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Cheshire Hotel Guide - LGBT-Friendly Hotels in Cheshire, Massachusetts

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Check availability on Cheshire LGBT-Friendly Hotels

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

Our top choices for Cheshire LGBT-friendly hotels

Restaurant

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,003 reviews)
"Staff was fabulous and extremely helpful and friendly. Valey parking was terrific!!! and FREE Great to have since we had to park at the bank next to the hotel while there was construction in front of the building. Rooms were tidy and very clean Breakfast was excellent with a large variety of offerings"
United States
Margaret
The price is €108
includes taxes & fees
5 Aug - 6 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

2. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is €234
includes taxes & fees
3 Aug - 4 Aug
Harbour House Inn
Front of property

3. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,002 reviews)
"Quick check in and comfortable bed in a pretty New England town."
United States
William
The price is €167
includes taxes & fees
16 Aug - 17 Aug
Hotel Downstreet, an Ascend Collection Hotel
Property grounds

4. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (628 reviews)
"I was very satisfied with the stay. The room was extremely clean and comfortable. The outdoor space was very pleasant and peaceful; a beautiful setting. The staff was courteous and helpful."
United States
james
The price is €126
includes taxes & fees
9 Aug - 10 Aug
Maple Terrace Motel
Free daily buffet breakfast

5. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great comfortable beds Good breakfast"
United States
Nancy
The price is €159
includes taxes & fees
23 Aug - 24 Aug
Hampton Inn & Suites Berkshires-Lenox
Miscellaneous

6. 1896 House Country Inn & Motels

1896 House Country Inn & Motels
2.5 star property
Williamstown
6.6 out of 10, (453 reviews)
"Older strip type motel. That said room was clean and bed was comfortable. It was good for a couple of days that I stayed. No breakfast available at motel though they did give me a discount coupon to bar/resturant next door. "
United States
William
The price is €103
includes taxes & fees
4 Aug - 5 Aug
1896 House Country Inn & Motels
Breakfast, lunch and dinner served

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (698 reviews)
"Five Star stay!"
United States
Adeline
The price is €187
includes taxes & fees
23 Aug - 24 Aug
Hilton Garden Inn Lenox Pittsfield
Property amenity

8. Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
3.0 star property
Williamstown
8.8 out of 10, Excellent, (421 reviews)
"clean room and fast response to request"
United States
hui
The price is €222
includes taxes & fees
12 Aug - 13 Aug
Fairfield Inn & Suites by Marriott Williamstown
Seasonal outdoor pool

9. Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (428 reviews)
"It was a great stay, close to many amenities. The room was clean, with a comfortable bed."
Canada
Kevin
The price is €95
includes taxes & fees
17 Aug - 18 Aug
Sunset Inn
Property amenity

10. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (643 reviews)
"I usually stay here when I'm going to a concert at Tanglewood, it's comfortable, quiet, and convenient. The staff are really friendly. There's a Tesla EV charging station directly across Route 20 from the hotel."
United States
Michael
The price is €206
includes taxes & fees
19 Aug - 20 Aug
Courtyard by Marriott Lenox Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cheshire Hotel Reviews

Frequently asked questions

Looking for an LGBTQ-friendly hotel in Cheshire?
If you're interested in booking a place where you'll feel at ease in Cheshire, our website has the gay-friendly hotel you're looking for. Discover the people, places and traditions found only in Cheshire.
What is the favourite LGBTQ-friendly place to stay in Cheshire?
Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi.
What should I see while I'm in Cheshire?
During your trip, get out and enjoy everything Cheshire has to offer. You and your travelling companions may want to visit Mount Greylock State Reservation and Cheshire Reservoir.
What is a gay-friendly hotel in Cheshire?
LGBTQ-friendly hotels, also known as gay-friendly hotels, welcome all travellers who identify as LGBTQIA+. You'll find a selection of LGBTQ-friendly accommodation options on our site. In Cheshire, these hotels will provide lesbian, gay, bisexual and transgender adventurers with the information needed to design the trip of a lifetime.
What can I expect from a gay-friendly hotel in Cheshire?
Take a holiday from the ordinary; stay at a gay-friendly hotel in Cheshire, and you'll be around like-minded people, so you can relax and enjoy your trip. Some of Expedia's LGBTQ-friendly hotels go the extra mile and offer wedding ceremonies and honeymoon packages for same-sex couples.

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