Search Vacation Homes in The Berkshires

Compare 267 Vacation Homes in The Berkshires with updated reviews, rates, and availability.

Private Lake House in the Berkshires
Pool
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, (15)
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Hearts Desire is a furnished whole house in a small, colorful garden center.
Terrace/patio
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (66)
"Probably one of the cleanest places I have ever stayed. The house is perfect. Beautiful views!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Interior
Peaceful Retreat Compound 10 Minutes to Great Barrington!
10.0 out of 10, Exceptional, (11)
"The property was fabulous and had lots of activities on site(basketball hoops,pickleball court and pool). Excellent location close to Great Barrington downtown which has an amazing selection of restaurants. Overall,fantastic stay!"
The price is $800
$1,340 total
includes taxes & fees
Jun 10 - Jun 11
Peaceful Retreat Compound 10 Minutes to Great Barrington!
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Tranquil 3-BR Waterfront Retreat
Exterior
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, (7)
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Property grounds
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, (3)
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Golf
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (93)
"Everything is basic but solid and comfortable. Beds were nice and firm, my preference. Host was lovely. Wish we could have stayed longer to explore the area more."
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Waterview Home in the Berkshires: Near Hiking
Outdoor dining
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, (14)
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Private Cabin On Over 12 Acres Of Woods!
Fridge, microwave, oven, stovetop
Private Cabin On Over 12 Acres Of Woods!
10.0 out of 10, Exceptional, (3)
"The cabin is cozy and absolutely beautiful. We had everything we needed for a a relaxing stay in The Berkshires. Thanks for the comfort and welcoming hospitality."
The price is $824
$1,419 total
includes taxes & fees
Jul 6 - Jul 7
Private Cabin On Over 12 Acres Of Woods!
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
10.0 out of 10, Exceptional, (3)
"Our family had the pleasure of staying at this home during our child’s graduation from the nearby Berkshire school. It was the perfect situation for us in an idyllic setting very close to the campus. The home is over 250 years old and has been lovingly updated. The kitchen has seemingly all new appliances and gorgeous wood plank countertops with an adjacent windowed sitting area with a large hearth. The old and new are beautifully combined. Our family members spent a lot of time looking at the...
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
Berkshire Manor for Lasting Memories
Fridge, microwave, oven, stovetop
Berkshire Manor for Lasting Memories
10.0 out of 10, Exceptional, (2)
"Leah was a wonderful host to us. She provided easy-to-follow instructions for getting into the house, offered good suggestions on things to do and where to eat. Although the house was a bit larger than we needed, we chose it because of the location, the generous sized and comfortable looking (from photos) casual spaces, the kitchen and the number of bathrooms so we each had our own. This house did not disappoint! It has lots of New England charm, the beds were comfortable, as were the several...
Berkshire Manor for Lasting Memories
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Smart TV
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
The price is $360
$765 total
includes taxes & fees
Jun 10 - Jun 11
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (185)
"It was exactly as stated... Peace and quiet on the lake! With all the amenities, Beautiful backyard, Fire pit, Kayaks and canoes, Beautiful backdeck. Just an all around nice place to stay and relax."
Peace and quiet on the lake
Private Estate, Heated YEARROUND Outdoor Pool
Fridge, microwave, oven, stovetop
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
Fox Hollow Luxury Ranch Laurel Lake
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
The Meadows House @ Otis Ridge w/ 7-person hot tub
Property grounds
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Quintessential 6-BR Berkshires Lodge
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (12)
"we all loved it, especially the screened in porch...& my dog cooper also gives 5 stars"
Stockbridge Home, Come Experience The Berkshires!
Peaceful, Post and Beam Loft, Sleeps 9
TV, DVD player
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Chic Pittsfield Home With A View!
Property grounds
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Antique Farmhouse Totally Restored
Exterior
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (80)
"We have 20 years experience renting homes for family gatherings and this is the most interesting and amazing property. Gardens galore, plenty of space to congregate or go off by yourself, fully appointed kitchen, and comfortable space. We were a party of ten and everyone loved the experience."
Antique Farmhouse Totally Restored
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See all available properties in The 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.

Other property types in The Berkshires

Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (859)
"Great amenities and very clean property. Hot tub facilities and timings were also good. Just wished they had offered bath robes. "
The price is $148
$163 total
includes taxes & fees
Jun 18 - Jun 19
Jiminy Peak Mountain Resort
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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.

The Berkshires Vacation Homes information

Number of reviews
515
Accommodation
267 Vacation Homes
Lowest Price
$360
Highest Price
$824

Recent reviews of The Berkshires hotels
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"We are just stopping overnight, and feel we got lucky. This is a lovely small hotel on a lake with great views, boats to rent, and an excellent restaurant. It would be great for a vacation. "
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 2 days ago
The Black Swan Lee - Lenox, Ascend Hotel Collection