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Featured Apartments in The Berkshires and around

Lovely two bedroom river-view rental unit
Private kitchen

Lovely two bedroom river-view rental unit

9.2 out of 10, Wonderful, (19)
"Typical New England older home. 2nd floor unit. Comfy beds, well-stocked kitchen (that did remind me a bit of my first place out of college). This is definitely not The Ritz, but the linens were soft and the place worked for us."
The price is €312
includes taxes & fees
25 Nov - 26 Nov
Lovely two bedroom river-view rental unit
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Food and drink

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (8)
"Super cute, cozy and excellent location. Loved our stay. Will be back!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Park Street Penthouse Apartment
Games room

Park Street Penthouse Apartment

9.0 out of 10, Wonderful, (2)
"Like exploring new areas. Quaint town with a few restaurants and a diner in walking distance. Huge apt - well more than needed for one night … clean and has everything you would need to stay longer including laundry and full kitchen. Little hot bc only has window AC units as it’s an old art deco building. Close driving to my resorts and things to do in zbershired"
The price is €336
includes taxes & fees
24 Nov - 25 Nov
Park Street Penthouse Apartment
Charming Apartment In Berkshire Victorian Home
Interior

Charming Apartment In Berkshire Victorian Home

7.8 out of 10, Good, (7)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (20)
"We had a lovely time at this large and welcoming condo. It was easy to find, had all the amenities we needed and was just the perfect place for an off-season get away. Would easily re-book at any time during the year. "
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
2-Bdr Apt In Town, By the Water
Outdoor dining

2-Bdr Apt In Town, By the Water

9.4 out of 10, Exceptional, (3)
"Lovely property, in good shape. Close to many Williamstown attractions."
The price is €242
includes taxes & fees
24 Nov - 25 Nov
2-Bdr Apt In Town, By the Water
Private 1-bedroom apartment in enchanting North Adams with WiFi.
Exterior detail

Private 1-bedroom apartment in enchanting North Adams with WiFi.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Dianne was great and accommodating. Check in was so easy and the apartment was more spacious than expected! Very clean, neat, and organized. She made our stay at North Adams welcoming and would definitely book again. Thank you so much! "
The price is €247
includes taxes & fees
24 Nov - 25 Nov
Private 1-bedroom apartment in enchanting North Adams with WiFi.
Garfield House Studio at 208
Outdoor dining

Garfield House Studio at 208

9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Miscellaneous

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (60)
"Beautiful property with flower farm, pick your own berries and vegetable farm stand. Rustic log cabin feel with all amenities needed with kitchen."
The price is €211
includes taxes & fees
24 Nov - 25 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Private apartment in beautiful country barn
Fridge, microwave, oven, stovetop

Private apartment in beautiful country barn

10.0 out of 10, Exceptional, (18)
"Great farmhouse in the Berkshires. Location is out of the way without being out of the way. Communications with the host is great. Very accommodating."
Private apartment in beautiful country barn
New Studio In Town, By the Water
Property grounds

New Studio In Town, By the Water

10.0 out of 10, Exceptional, (3)
"Great location"
The price is €230
includes taxes & fees
24 Nov - 25 Nov
New Studio In Town, By the Water
Vacation Rental Home in the Berkshires!
Outdoor dining

Vacation Rental Home in the Berkshires!

9.6 out of 10, Exceptional, (10)
"Beautiful property, amazing views, lots of privacy, home is nicely decorated and had everything we needed and more. Will definitely visit again!"
Vacation Rental Home in the Berkshires!
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Property grounds

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

9.2 out of 10, Wonderful, (9)
"Such a awesome facility! Love the room, the Jiminy property is very cool and you don’t even need to leave to go anywhere else because there is so much to do here. Stay."
The price is €222
includes taxes & fees
24 Nov - 25 Nov
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Main Street Delight 1bedroom
TV

Main Street Delight 1bedroom

10.0 out of 10, Exceptional, (18)
"The location was fantastic for our stay in the Berkshires. Walkable to many restaurants & shops. It was very well decorated & cozy. Very convenient being above a coffee shop, however not ideal if you enjoy sleeping in. We could hear the consistent squeaking of the coffee shop door as soon as it opened in the morning (~7:00 am) from the bedroom. However, good motivation to get up and enjoy the beautiful Berkshires!"
Main Street Delight 1bedroom
Heart of Lenox!! - renovated downtown apartment
Flat-screen TV

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (63)
"The bathroom was less than tidy and when I recall it was like that last time. Bathroom rug is dirty or just dirty looking. I advise property Meg to buy several Along with a Terry bath mat so you can cover it when using. No little extras like soap/shampoo are offered. I had My own. Overall the apartment is very cute would stay again. "
Heart of Lenox!! - renovated downtown apartment
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Exterior

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

9.6 out of 10, Exceptional, (29)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
The price is €222
includes taxes & fees
24 Nov - 25 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Vacation Rental Home in the Berkshires!
Outdoor dining

Vacation Rental Home in the Berkshires!

3.0 star property
Vacation Rental Home in the Berkshires!
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Property grounds

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

10.0 out of 10, Exceptional, (2)
"Stayed one night at one of my favorite ski spots. Will be back again!"
The price is €222
includes taxes & fees
24 Nov - 25 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Baldwin Hill Retreat Guest House
Fridge, microwave, oven, stovetop

Baldwin Hill Retreat Guest House

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property and neighborhood were gorgeous! Walkable roads with low speed limits and a nearby park were major bonuses. Plenty of food options nearby, and downtown Great Barrington is only a short drive away. The house was super clean, gorgeously furnished, and very cozy. The beds and linens were very good quality and I had an incredibly restful stay. I will certainly be renting this spot for my next trip to the area! "
Baldwin Hill Retreat Guest House
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
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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Other property types in The Berkshires

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is €186
includes taxes & fees
24 Nov - 25 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is €157
includes taxes & fees
24 Nov - 25 Nov
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
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.