Find LGBTQ welcoming hotels in Chestertown, NY

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Top Chestertown LGBT Welcoming Hotels

Pine Tree Motel & Cabins
2 out of 5
5537 State Route 8, Chestertown, NY
The price is AU$296 per night from 3 Aug to 4 Aug
AU$296
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (130 reviews)
"Beautiful property Owners are so nice Can't wait to come back and stay"

Reviewed on 20 Jul. 2025

Pine Tree Motel & Cabins
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.

Enjoy gay-friendly hotels in Chestertown


What kinds of gay-friendly hotels are there in Chestertown?


When you're looking for gay-friendly hotels in Chestertown, you'll find a wide variety of options to choose from. These welcoming hotels come in all shapes and sizes and offer a diverse array of amenities and special features you can enjoy. Whether you're looking for something romantic, like hotels with spa facilities, or are more interested in rooms better fit for a solo traveller or a group of friends, you'll find it here. What these hotels all have in common, though, is strict anti-discrimination policies and insight into some of the most popular LGBTQ-friendly activities available in town.


What are the best gay-friendly hotels in Chestertown like?


The best gay-friendly hotel in Chestertown depends on what you're looking for in accommodation. Fortunately, you can easily find what you need, thanks to the multitude of available search filters. You can filter based on amenities you may be interested in, like hot tubs or pet-friendly policies, or you can sort by star rating. You can even filter by guest reviews to show only hotels that have received predominantly high marks from previous guests. Don't forget to mark the filter for LGBTQ-friendly hotels to only show anti-discriminatory hotels in your results.


How can I find deals on Chestertown gay-friendly hotels?


You'll find plenty of deals on gay-friendly hotels in Chestertown. If you want to increase your chances of finding a deal, try booking your stay in the off-season when prices are usually cheaper. Additionally, think about what amenities you may be willing to go without to drive the price down even further. Of course, booking a short distance away from prominent attractions can be an easy way to save while still being close to public transport routes that can get you to the action easily. Just keep in mind that these are general trends rather than solid rules, as prices fluctuate all the time and can be difficult to predict.


Why should I book a gay-friendly hotel in Chestertown with Expedia?


Booking with Expedia makes your holiday planning easier than ever before. Not only will you be able to enjoy a massive selection of gay-friendly hotels in Chestertown, but you can also book a flight as well. In fact, booking both through Expedia may even unlock some additional savings. Plus, you can take advantage of the Expedia Rewards program. Joining is completely free, and every booking earns you points that you can redeem later for additional discounts. Plus, you'll enjoy deep discounts on certain hotels simply by being a member.


Are gay-friendly hotels in Chestertown fully refundable?


A fully refundable cancelation is a handy feature to have, and numerous gay-friendly hotels in Chestertown offer it. Expedia is proud to host a wide variety of hotels that offer full refund – there's even a search-filter option for it. You'll be able to see all qualifying hotels clearly marked on your search results page without even having to click the hotels individually.