Gay friendly Hotels in Cheshire, Massachusetts

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Our top choices for Cheshire LGBT-friendly hotels

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"Nice place for a weekend away."
United States
Gregory
The price is P12,730
P13,455 total
includes taxes & fees
Jan 19 - Jan 20
Harbour House Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (440)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is P6,470
P7,097 total
includes taxes & fees
Jan 13 - Jan 14
Shaker Mill Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1002)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is P5,565
P6,217 total
includes taxes & fees
Jan 10 - Jan 11
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (660)
" Nice staff - beautiful hotel!"
United States
MARY
The price is P7,571
P8,457 total
includes taxes & fees
Jan 23 - Jan 24
Hilton Garden Inn Lenox Pittsfield

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1001)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is P7,422
P8,290 total
includes taxes & fees
Feb 2 - Feb 3
Hotel Downstreet, an Ascend Collection Hotel

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Very comfortable beds! "
United States
Gerald
The price is P6,600
P7,373 total
includes taxes & fees
Jan 25 - Jan 26
Hampton Inn & Suites Berkshires-Lenox

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is P5,329
P5,952 total
includes taxes & fees
Jan 17 - Jan 18
Sunset Inn

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (595)
"Cute place"
United States
Lisa
The price is P5,861
P6,547 total
includes taxes & fees
Jan 11 - Jan 12
Maple Terrace Motel

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (818)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is P5,542
P7,348 total
includes taxes & fees
Jan 14 - Jan 15
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
Williamstown
8.8 out of 10, Excellent, (399)
"our stay was great."
United States
nathaniel
The price is P10,065
P11,243 total
includes taxes & fees
Jan 15 - Jan 16
Fairfield Inn & Suites by Marriott Williamstown
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.
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.

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