Search Gay-Friendly Hotels in Winchester

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

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, (2117)
"Always enjoy staying there"
United States
Justin
The price is ₹9,675
₹11,267 total
includes taxes & fees
21 Dec - 22 Dec
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 ₹8,504
₹9,903 total
includes taxes & fees
21 Dec - 22 Dec
Found Hotel Boston Common
In-room safe, blackout curtains, 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 ₹7,216
₹8,403 total
includes taxes & fees
25 Dec - 26 Dec
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 ₹10,105
₹15,451 total
includes taxes & fees
24 Dec - 25 Dec
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, (1004)
"Clean and the staff very nice "
United States
Juliana A
The price is ₹7,143
₹12,004 total
includes taxes & fees
22 Dec - 23 Dec
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 ₹7,243
₹11,062 total
includes taxes & fees
4 Jan - 5 Jan 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, (1709)
"Amazing room, friendly staff"
United States
Ryan
The price is ₹11,502
₹16,558 total
includes taxes & fees
28 Dec - 29 Dec
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 ₹8,082
₹9,411 total
includes taxes & fees
4 Jan - 5 Jan 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, (2209)
"Very nice hotel and great location"
United States
Ann
The price is ₹12,659
₹14,741 total
includes taxes & fees
13 Jan - 14 Jan 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 ₹10,222
₹15,063 total
includes taxes & fees
22 Dec - 23 Dec
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.
View all properties

Top Winchester Hotel Reviews

Hyatt Regency Boston

Hyatt Regency Boston

10/10 Excellent
"Great location, clean room, staff was accommodating, comfortable bar while waiting on family.. no complaints. Housekeeping did forget to leave fresh towels. This was easily resolved with a phone call & they arrived in a timely manner. "
Heather 3-night trip
Posted 4 days ago
Hyatt Regency Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

10/10 Excellent
"Personnel at front desk are extremely helpful and friendly."
Aileen 1-night trip
Posted 6 days ago
Hilton Boston Park Plaza

Explore a world of travel with Expedia

Frequently asked questions

How do I find a gay-friendly hotel in Winchester?
If you're searching for a place where you'll feel at ease in Winchester, our website has the LGBTQ-friendly hotel you're looking for. Discover the people, places and traditions found only in Winchester.
What should I see while I'm in Winchester?
During your trip, get out and enjoy everything Winchester has to offer. You and your travelling 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, also known as gay-friendly hotels, welcome all travellers who identify as LGBTQIA+. 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 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 Winchester?
Stay at a gay-friendly hotel in Winchester and you won't have to hide or your sexuality or your gender identity when you check in. Many of our LGBTQ-friendly accommodation options offer concierge services that provide information about nearby LGBTQ restaurants and local events.