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Find Gay friendly Hotels in Cheshire, MA

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Check availability on Cheshire Gay friendly Hotels

Tonight
Jul 30 - Jul 31
Tomorrow
Jul 31 - Aug 1
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top Cheshire Gay friendly Hotels

Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"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$7,760
NT$8,202 total
includes taxes & fees
Aug 12 - Aug 13
Harbour House Inn
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"Clean,friendly staff and great location."
The price is NT$5,032
NT$5,621 total
includes taxes & fees
Aug 7 - Aug 8
Hotel Downstreet, Ascend Hotel Collection
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (395)
"No frills but it was a great stay!"
The price is NT$3,267
NT$3,649 total
includes taxes & fees
Aug 18 - Aug 19
Sunset Inn
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, (682)
"Had a great time"
The price is NT$3,794
NT$4,653 total
includes taxes & fees
Aug 6 - Aug 7
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is NT$6,113
NT$6,829 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Lenox Pittsfield
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Good lodgings in a great area to visit."
The price is NT$5,032
NT$5,620 total
includes taxes & fees
Aug 25 - Aug 26
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, (838)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is NT$3,831
NT$4,279 total
includes taxes & fees
Aug 17 - Aug 18
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is NT$6,005
NT$6,708 total
includes taxes & fees
Aug 17 - Aug 18
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, (1000)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is NT$3,958
NT$5,582 total
includes taxes & fees
Aug 27 - Aug 28
The Cornell Inn, Lenox & The Berkshires
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (477)
"All was just as advertised and the family/staff was friendly and helpful. "
The price is NT$5,148
NT$5,750 total
includes taxes & fees
Aug 3 - Aug 4
Whistler's Inn Bed & Breakfast
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.

Top Cheshire Hotel Reviews

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 and St Mary's of the Assumption Church.
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.