Apartment holiday rentals in The Berkshires

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Popular amenities for The Berkshires apartment rentals

Weekly apartment rentals

Guest favourite
Apartment in Hunter
4.87 out of 5 average rating, 87 reviews

Cozy Gem with Mountain Views

AbishekRating, 5 stars2 weeks ago
Loved this place. Very easy to find. The place is cute and co portable with good views from the main bedroom and living room. Very clean and tidy. Loved the stay.
Guest favourite
Apartment in Dover
5 out of 5 average rating, 16 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

OferRating, 5 stars1 week ago
This place is so welcoming and tasteful. Lots of in-house activities for the evening, when it's raining, or just when you feel like staying in. An easy recommendation.
Guest favourite
Apartment in Waterford
4.92 out of 5 average rating, 36 reviews

Light Down at the Poet's Perch

StephanieRating, 5 stars1 month ago
This was our 2nd stay at Rhonda's place- felt like home again. As before, she was very helpful, thought of everything ahead of time, and was very quick to respond to all our questions. The flat is clean, cozy, and comfortable- hope to stay again sometime.
Superhost
Apartment in New Ashford
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

DanielRating, 5 stars3 months ago
Jiminy Peak is a great family mountain. Christina's place is perfectly located to do everything right out your back door. Christina was an excellent host. Thank you.
Superhost
Apartment in Adams
4.76 out of 5 average rating, 41 reviews

Downtown Adams Vintage Getaway

ChristyRating, 5 stars1 month ago
Ashley has a great place!! It was a fantastic place to visit with my friends and reminisce. Weirdly, this rental turns out to be the place my great grandparents lived and did business as my grandma grew up. I did not have any ghostly contact with my relatives in the apartment (I was kind of hoping and not hoping to see them šŸ˜‚), but I still had such a meaningful time sitting in the spaces they did so many years ago. Ashley is an excellent host and I will come here again next time I ā€œcome homeā€. 😊
Superhost
Apartment in Farmington
4.81 out of 5 average rating, 53 reviews

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

DenisRating, 5 stars6 months ago
Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!
Top guest favourite
Apartment in Dover
5 out of 5 average rating, 58 reviews

Four Seasons Slope-side Getaway at Mount Snow

AlexRating, 5 stars2 months ago
Dean and Tina are excellent hosts! We had a great weekend on the mountain. Their home is very comfortable and awesome location.
Top guest favourite
Apartment in Northampton
4.97 out of 5 average rating, 63 reviews

Lovely 1bedrom apartment with screened in porch

LauraRating, 5 stars3 weeks ago
Beautiful and very clean space! We had the most wonderful long weekend at Goran's apartment. He was so responsive and super friendly... cannot recommend enough. We will be back!

Pet-friendly apartment rentals

Guest favourite
Apartment in Litchfield County
4.95 out of 5 average rating, 21 reviews

Pacer's Pasture

CerayeRating, 5 stars5 months ago
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!
Top guest favourite
Apartment in Kerhonkson
5 out of 5 average rating, 24 reviews

Bright & Cozy | Walk to Rail Trail

FangRating, 5 stars2 weeks ago
Well designed, well maintained modern style home. Love the warm toned interior. Quick drive to lots of hiking spots which was what brought us here. Management team was very professional and easy to communicate. Will consider for any future trips to Minnewaska/Mohonk.
Guest favourite
Apartment in Stratton
4.94 out of 5 average rating, 103 reviews

Great 2 bedroom condo at Stratton Mountain

KatieRating, 5 stars3 months ago
Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!
Superhost
Apartment in Kingston
4.91 out of 5 average rating, 144 reviews

Cozy & walking distance to cafƩs *spring avails*

JananiRating, 5 stars2 months ago
Cozy apartment, walking distance from the water front. Had a great weekend getaway.
Guest favourite
Apartment in North Adams
4.96 out of 5 average rating, 74 reviews

Newly renovated 2BR on historic Eagle Street.

CaryRating, 5 stars1 week ago
Katie's place was great--very stylish, conveniently located, and well maintained/cleaned. Loved the renovation of the older building to create a contemporary space while incorporating some of the historic beams and brick work into the design. The living area and kitchen were spacious, comfortable, and well-appointed. The beds were very comfortable. It was great to have a dedicated parking space. The street is busy and well lit, so we were happy to have ear plugs and eye shades when trying to sleep. The location is convenient to MassMOCA and some great restaurants. All in all, a fantastic stay!
Guest favourite
Apartment in Hunter
4.95 out of 5 average rating, 61 reviews

Hunter Mountain 2BR Condo - Steps to Slopes!

KellyRating, 5 stars3 months ago
This is my second stay at Daniel’s, and it was just as good as the first! I love the location of his place in relation to the mountain. It’s a quick walk up the parking lot to the trails/lifts. Most importantly, my pups feel right at home, and they know his place now! His home is always clean and the linens/towels always smell fresh! I told him I will be coming back multiple times throughout the snow season to go boarding. He is very responsive and helpful and would go out of his way if need be! Overall, 12/10 recommend Daniel’s spot!
Superhost
Apartment in Windham
4.54 out of 5 average rating, 48 reviews

2. Beautiful, Cozy Condo with view of Windham Mtn

ShahibRating, 5 stars2 weeks ago
Sam was great host super responsive, clean space left us great recommendations to eat and visit.
Guest favourite
Apartment in Dover
4.85 out of 5 average rating, 169 reviews

Mount Snow Close, Great Price, Lots of Room

PeteRating, 5 stars2 months ago
Very close to Mount Snow. Walking distance to market, coffee house and Dover Bar and Grill. A dog friendly rental with everything you need for a ski trip.

Apartment rentals with a pool

Superhost
Apartment in Norwich
4.84 out of 5 average rating, 151 reviews

Villa Flora @ Norwich Inn & Spa

ChristianRating, 5 stars3 weeks ago
Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again
Guest favourite
Apartment in Hancock
4.95 out of 5 average rating, 58 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

EladRating, 5 stars1 month ago
A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful dĆ©cor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.
Guest favourite
Apartment in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars3 months ago
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.
Guest favourite
Apartment in Dover
4.91 out of 5 average rating, 110 reviews

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim

MichaelRating, 5 stars2 months ago
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.
Guest favourite
Apartment in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars1 month ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Guest favourite
Apartment in Stratton
4.95 out of 5 average rating, 148 reviews

Cozy condo within walking distance to the slopes.

MaraRating, 5 stars3 months ago
You really can’t beat this location. It’s across the steet from the lifts and the village with lots of restaurants/bars/stores. The space was perfect for our family of four. Our two young children stayed on the pullout and we thought the king bed was quite comfy. We would def stay here again!
Superhost
Apartment in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars15 months ago
We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!
Superhost
Apartment in Dover
4.8 out of 5 average rating, 110 reviews

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

BrendanRating, 5 stars2 months ago
Perfect location to mt snow.. right across the street. It's an older complex but had everything we needed for a few days of skiing.. would rent again

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