Top Resorts in The Berkshires
Find the Top Resorts in The Berkshires – 30+ Quality Options from Leading Providers
1-20 out of 35 resorts
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8.6
Great6969 reviews10
From
US$ 740
/night
- Luxurious spa offering unique holistic treatments
- Elegant New England-inspired dining experiences
- Picturesque gardens and scenic countryside views
Resort
8.2
Great6060 reviews10
From
US$ 189
/night
- Ski-in/ski-out access to Jiminy Peak
- Outdoor heated pool for year-round use
- On-site adventure park attractions
Hotel
8.4
Great131131 reviews10
- Outdoor Pool
- On-site Spa
- Dining Room
From
US$ 140
/night
- Historic charm dating back to 1773
- Pet-friendly policies welcomed by guests
- Live music at The Lion's Den bar
Bed & Breakfast
8.4
Great3232 reviews10
- Heated Pool
- Outdoor Fireplace
- On-site Spa
From
US$ 261
/night
- Chef-prepared breakfast with seasonal ingredients
- Historic Victorian charm with modern comforts
- Cozy rooms with fireplaces for winter stays
8.4
Great312312 reviews10
- Indoor Pool
- Outdoor Hot Tub
- Game Room
From
US$ 135
/night
- Stunning views of Jiminy Peak ski area
- Heated indoor and outdoor swimming pools
- Family activities and entertainment options
Hotel
8.4
Great3636 reviews10
- Fitness Center
- Full-service Restaurant
- Outdoor Firepit
From
US$ 299
/night
- Seasonally inspired, locally sourced cuisine
- Flexible indoor-outdoor event space
- Pet-friendly accommodations with treats
8.4
Great7373 reviews10
- Indoor Pools
- Mini Golf
- Activity Center
From
US$ 347
/night
- Multiple indoor and outdoor pools
- Family-friendly activities and entertainment
- Fully equipped kitchen in accommodations
Bed & Breakfast
8.4
Great6565 reviews10
- Family Rooms
- Private Bathroom
- Air Conditioning
From
US$ 200
/night
- Free parking for all guests
- Family-friendly accommodations available
- Pet-friendly policy welcomed here
Inn
8.8
Great3636 reviews10
- Fine Dining
- Luxury Suites
- Historic Charm
From
US$ 483
/night
- Historic inn built in 1806
- Locally sourced dining prepared by Chef Paul Pearson
- Luxurious rooms with Carrara marble bathrooms
Hotel
9.2
Perfect6666 reviews10
- Heated pool
- Tennis court
- Jacuzzi
From
US$ 395
/night
- Seasonal outdoor swimming pool
- On-site spa and wellness centre
- Restaurant with vegan options
Bed & Breakfast
8.4
Great5757 reviews10
- Gourmet Breakfast
- Historic Tours
- Charming Common Areas
From
US$ 171
/night
- Historical charm with famous past guests
- Chef-crafted gourmet breakfast daily
- Themed rooms reflecting local history
Inn
8.2
Great2222 reviews10
- On-site Spa
- Dog-Friendly Rooms
- Event Hosting
From
US$ 614
/night
- Hästens handmade luxury mattresses
- Artfully designed themed guest rooms
- Homemade gourmet breakfast included
Resort
8.4
Great8686 reviews10
- Indoor pool
- Tennis courts
- Game room
From
US$ 167
/night
- Indoor and outdoor pools available
- Tennis courts and hot tub onsite
- Game room with billiards and movies
Motel
8.2
Great100100 reviews10
- Garden Views
- Complimentary Breakfast
- Country Decor
From
US$ 124
/night
- Country-style decor with garden views
- Complimentary breakfast served in gardens
- Affordable stays for children under 14
Motel
8.6
Great119119 reviews10
- Heated Pool
- Picnic Area
- Tennis Court
From
US$ 59
/night
- Ski package for Jiminy Peak tickets
- Heated pool for summer relaxation
- Delightful decor and comfortable rooms
Inn
8.4
Great8080 reviews10
- Skiing
- Free Parking
- Air Conditioning
From
US$ 99
/night
- On-site skiing for adventure seekers
- 24-hour security for guest safety
- Express check-in and check-out service
8.4
Great7474 reviews10
- Fitness centre
- Skiing
- Private porches
From
US$ 195
/night
- Gourmet breakfast changes daily
- Historic Victorian mansion ambiance
- Complimentary afternoon snacks available
Motel
8.2
Great8989 reviews10
- Ski storage
- Cozy Garden
- Children's playground
From
US$ 148
/night
- Ski storage and waxing area available
- On-site Cozy Garden Restaurant serves American food
- Children's playground for family fun
Motel
8.0
Great7171 reviews10
- Pet-friendly
- Hiking support
- Complimentary breakfast
From
US$ 182
/night
- Unique cottage-style architecture
- Special amenities for hikers
- Discounted tickets for local attractions
8.6
Great7373 reviews10
- Indoor Pool
- Fitness Centre
- Hot Tub
From
US$ 108
/night
- Close to Massachusetts Museum of Contemporary Art
- Indoor pool and hot tub available year-round
- On-site restaurant with local cuisine options
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