Title: Book the Best Pittsfield GAY-FRIENDLY Hotels in 2025 | Expedia.ca [Pittsfield Travel Guide](https://expedia.ca/Pittsfield.dx146411)[Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d146411.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d146411.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d146411.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d146411.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d146411.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/20ffc1c1fd9890df2c042f65a516b89f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Find LGBTQ welcoming hotels in Pittsfield, IL ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Top Pittsfield LGBT Friendly Hotels ![William Watson Hotel](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1_y.jpg?impolicy=resizecrop&rw=340&ch=150) [William Watson Hotel](https://expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) 105 East Washington Street, Pittsfield, IL CA $123 CA $136 total Oct 16 - Oct 17 includes taxes & fees 9.2/10 Wonderful! (244 reviews) "The room was clean. All the outlets worked and the shower is nice. There are several nice restaurants in a walkable distance. I'd suggest letting the staff know if you will be arriving past 5pm. Check in and check out was very simple. I did not get to sample the breakfast as I was out before it even ..." Reviewed on Oct 5, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F10%2F2025&endDate=17%2F10%2F2025&selected=6659525&PinnedHotelID=6659525&HadPinnedHotel=true®ionId=146411&travelerType=LGBT) 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. [See all LGBTQ welcoming stays in Pittsfield](https://expedia.ca/Hotel-Search?regionId=146411&propertyStyle=LGBT&travelerType=LGBT) ## Find the top gay-friendly hotels in Pittsfield #### Are gay-friendly hotels in Pittsfield available? Yes, Pittsfield gay-friendly hotels are available in abundance throughout the area. These hotels come in a wide variety of configurations as well, allowing you to customize your vacation whether you're looking for something budget-friendly or something more luxurious. Room configurations, amenities, styles and more can all be customized as you see fit based on the kind of vacation experience you're looking for. Plus, these hotels have strict policies against discrimination and typically are in the know regarding the best LGBTQ-friendly activities in town. #### How can I find the best gay-friendly hotels in Pittsfield? Finding Pittsfield gay-friendly hotels is easy, thanks to our search filters. You'll find a massive array of filters, so you can sort your results to only show hotels that cater specifically to your desired vacation experience. You can implement filters for amenities in your hotel as well as for star ratings and guest reviews. You'll even find filters for price, so you can limit your results to only show hotels that are within your established budget. Additionally, you'll find a filter for LGBTQ-friendly hotels, so be sure to activate that one to sort all the non-accommodating hotels out of your search results. #### How can I find top deals on gay-friendly hotels in Pittsfield? To find deals, you'll want to take advantage of the various factors that affect hotel prices. These include the time of year, amenities, neighbourhood and more. Travelling during the off-season can net you lower prices, as can relinquishing amenities like spas and hot tubs. Additionally, booking outside of town can be cheaper than putting yourself right in the middle of the action. Don't forget to sort your search results by price as well to see the cheapest options for your hotel first. Gay-friendly hotels in Pittsfield have fluctuating prices, so it's important to remember that these are more general trends than rules set in stone. #### Why should I book Pittsfield gay-friendly hotels with Expedia? Booking with Expedia is among the easiest ways to ensure all your travel planning can be taken care of in a single, convenient place. Not only will you find an array of gay-friendly hotels in Pittsfield to choose from, but you'll find flights as well. The extensive search filters make finding the ultimate accommodation simple, as you can narrow down your search results to show only the hotels that fit your strict specifications. Plus, you can enjoy the Expedia Rewards program, which lets you earn points every time you book. Those points can be redeemed for discounts on future bookings, but that's just the beginning. Some accommodation options have special discounts only available to members. Becoming a member is free, so don't hesitate to take advantage. ## LGBTQ-welcoming hotels in top travel spots ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_Montreal_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Montreal [](https://expedia.ca/Hotel-Search?regionId=178288&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_Palm_Springs_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Palm Springs [](https://expedia.ca/Hotel-Search?regionId=180676&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_Puerto_Vallerta_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Puerto Vallarta [](https://expedia.ca/Hotel-Search?regionId=180016&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_Key_West_Florida_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Key West [](https://expedia.ca/Hotel-Search?regionId=1187&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_Miami_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Miami [](https://expedia.ca/Hotel-Search?regionId=8833&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_Cancun_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Cancun [](https://expedia.ca/Hotel-Search?regionId=179995&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_Paris_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Paris [](https://expedia.ca/Hotel-Search?regionId=179898&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_Amsterdam_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Amsterdam [](https://expedia.ca/Hotel-Search?regionId=178229&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_Barcelona_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Barcelona [](https://expedia.ca/Hotel-Search?regionId=179992&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_London_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### London [](https://expedia.ca/Hotel-Search?regionId=178279&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_NYC_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### New York [](https://expedia.ca/Hotel-Search?regionId=178293&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_San_Francisco_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### San Francisco [](https://expedia.ca/Hotel-Search?regionId=178305&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_Chicago_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Chicago [](https://expedia.ca/Hotel-Search?regionId=178248&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ![](https://forever.travel-assets.com/flex/flexmanager/images/2021/02/17/ORB_LA_c.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) ### Los Angeles [](https://expedia.ca/Hotel-Search?regionId=178280&rfrr=HTG.LGBTQ.Tile&travelerType=LGBT) ## Explore a world of travel with Expedia - 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