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Hotel vacation rentals in Berkshire County

Find and book unique hotel rentals on Airbnb

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Top-rated hotel rentals in Berkshire County

Guests agree: these hotel rentals are highly rated for location, cleanliness, and more.

Guest favorite
Nature lodge in Sheffield
Sheffield Lodge - Ramblewood Master
The Sheffield Lodge is a warm and inviting rustic Bed and Breakfast secluded from city life nestled in a pine forest. Enjoy your home-away-from-home where there is always friendly service, delicious breakfasts, afternoon treats. The lodge features an inviting fireplace, large screen TV, game table for board games or cards and a quiet reading/living room, and ample parking. Outdoor recreation is within minutes in every direction. There are museums, shops and many great restaurants nearby.
$160 per night
Superhost
Hotel room in Lee
Great place|2 BD|Kitchen| Pool 
After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge .
$162 per night
Superhost
Hotel room in Lee
Great place for family |2 BD|Kitchen| Pool
After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 
$161 per night

Popular amenities for Berkshire County hotel rentals

Family-friendly hotel rentals

Boutique hotel in Lee
The Chambery Inn: La Savoie - Deluxe Jacuzzi Suite
$313 per night
Resort in Lee
Villa in Beautiful Berkshires Resort, Lee MA
$370 per night
Boutique hotel in Williamstown
Brookside Traditional Doubles
$162 per night
Hotel room in Hancock
Wyndham Bentley Brook * Studio
$164 per night
Boutique hotel in Lee
The Chambery Inn: School House Suite
$274 per night
Hotel in Williamstown
Barnside Turn of the Century Luxury Suite 202
$312 per night
Hotel in Williamstown
Barnside Victorian Luxury Suite 204
$271 per night
Boutique hotel in Lee
Chambery Inn: L'Atelier - Economy Queen Room
$239 per night
Boutique hotel in Lee
Chambery Inn: La Chambrette - Economy King Room
$238 per night
Hotel in Williamstown
Brookside Country King
$169 per night
Hotel in Williamstown
Barnside Empire Luxury Suite 206
$271 per night
Hotel in Williamstown
Barnside Early American Luxury Suite 201
$242 per night

Hotel rentals with a pool

Superhost
Resort in Hancock
Country Inn Suite at Jiminy Peak - No fees added
$389 per night
Superhost
Hotel in Hancock
Bentley Brook- 1 bedroom
$78 per night
Guest favorite
Hotel in Lenox
Cecile's and Apple Tree Inn w/ Queen Bed
$139 per night
Guest favorite
Boutique hotel in Lenox
★ Romantic King Room w/ Double Jacuzzi & Fireplace
$999 per night
Resort in Hancock
Club Wyndham Bentley Brook - Two Bedroom Suite
$173 per night
Boutique hotel in Lenox
Room 10: Alice's Room - Apple Tree Inn
$999 per night
Hotel in Lee
Oak N' Spruce Resort
$131 per night
Boutique hotel in Williamstown
3 Bed | 2 Bath - 5 minutes to Jimminy Peak
$263 per night
Resort in Pittsfield
Berkshire Mass. Resort, 1bdrm 8/27-9/03 $1050
$150 per night
Superhost
Hotel room in Lee
Great Place |2 BD|Kitchen| Pool 
$162 per night
Superhost
Hotel room in Lee
Great Place|2 BD|Kitchen| Pool 
$162 per night
Superhost
Hotel room in Lee
Great place|2 BD|Kitchen| Pool 
$161 per night

Hotel rentals with a patio

Superhost
Hotel in Lee
Villa in the Berkshires
$400 per night
Resort in Hancock
Large 1 Bedroom- Vacation Village in Berkshires
$132 per night
Aparthotel in Spencertown
Spencertown Inn Suite 3
$239 per night
Superhost
Hotel room in Lee
Great place|2 BD|Kitchen| Pool 
$161 per night
Superhost
Hotel room in Lee
Great place|2 BD|Kitchen| Pool
$162 per night
Superhost
Hotel room in Lee
Great Place|2 BD|Kitchen| Pool 
$162 per night
Superhost
Hotel room in Lee
Beautiful place|2 BD|Kitchen| Pool
$162 per night
Superhost
Hotel room in Lee
Great for family|2 BD|Kitchen| Pool
$162 per night
Superhost
Hotel room in Lee
Great place|2 BD|Kitchen| Pool
$162 per night
Superhost
Hotel room in Lee
Great place|2 BD|Kitchen| Pool 
$161 per night
Hotel room in Hancock
Wyndham Bentley Brook * 1 Bedroom
$234 per night
Resort in Pittsfield
Charming 1 Bedroom - 4 Star Resort w/ pool
$138 per night

Destinations to explore