Photo by Ed Gaffny

Find Gay friendly Hotels in Cheshire, MA

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Cheshire Gay friendly Hotels

Tonight
Sep 27 - Sep 28
Tomorrow
Sep 28 - Sep 29
Next weekend
Oct 3 - Oct 5
In two weeks
Oct 10 - Oct 12

Top Cheshire Gay friendly Hotels

Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1008)
"Very clean, nice amenities , great location!!"
The price is NT$4,550
NT$5,082 total
includes taxes & fees
Sep 30 - Oct 1
Hampton Inn & Suites Berkshires-Lenox
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (882)
"Our stay was very pleasant "
The price is NT$3,318
NT$3,706 total
includes taxes & fees
Oct 5 - Oct 6
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (575)
"Excellent place. Bountiful view. "
The price is NT$4,231
NT$4,726 total
includes taxes & fees
Sep 28 - Sep 29
Maple Terrace Motel
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (52)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is NT$7,985
NT$8,440 total
includes taxes & fees
Sep 29 - Sep 30
Harbour House Inn
Hotel Downstreet, an Ascend Collection Hotel
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1011)
"Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool"
The price is NT$4,413
NT$4,930 total
includes taxes & fees
Oct 26 - Oct 27
Hotel Downstreet, an Ascend Collection Hotel
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (574)
"Fabulous place"
The price is NT$4,901
NT$5,475 total
includes taxes & fees
Sep 30 - Oct 1
Courtyard by Marriott Lenox Berkshires
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1005)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is NT$3,897
NT$5,546 total
includes taxes & fees
Oct 28 - Oct 29
The Cornell Inn, Lenox & The Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (738)
"The lodging was convenient to all the area attractions."
The price is NT$3,818
NT$4,691 total
includes taxes & fees
Sep 28 - Sep 29
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (405)
"The staff is a one man operation,Which he is a very nice man,does a good job keeping up with the cleaning.Location is great walking distance to the town and plenty of restaurants."
The price is NT$3,044
NT$3,400 total
includes taxes & fees
Oct 6 - Oct 7
Sunset Inn
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (646)
"We always stay at the Garden Inn when visiting the Berkshires."
The price is NT$4,963
NT$5,544 total
includes taxes & fees
Oct 1 - Oct 2
Hilton Garden Inn Lenox Pittsfield
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.
View all properties

Top Cheshire Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Looking for an LGBTQ-friendly hotel in Cheshire?
If you're searching for a place where you'll feel welcome in Cheshire, Expedia has all the gay-friendly hotels you'd wish for. Discover the people, places, and traditions found only in Cheshire.
What's the best LGBTQ-friendly accommodation in Cheshire?
Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi.
What are the top places to visit in Cheshire?
During your vacation, get out and discover all that Cheshire is known for. You and your traveling companions may want to visit Mount Greylock State Reservation.
What is a gay-friendly hotel in Cheshire?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual, and transgender travelers are proudly welcomed. We have worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of gay-friendly hotels worldwide. In Cheshire, hotels affiliated with IGLTA operate in a spirit of inclusiveness, prioritizing a diverse environment in which guests are welcomed, respected, and not obliged to declare or hide their sexual orientation.
What can I expect from a gay-friendly hotel in Cheshire?
Take a vacation from the ordinary; stay at a gay-friendly hotel in Cheshire, and the staff will help you explore the local gay scene and the LGBTQ+ culture. Some of Expedia's LGBTQ-friendly hotels go the extra mile and offer concierge services that provide information about nearby LGBTQ restaurants and local events.