Search Holiday Homes in The Berkshires

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Check prices for these dates

Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul
In one month
1 Aug - 3 Aug
In two months
29 Aug - 31 Aug

Browse Select The Berkshires Holiday Homes

Deluxe Queen Room with 2 Queen Beds
Property grounds

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is £116
includes taxes & fees
7 Jul - 8 Jul
Deluxe Queen Room with 2 Queen Beds
Imagine Being Lakeside This Summer! Book Now!
Interior

Imagine Being Lakeside This Summer! Book Now!

10.0 out of 10, Exceptional, (16)
"Had a great trip. House was perfect for our group. Comfy beds, great fireplace and nice location near lots of local attractions."
Imagine Being Lakeside This Summer! Book Now!
4 Mi to Great Barrington: Berkshires Retreat!
Fridge, microwave, stovetop, dishwasher

4 Mi to Great Barrington: Berkshires Retreat!

10.0 out of 10, Exceptional, (1)
"Cozy little place with great space for dogs. The owner was responsive and ensured we had a lovely stay. "
4 Mi to Great Barrington: Berkshires Retreat!
Stay Lakeside This Summer!
Property grounds

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (73)
"Great location near town and on a pretty lake. Owners easy to deal with and very responsive. Our family had a great trip to the Berkshires!"
Stay Lakeside This Summer!
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (57)
"We had a wonderful time and loved the house! We will definitely be back!"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Rustic 3bd Lake Front Country Cottage
Smart TV, fireplace, stereo

Rustic 3bd Lake Front Country Cottage

9.4 out of 10, Exceptional, (3)
"Enjoy our hikes and lake front view as well as kayaking around lake. Pretty area."
Rustic 3bd Lake Front Country Cottage
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Garfield Townhouse in the Berkshires on Main St
Fridge, microwave, oven, stovetop

Garfield Townhouse in the Berkshires on Main St

10.0 out of 10, Exceptional, (12)
"Great location and comfortable."
Garfield Townhouse in the Berkshires on Main St
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (7)
"Delightful property, worked well for our needs"
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshire Lake at the Pillow, and EV!
Fridge, microwave, oven, stovetop

Berkshire Lake at the Pillow, and EV!

9.4 out of 10, Exceptional, (15)
"Had a lovely time at this lake house. The lake access was a plus and the house was well stocked with water accessories and food items. Otis is a short distance from Lee and Lenox providing easy Berkshire access. Having a garage to park the car in was also nice. The only downside is the relatively poor condition of the driveway / shared road the house is on. The neighborhood is made up of single lane dirt roads that have suffered from some wet weather. All in all would definitely recommend."
Berkshire Lake at the Pillow, and EV!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Dining

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (12)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.
Property grounds

Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

10.0 out of 10, Exceptional, (2)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
The price is £345
includes taxes & fees
16 Jul - 17 Jul
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
North Getaway Cottage
Exterior

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is £336
includes taxes & fees
2 Jul - 3 Jul
North Getaway Cottage
Great Barrington Lakeside Getaway w/ Kayak & Grill
Microwave, stovetop, dishwasher, toaster

Great Barrington Lakeside Getaway w/ Kayak & Grill

8.6 out of 10, Excellent, (9)
"The house was clean, comfortable, and had everything we needed. One of our best VRBO rentals to date! Will definitely stay here again."
Great Barrington Lakeside Getaway w/ Kayak & Grill
Water-View Home in the Berkshires
Outdoor dining

Water-View Home in the Berkshires

9.6 out of 10, Exceptional, (21)
"Nice house on a serene pond. Convenient location to all Berkshires attractions and NW CT."
Water-View Home in the Berkshires
Berkshires Retreat: Firepit, Grill, Screened Deck!
Exterior

Berkshires Retreat: Firepit, Grill, Screened Deck!

10.0 out of 10, Exceptional, (35)
"2nd time staying at this property. "
Berkshires Retreat: Firepit, Grill, Screened Deck!
Charming 3-bedroom farmhouse in Lenox
Terrace/patio

Charming 3-bedroom farmhouse in Lenox

Charming 3-bedroom farmhouse in Lenox
Secluded Family Home in Serene Stockbridge Woods
Dining

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (21)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
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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