Search Vacation Homes in The Berkshires

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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Vacation Homes in The Berkshires

Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

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 isnā€™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 ā€œokā€ and hung up. Thankfully there was...
The price is SARĀ 446
SARĀ 582 total
includes taxes & fees
18 Jun - 19 Jun
Deluxe Queen Room with 2 Queen Beds
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.
Smart TV, fireplace, video games, DVD player

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. "
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

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

9.4 out of 10, Exceptional, (10)
"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!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (121)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House
Contemporary Berkshire Home with Views of Taconic Golf Course
Smart TV, fireplace, DVD player, books

Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Aerial view

Sun Filled Lenox Retreat - Minutes to Tanglewood!

The price is SARĀ 758
SARĀ 1,797 total
includes taxes & fees
19 Jun - 20 Jun
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Becket Home w/ 3-Season Porch: Walk to Lake Access
Fridge, microwave, oven, stovetop

Becket Home w/ 3-Season Porch: Walk to Lake Access

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a clean, quiet spot for a nice weekend getaway. "
Becket Home w/ 3-Season Porch: Walk to Lake Access
Luxury Vacation Rental in the Berkshires!
Outdoor dining

Luxury Vacation Rental in the Berkshires!

10.0 out of 10, Exceptional, (14)
"Stayed here multiple times and will come back again. Great place to stayā€¦"
Luxury Vacation Rental in the Berkshires!
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (20)
"The property was close to town and very cozy, clean & comfortable. Would highly recommend attention to the details was impressive."
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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!
Stay Lakeside This Summer!
Exterior

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (72)
"Perfect location for a peaceful, scenic vacation."
Stay Lakeside This Summer!
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (13)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
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)
"Perfect location and accommodation for my family. The home was as described. I would recommend it. The property owner was easy to work with. "
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
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)
"Comfortable and relaxing spot. Really pretty lake. Fun stuff for paddling around the lake."
Berkshire Lake at the Pillow, and EV!
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (12)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
4 Mi to Great Barrington: Berkshires Retreat!
Fridge, microwave, stovetop, dishwasher

4 Mi to Great Barrington: Berkshires Retreat!

4 Mi to Great Barrington: Berkshires Retreat!
4Br/3bath Lakefront House in Berkshires. June week now available. Hi speed wifi
Exterior

4Br/3bath Lakefront House in Berkshires. June week now available. Hi speed wifi

10.0 out of 10, Exceptional, (152)
"Hi,The views are spectacular, house is spacious and close to skiing. We had a great time staying in this house. We even talked about coming back in warmer weather. "
4Br/3bath Lakefront House in Berkshires. June week now available. Hi speed wifi
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Fridge, microwave, oven, stovetop

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

10.0 out of 10, Exceptional, (34)
"Our family had a wonderful stay at this beautiful home. It's well-equipped, clean and cozy and feels like you are out in the country but also a 10 minute drive from great restaurants, shops and skiing. We definitely plan to return."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
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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