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Gay Accommodations & Gay Bnbs in Westchester
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Hosted by Tavares
Entire place • Westchester
Stunning 2Bdrm Westchester Home!
2 Bedrooms • 2 Beds • 2 Bathrooms
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Keep searching in the city: Trusted gay-friendly stays
Gay travel is a niche market, which is why our inventory here is sometimes limited. By booking one of these LGBTQ+ friendly stays, you directly help misterb&b fund its mission: recruiting new gay hosts and covering the complex legal and regulatory costs we face. Give your stay meaning - book your favorite below!
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Instant bookingHotel *** • Westchester
4.44 (1)
Four Points by Sheraton Chicago Westchester/Oak Brook
Parking • Gym • Restaurant
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Entire place • Westchester
Westchester Retreat King bed
3 Bedrooms • 3 Beds • 2 Bathrooms
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Entire place • Westchester
Near Brookfield Zoo - King Bed - Sleeps 7
1 Bedroom • 2 Beds • 1 Bathroom
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Entire place • Westchester
Beautiful Bright 2 bed - Near downtown Chicago
1 Bedroom • 3 Beds • 1 Bathroom
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Entire place • Westchester
Cozy Westchester Retreat Near Chicago & Parks
4 Bedrooms • 4 Beds • 2 Bathrooms
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Entire place • Westchester
Near Chicago - Sleeps 10 - Westchester
2 Bedrooms • 0 Beds • 1 Bathroom
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Stays near Westchester
These stays match your search but are located outside Westchester.
Hosted by Mike
Instant booking
Entire place • 13.5 miles from Westchester
4.65 (1)
The Huron Loft | Near Magnificent Mile
9 min · Frenchy’s (Gay Saunas & Cruising)1 Bedroom • 1 Bed • 1 Bathroom
Hosted by Mike
Instant booking
Entire place • 7.5 miles from Westchester
Booked 3 times
5 (1)
Modern Elegance: 4BR Duplex w/ Free Garage Parking
4 Bedrooms • 5 Beds • 2 Bathrooms
Jarred·5·Jul. 2026· "My friends and I had a great time here! The home was clean, with every room accurately reflecting what we saw in pictures. We received communications prior to our stay about check-in procedures. The home is about 30-40 minutes from the gay district, Northalsted. Front gate remains locked, so entrance can only be from the back of the house through the garage. Amenities worked great! Washer/dryer was simple to use, AC worked great, however the dishwasher's top rack was missing support, but did not interfere with completing a cycle."
Hosted by Mike
Instant booking
Entire place • 3.7 miles from Westchester
4.8 (1)
Whispering Oaks Retreat!
5 Bedrooms • 5 Beds • 2 Bathrooms
Hosted by Mike
Instant booking
Entire place • 4.1 miles from Westchester
4.58 (1)
Pearly Gates w/ 2-Car Garage
3 Bedrooms • 3 Beds • 1 Bathroom
Hosted by Billy
Instant booking
Entire place • 10.5 miles from Westchester
4.7 (1)
2-Bed 2-Bath Apt | close to UC w/ Free Parking
2 Bedrooms • 2 Beds • 2 Bathrooms