Find Gay friendly Hotels in Winchester, MA

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Check availability on Winchester Gay friendly Hotels

Our top choices for Winchester LGBT-friendly hotels

International cuisine
citizenM Boston Back Bay

citizenM Boston Back Bay

citizenM Boston Back Bay
4.0 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (2119)
"Always enjoy staying there"
United States
Justin
The price is ₩158,115
₩184,125 total
includes taxes & fees
Dec 21 - Dec 22
citizenM Boston Back Bay
Standard Room, 1 Queen Bed | Premium bedding, in-room safe, iron/ironing board, free WiFi
Found Hotel Boston Common

Found Hotel Boston Common

Found Hotel Boston Common
2.5 star property
Bay Village
8.2 out of 10, Very Good, (1264)
"I always like staying here "
United States
Sonia
The price is ₩138,979
₩161,841 total
includes taxes & fees
Dec 21 - Dec 22
Found Hotel Boston Common
In-room safe, blackout drapes, iron/ironing board, free WiFi
Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel
4.0 star property
Back Bay
8.6 out of 10, Excellent, (3910)
"Great for a short stay option. We stayed 2 days and it was perfect for our needs. "
United States
Rocco
The price is ₩117,921
₩137,319 total
includes taxes & fees
Dec 25 - Dec 26
Copley Square Hotel, a FOUND Hotel
Lobby
Hilton Boston Park Plaza

Hilton Boston Park Plaza

Hilton Boston Park Plaza
4.0 star property
Bay Village
8.4 out of 10, Very Good, (3110)
"Great stay! "
United States
Charles
The price is ₩165,134
₩252,516 total
includes taxes & fees
Dec 24 - Dec 25
Hilton Boston Park Plaza
Serves breakfast, lunch, and dinner
Moxy Boston Downtown

Moxy Boston Downtown

Moxy Boston Downtown
3.5 star property
Bay Village
8.8 out of 10, Excellent, (1006)
"Clean and the staff very nice "
United States
Juliana A
The price is ₩116,739
₩196,174 total
includes taxes & fees
Dec 22 - Dec 23
Moxy Boston Downtown
Interior
Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End
3.0 star property
South End
9.0 out of 10, Wonderful, (1001)
"Great stay"
United States
John
The price is ₩118,364
₩180,776 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Staypineapple, A Delightful Hotel, South End
Exterior
Hyatt Regency Boston

Hyatt Regency Boston

Hyatt Regency Boston
4.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (1711)
"Amazing room, friendly staff"
United States
Ryan
The price is ₩187,965
₩270,606 total
includes taxes & fees
Dec 28 - Dec 29
Hyatt Regency Boston
Courtyard
DoubleTree by Hilton Boston - Downtown

DoubleTree by Hilton Boston - Downtown

DoubleTree by Hilton Boston - Downtown
4.0 star property
Bay Village
8.8 out of 10, Excellent, (1006)
"Clean very nice room amd great staff"
United States
James
The price is ₩132,078
₩153,805 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Boston - Downtown
Bar (on property)
Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District
3.0 star property
Seaport District
9.4 out of 10, Exceptional, (2211)
"Very nice hotel and great location"
United States
Ann
The price is ₩206,879
₩240,910 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Hyatt Place Boston/Seaport District
Lobby
The Westin Boston Seaport District

The Westin Boston Seaport District

The Westin Boston Seaport District
4.0 star property
Seaport District
9.2 out of 10, Wonderful, (2324)
"Nice hotel and great location."
United States
James Earl
The price is ₩167,055
₩246,159 total
includes taxes & fees
Dec 22 - Dec 23
The Westin Boston Seaport District
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 Winchester Hotel Reviews

Hyatt Regency Boston

Hyatt Regency Boston

10/10 Excellent
"The staff was very friendly. Our room was very comfortable, and the dining was excellent."
Michelle 1-night trip
Posted 4 hours ago
Hyatt Regency Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

10/10 Excellent
"Yes the room was very clean and comfortable. "
Joanna 1-night trip
Posted 3 days ago
Hilton Boston Park Plaza

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Frequently asked questions

Looking for a gay-friendly hotel in Winchester?
Ready to leave ordinary life behind? If you want to book a place that will welcome you to Winchester, our website has the LGBTQ-friendly hotel you're looking for. Discover the people, places, and traditions found only in Winchester.
What is there to see in Winchester?
During your trip, get out and explore everything Winchester is known for. You and your traveling companions may want to visit Winter Pond and Middlesex Fells Reservation. While you're here, capture some great memories of your trip with stops at Fenway Park, Harvard Square, and TD Garden.
What is an LGBTQ-friendly hotel in Winchester?
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 Winchester, 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 Winchester?
Stay at an LGBTQ-friendly hotel in Winchester and you'll be around like-minded people, so you can relax and enjoy your trip. Many of our LGBTQ-friendly accommodations offer community-specific packages, exclusive tours, and opportunities for social interaction.