Top Resorts in The Berkshires
Find the Top Resorts in The Berkshires – 80+ Quality Options from Leading Providers
21-40 out of 87 resorts
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8.4
Great5353 reviews10
From
US$ 131
/night
- On-site Pan-Asian restaurant Jae's
- Inviting patio with gas fireplace
- Accessibility features for special needs
Bed & Breakfast
8.4
Great8282 reviews10
From
US$ 129
/night
- Gourmet breakfast with specialty coffees
- Designer rooms with private balconies
- Private deck next to koi pond
Hotel
8.0
Great2727 reviews10
- On-site Spa
- Event Barn
- Artisan Kitchen
From
US$ 249
/night
- Renowned for unique weddings and events
- Locally sourced dining from artisanal kitchen
- Charming lodging in renovated dairy barn
8.6
Great167167 reviews10
- Indoor Pool
- Outdoor Pool
- Jacuzzi
From
US$ 139
/night
- Unique rooms with jacuzzis and fireplaces
- Indoor and outdoor pools for relaxation
- Complimentary breakfast with made-to-order omelets
Bed & Breakfast
8.0
Great3939 reviews10
- Private baths
- On-site dining
- Ski storage
From
US$ 171
/night
- Home-cooked breakfast served daily
- Historical bed and breakfast charm
- Wrap-around porches with great views
Hotel
8.2
Great2828 reviews10
- Restaurant
- Bar
- Private Parking
From
US$ 103
/night
- On-site restaurant and bar
- 24-hour reception service
- Air-conditioned rooms available
Bed & Breakfast
8.6
Great1919 reviews10
- Heated Pool
- Fitness Center
- Wine Lounge
From
US$ 354
/night
- Gourmet breakfast with unique daily offerings
- Three distinct pet-friendly lodging options
- Wine and cheese social hour
Bed & Breakfast
8.4
Great4949 reviews10
- Outdoor pool
- Wine bar
- Hiking trails
From
US$ 319
/night
- Unique elopement packages with planning assistance
- Gourmet farm-to-table breakfast served daily
- Scenic grounds for outdoor activities
8.2
Great5555 reviews10
- Indoor Pool
- Fitness Center
- Business Center
From
US$ 484
/night
- Indoor pool with hot tub access
- Complimentary hot breakfast served daily
- 24-hour fitness center for guests
Inn
8.4
Great5252 reviews10
- Lakefront Access
- Outdoor Firepit
- Gourmet Breakfast
From
US$ 513
/night
- Daily wine and cheese hour
- Gourmet breakfast featuring local ingredients
- Direct access to kayaking and paddleboarding
Bed & Breakfast
8.4
Great5656 reviews10
- Private Patios
- In-Room Breakfast
- Gas Fireplaces
From
US$ 358
/night
- In-room breakfast with homemade and fresh options
- Private entrances and outdoor patios for rooms
- Pet-friendly accommodations with thoughtful amenities
Hotel
- Private Parking
- Game Room
- Evening Entertainment
From
US$ 506
/night
- On-site restaurant with unique dining options
- 24-hour reception in English and Spanish
- Air-conditioned rooms with iPad amenities
Inn
8.2
Great2222 reviews10
- Gourmet Breakfast
- Artful Design
- Dog-Friendly Rooms
From
US$ 614
/night
- Handmade Hästens mattresses for luxury comfort
- Exquisite breakfast with homemade variety
- Personalized service for special occasions
8.6
Great6363 reviews10
- Private Dining
- Heated Floors
- Craft Cocktails
From
US$ 47
/night
- Gourmet breakfast made to order
- Breathtaking views of the Berkshires
- Live piano music in the lounge
Motel
8.4
Great101101 reviews10
- Heated Pool
- Garden Seating
- Pet Amenities
From
US$ 89
/night
- Heated outdoor pool with mountain views
- Charming garden areas for relaxation
- Pet-friendly amenities for travelers
Hotel
9.0
Perfect1010 reviews10
- Dining Tavern
- Sauna
- Swimming Pool
- Scenic hiking to a waterfall
- Prepared-to-order breakfast
- Relaxation areas with hammocks
Motel
8.2
Great8989 reviews10
- Ski storage
- Playground
- On-site dining
From
US$ 148
/night
- On-site restaurant serving American cuisine
- Ski storage and waxing area available
- Children's playground for family fun
Hotel
9.2
Perfect6666 reviews10
- Outdoor Pool
- On-site Spa
- Tennis Court
From
US$ 395
/night
- Seasonal outdoor swimming pool
- On-site spa and wellness centre
- Restaurant serving American cuisine
Hotel
9.4
Perfect3131 reviews10
- On-site spa
- Swimming pool
- Picnic area
From
US$ 515
/night
- Extensive property restoration planned by 2026
- Inviting on-site spa and wellness facilities
- Outdoor swimming pool for guest relaxation
8.6
Great7373 reviews10
- Indoor pool
- Fitness center
- Hot tub
From
US$ 108
/night
- Close to Massachusetts Museum of Contemporary Art
- Indoor pool and hot tub for relaxation
- On-site restaurant with local dishes
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