Stockbridge
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.

Other types of properties in West Stockbridge you may be interested in

Garden view
Pleasant Valley Motel West Stockbridge
2.0 star property
6.8 out of 10, (902)
" Great stay for the price "
The price is £62
per night
6 May - 7 May
Pleasant Valley Motel West Stockbridge
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (380)
"This is a lovely place to say. Very warm and welcoming. The staff was very helpful and even brought a little doggy basket for my dog. It included a blanket, dog bowls treats and more!! Had a very very nice time. "
The price is £113
per night
3 May - 4 May
Shaker Mill Inn
Lobby
Life House Berkshires
3.5 star property
9.2 out of 10, Wonderful, (231)
"Very accommodating and friendly staff. Coffee in the morning was excellent. "
The price is £88
per night
6 May - 7 May
Life House Berkshires
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.

Everything you need to know about West Stockbridge holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the West Stockbridge holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect West Stockbridge holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

West Stockbridge holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West Stockbridge. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A West Stockbridge holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of West Stockbridge holiday rentals we have selected for you start as low as £112 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on West Stockbridge rentals

At Expedia, we put the best West Stockbridge holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top West Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream West Stockbridge holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around West Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in West Stockbridge?

Yes, there are holiday rentals in West Stockbridge close to Berkshire Botanical Garden, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to West Stockbridge speak positively about the gardens and restaurants in this destination. Make sure you have time to check out the forests and lake views during your trip.

What are some of the best holiday rentals that West Stockbridge has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of West Stockbridge is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in West Stockbridge?

With 24 Expedia holiday rentals, you're guaranteed to find just the right place for your West Stockbridge stay.

What can I see and do in West Stockbridge?

Family-friendly attractions include Charles H. Baldwin & Sons and Hotchkiss Mobile Studio, whereas Berkshire Botanical Garden is a spot to enjoy the outdoors. While here, Chesterwood and Ebenezer II Gifts and Antiques are other places worth a visit.

What are holiday rentals like in West Stockbridge?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in West Stockbridge. Holiday rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family getaway.

Recent reviews of West Stockbridge properties
Expedia verified reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

5/5 Excellent
"The staff are awesome! "
A verified traveller stayed at Best Western Plus Berkshire Hills Inn & Suites
Posted 1 day ago
Best Western Plus Berkshire Hills Inn & Suites