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Hotel vacation rentals in Berkshire County

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Top-rated hotels in Berkshire County

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

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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.

Sep. 20 – 27

$195 CAD per night

Guest favourite

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.

Dec. 31 – Jan. 7

$242 CAD 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.

Mar. 14 – 21

$1,765 CAD per night

Hotel room in Lee

5.0 out of 5 average rating, 3 reviews

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 

Oct. 26 – Nov. 2

$290 CAD per night

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 .

Jan. 28 – Feb. 4

$275 CAD per night

Hotel room in Lee

4.75 out of 5 average rating, 8 reviews

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 

Dec. 26 – Jan. 2

$459 CAD per night

Hotel room in Lee

New place to stay

Good Place 2BD/2BA +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 

Nov. 16 – 23

$275 CAD per night

Boutique hotel in Cummington

4.81 out of 5 average rating, 80 reviews

Singing Bridge Harmony Room

Great views of the Berkshire hilly forests, and hiking trails along a scenic river. Couples, families, and pets feel right at home in our recently renovated kitchen and warm, and friendly lodge with four bedrooms, electric baseboard heat and queen-sized beds. The sunny loft has a comfy queen. Gas heat. Call an hour before arrival if you don't have AT&T or Verizon cell service- other carriers may be inconsistent in the area. Wifi enabled. Pets are welcome for a $25 fee.

Mar. 17 – 24

$132 CAD per night

Hotel in Adams

5.0 out of 5 average rating, 3 reviews

The Trail in Adams - Deluxe Room

Welcome to "The Trail in Adams" - Berkshires’ Art Hotel on the Ashuwillticook Rail Trail in Adams. Jon is a 288 square feet deluxe room on the second floor with a king-size bed, a 13.5-foot ceiling, a walk-in closet, an ensuite bathroom with spa tub (indoor), south and east-facing windows, and a view of Pleasant St.

May 6 – 13

$225 CAD per night

Hotel in Lee

Villa in the Berkshires Presidential Suite

2 bedroom- 2 bathroom Presidential Villa suite located in the Berkshires Massachusetts. The location is situated and close to many area attractions. There are plenty of fun things for the kids, including an indoor pool and game room. Perfect for families who want to explore nature, museums, and local culture.

Mar. 24 – 31

$726 CAD per night

Boutique hotel in Lee

5.0 out of 5 average rating, 5 reviews

The Chambery Inn: La Savoie - Deluxe Jacuzzi Suite

This listing is for our Firespa suite on lower level. With King bed, Fireplace, and Large 2 person jacuzzi this room is typically reserved for in room couples massages and romantic getaways. Central to all Berkshire activities and the only hotel on main street, walk to the areas best dining and shopping!

Jan. 5 – 12

$515 CAD per night

Boutique hotel in Lenox

4.63 out of 5 average rating, 267 reviews

Standard King in Boutique Lenox Hotel

Designed to relax and inspire, our Standard King guest room is furnished with a writer's desk and harmonious color tones drawn from the seasonal hues of the Berkshires. As always, stocked with luxe touches such as plush linens and terry robes from Revival New York and Le Labo shower amenities.

Feb. 3 – 10

$166 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Berkshire County hotels

Free parking on premises

Air conditioning

Family-friendly hotels

Hotel room in Hancock

5.0 out of 5 average rating, 4 reviews

Wyndham Bentley Brook * Studio

Mar. 17 – 24

$409 CAD per night

Boutique hotel in Lee

4.5 out of 5 average rating, 4 reviews

The Chambery Inn: School House Suite

Mar. 4 – 11

$515 CAD per night

Boutique hotel in Lee

Chambery Inn: La Chambrette - Economy King Room

Dec. 15 – 22

$440 CAD per night

Boutique hotel in Lee

Chambery Inn: L'Atelier - Economy Queen Room

Oct. 1 – 8

$493 CAD per night

Hotels with a pool

Resort in Pittsfield

Berkshire Mass. Resort, 1bdrm 8/27-9/03 $1050

May 28 – Jun. 4

$265 CAD per night

Hotel room in Lee

New place to stay

Good Place 2BD/2BA

Mar. 12 – 19

$335 CAD per night

Hotel room in Lee

New place to stay

Great place|2 BD|Kitchen| Pool 

Apr. 25 – May 2

$335 CAD per night

Hotel room in Lee

New place to stay

Good Place with Kitchen+Pool

Feb. 11 – 18

$290 CAD per night

Hotel room in Lee

Great Place|2 BD|Kitchen| Pool 

Sep. 19 – 26

$324 CAD per night

Hotel room in Lee

Great place|2 BD|Kitchen| Pool 

Nov. 30 – Dec. 7

$275 CAD per night

Hotel room in Lee

New place to stay

Great Place - Kitchen+Pool - 2BD

Oct. 16 – 23

$324 CAD per night

Hotel room in Lee

Great Place |2 BD|Kitchen| Pool 

Apr. 27 – May 4

$335 CAD per night

Hotels with a patio

Resort in Pittsfield

Charming 1 Bedroom - 4 Star Resort w/ pool

Sep. 20 – 27

$243 CAD per night

Aparthotel in Spencertown

Spencertown Inn Suite 3

Oct. 18 – 25

$357 CAD per night

Hotel room in Lee

Great place|2 BD|Kitchen| Pool 

Feb. 2 – 9

$275 CAD per night

Hotel room in Lee

Great Place|2 BD|Kitchen| Pool 

Mar. 24 – 31

$335 CAD per night

Hotel room in Lee

Great place|2 BD|Kitchen| Pool 

Apr. 2 – 9

$335 CAD per night

Hotel room in Lee

Great place|2 BD|Kitchen| Pool 

Feb. 8 – 15

$279 CAD per night

Hotel room in Lee

Great place|2 BD|Kitchen| Pool

Jun. 8 – 15

$402 CAD per night

Hotel room in Lee

Great for family|2 BD|Kitchen| Pool

May 23 – 30

$391 CAD per night

Destinations to explore