Visit Tillson: 2026 Travel Guide for Tillson, New York

Beekman Arms and Delamater Inn

6387 MILL ST Rhinebeck NY

$152 nightly

$172 total

Sep 9 - Sep 10

Total with taxes and fees

Book a stay at this business-friendly inn in Rhinebeck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

8.4/10 Very Good! (1,008 reviews)

"Had a really lovely stay at the beautiful and historical Beekman. For being americas oldest inn our room felt very clean spacious and well maintained. We had our pup with us and he loved it too. The building is very special obviously. Can’t beat the location as well!"

Reviewed on Sep 7, 2026

Holiday Inn Express Poughkeepsie by IHG

2750 South Road Poughkeepsie NY

$82 nightly

$96 total

Sep 13 - Sep 14

Total with taxes and fees

Stay at this hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...

Hyatt Place Poughkeepsie / Hudson Valley

2165 South Road Poughkeepsie NY

$101 nightly

$117 total

Sep 20 - Sep 21

Total with taxes and fees

Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

9/10 Wonderful! (1,064 reviews)

"The property itself was well maintained, our room was very clean but the beds were HORRIBLE. We did not sleep well at all during our stay, the mattresses both had a dent in the middle like a bowl, poor quality for the prize that is charged per night I definitely would expect a mattress like this ..."

Reviewed on Sep 7, 2026

See all 1,400 properties in Tillson

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.

The Chicken Coop

Staatsburg NY

Stay at this vacation home in Staatsburg. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Margaret Lewis Norrie State Park and Ogden Mills ...

9.8/10 Exceptional! (31 reviews)

"The Chicken Coop is somewhat rustic, but we enjoyed it very much. The fresh eggs and honey samples were a real treat. We would happily stay there again. The host was a great communicator."

Reviewed on Sep 6, 2026

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Saugerties NY

Stay at this cabin in Saugerties. Enjoy laundry facilities, patios, and in-room fireplaces. Popular attractions Vinnie's Farm Market and Saugerties Town Hall ...

8/10 Very Good! (51 reviews)

"This listing is a rustic cabin with a small loft for sleeping. There is no bathroom, no electricity, no running water and no refridgeration. Too darned rustic for a couple in their 70's with 2 dogs.The owner, Andrew, was kind, and helpful with location questions and responses. He did offer to refund ..."

Reviewed on Aug 17, 2026

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY

Stay at this cottage in Woodstock. Enjoy free WiFi, a garden, and patios. Our guests praise the property condition in our reviews. Popular attractions Woodstock ...

10/10 Exceptional! (297 reviews)

"Great location that feels secluded but is within walking distance to town. Nice to fall asleep with the windows open to the sounds of the stream."

Reviewed on Sep 6, 2026

See all properties in Tillson

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.

Frequently asked questions

When is the best time to visit Tillson?

The best time to visit Tillson is from May through September, when the weather is generally warm and pleasant for exploring. For travelers seeking fewer crowds and better value, the quieter winter months of December through March are a good option, offering a different, cooler experience.

Can I book a refundable hotel in Tillson?

Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Tillson by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.

Why book a trip to Tillson with Expedia?

Expedia makes it easier to plan your Tillson trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.

Should I stay in a hotel or vacation rental in Tillson?

The best choice depends on your travel style. Hotels in Tillson can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.

How can I manage my Tillson trip on Expedia?

Once you've booked your Tillson trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.

What if I need help during my Tillson trip?

Expedia offers customer support before, during, and after your Tillson trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.

How can Expedia help me plan my first trip to Tillson?

If it's your first trip to Tillson, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.

How can I save on my Tillson hotel booking with Expedia?

Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Tillson hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.