
Vacation rentals with a patio in Berkshire County
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Top-rated patio rentals in Berkshire County
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Apartment rentals with a patio

Mountainside Condo Ski on/off
A great place for a skiing getaway at Jiminy Peek Resort! Ski - in, ski -out, a lovely appointed condo, with access to a hot tub. Frank was most helpful and friendly. I highly recommend his place.

Lavishly Appointed 2BR Apt. Home
A charming place and cozy stay! Robert was responsive and friendly. Also, I highly recommend the shrimp and cheddar grits at District Bar & Kitchen which is only a few minutes away. So good!

Historic Victorian - Entire 3rd floor
Spacious stay, wonderfully clean and quiet and an excellent view from the balcony. Lots to see and do in the area. It got a bit cold in the bedroom at night - advise packing some warm pajamas if traveling in the colder seasons!

Guestrooms on the Bike Trail
My stay at Yina's was perfect for what I was looking for. The space was cozy and quiet and that bed was so comfortable. There was a nice work space with a refrigerator as well which was convenient. Yina and Katelynn were quick to respond to messages etc.

Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
We had a great stay!! It was the perfect spot for an overnight. We loved the area and especially appreciated their recommendations! Hopefully next time we can stay longer and see even more!

"Nostalgia" a spacious2 bedroom first floor unit.
I have booked Sandy's place several times and will continue to do so! Very happy with everything!

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT
Very happy with our stay at Frank’s in North Adams. Super friendly host and perfect place to enjoy a mixed bag of weather, mostly decent for early April, easy and content to both go out to see the city and just stay in to hang out in the three season porch or watch a movie. Great recommendations from our host for outdoor places to check out. Walkable. Peaceful. Would hope to stay here again

Downtown Jewel | Stylish | Fully Stocked | Firepit
Dalit’s downstairs unit at 208 Water Street is fantastic! Recently renovated with a fresh and stylish vibe. Location was perfect for us during our recent visit, and Dalit kept in great contact through a patch of tough winter weather. We appreciated the amenities set out for us and our dog. Thank you for a great stay!
House rentals with a patio

The Waffles House-cozy 4br w/hot tub, central loc
Very cute spot it's everything you need for a nice weekend. Love that it is dog friendly. The hot tub was perfect for the snowy weekend. Anne communicated really well. There were blankets for snuggling. We skied at Jiminy Peak, about 25 minutes away. This was conveniently located and close to restaurants and amenities.

Sun Filled Lenox Retreat - Minutes to Tanglewood!
This is one of our favorite Airbnb properties. This was our second visit and everything was great. Great amenities, great location, and great communication. We ended up being there during a lot of snow and difficult weather and Bespoke management took great care of things. We love the area, close to restaurants and skiing. Looking forward to visiting again.

Net Zero home with rustic Berkshire charm
Great, clean place with extra towels in the closet! Backyard was nice for our dog.

Marie’s Place unit 3
Marie's place was wonderfully charming and very clean. We appreciated the extra details that added to our stay. There were games, puzzles, and books for when we had free time. We appreciated that everything we needed to prepare a simple meal was in the kitchen, and that bathroom supplies were well stocked. The neighborhood was quiet and friendly, with children playing and people going for walks. Our family enjoyed our stay, and we hope to visit again soon!

Cascades Cottage | Stylish Tudor on Gorgeous St.
we had a great time staying here for a weekend. it was right by the trailhead and a very short drive to both the MoCa and Clarke. but most of all, we loved to simply hang out by the fireplace and listen to music on their record player. It was the perfect weekend getaway

Central Haus (Group getaway on a quiet street)
Great stay at Mian and Anthony's place. Kitchen was well stocked with everything we needed, there was tons of space, and comfy beds. We are grateful that they allowed us an early check in too. Would stay with them again gladly!

Lux on the River near Tanglewood w/220v EV charge
My friend and I had a lovely two-night stay at Julie's place. The house is the perfect retreat—peaceful, cozy, and beautifully located. We especially enjoyed the evenings by the wood-burning stove and long, leisurely breakfasts on the porch while listening to the river. The beds were incredibly comfortable, with high-quality pillows and bedding—we both slept so well! I would definitely love to come back someday with my husband to enjoy the peace and quiet, as well as everything else the Berkshires has to offer. Thank you, Julie and Arthur, for sharing your wonderful home with us!

Gregory Art House
We had a wonderful stay at Anna's place! It was our favorite of the three places we stayed in Massachusetts -- so comfortable but also interesting and charming, which can be a hard combination to pull off. The house had everything we needed for our stay and the hosts also left some lovely extra touches that made us feel so welcome as guests. The area is so lovely that we hope to have the chance to come back someday when the leaves are out and would definitely choose to stay here again if it's available!
Condo rentals with a patio

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
We had a wonderful stay at the condo - ideally located, spacious and comfortable and had everything we needed ! Definitely will be back! Elisabeth was generous, responsive and super friendly and excited for us for our trip!

Spacious 3 bedroom apt in Lenox historic downtown
Beautiful apartment with lots of rooms-comfy sitting areas and lots of light. It was very nicely appointed and the checkin was simple. We will definitely be back as the location is ideal.

Unique - Country suite @ Jiminy Peak
We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+

Downtown Adams Vintage Getaway
As described and walkable to local coffee houses and rail trail with Mass Moca a 10 minute drive away. The host was very communicative and helpful with clear directions inside the unit.

All-season Berkshires ski resort condo - Sitzmark
We spent a nice, early March ski weekend at this place - got lucky with the skiing and found the place ideal for our needs. Were traveling with a pet and the location was perfect from her perspective as well.
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Six Flags New England
- Taconic State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Opus 40
- John Boyd Thacher State Park
- Mount Greylock Ski Club
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Beartown State Forest
- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
- Bright Nights at Forest Park
- Rockledge Golf Club
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