Hotel vacation rentals in Berkshire County

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Top-rated hotel rentals in Berkshire County

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Resort in Hancock

4.54 out of 5 average rating, 72 reviews

Club Wyndham Bentley Brook - Two Bedroom Suite

Club Wyndham Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this resort an exceptional choice for mountainside play. Ski or snowboard down the well-groomed trails of Jiminy Peak, enjoy hiking, tennis and mountain biking, or swimming at the on-site pools. This suite offers a king bed in the master bedroom, two full beds in the guest bedroom and a sleeper sofa in the living room. Additional amenities include a kitchen and dining area, washer/dryer and a balcony.

Oct 5 – 12

ﺩ.ﺇ460 per night

Guest favorite

Nature lodge in Sheffield

4.98 out of 5 average rating, 43 reviews

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.

Sep 16 – 23

ﺩ.ﺇ576 per night

Boutique hotel in Lenox

5.0 out of 5 average rating, 3 reviews

★ Beautiful Room with Fireplace & Jacuzzi Tub

Known as the Sunol Room, this beautiful second-floor room features a Queen bed, corner gas fireplace and private bath with a Jacuzzi tub. Located in the Carriage House of our historic property, this room offers luxurious amenities, privacy and is a short walk to downtown Lenox. Professionally managed by Hampton Terrace Inn, you can be assured of quality and cleanliness. Please note: Breakfast & housekeeping services are not included with our discounted off-season rates from November - April.

Apr 1 – 8

ﺩ.ﺇ4,187 per night

Hotel in Lenox

5.0 out of 5 average rating, 4 reviews

Shadowbrook and Apple Tree Inn w/ Mountain View

Apple Tree Inn sits on 22 acres in the beautiful Berkshires. It has a seasonal outdoor swimming pool, free WiFi, a bar w/ live music, a restaurant, and complimentary European-style breakfast. No televisions available to encourage guests to enjoy the scenery. Tanglewood is a 10-minute walk. Please note that this room is above the bar. Guests staying here from Wednesday to Saturday may hear music until 11:00 p.m. Earplugs can be provided. Daily housekeeping can be accommodated for a fee.

Jan 30 – Feb 6

Hotel vacation rentals in Berkshire County

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