Pawling, NY

Travel Guide

A wooden boardwalk with a wooden chair and a sign reading "Swamp River Boardwalk."
A wooden boardwalk through a lush, green landscape with trees and wildflowers.
A wooden boardwalk curving through a field of purple flowers under a clear sky.
A wooden boardwalk through a field of tall grasses with a bench on the side.
A wooden boardwalk through a field of tall grasses.
Station Inn Pawling

Station Inn Pawling

3 out of 5
7 Memorial Avenue Pawling NY
$141 nightly
The price is $160 total per night from Nov 9 to Nov 10
$160 total
Nov 9 - Nov 10
Total with taxes and fees
Stay at this guesthouse in Pawling. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Pawling Free Library and John Kane House are located ...
9.2/10 Wonderful! (213 reviews)
"Big room, cool inn. A/C worked great."

Reviewed on Oct 5, 2026

Station Inn Pawling
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
$103 nightly
The price is $118 total per night from Oct 25 to Oct 26
$118 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,473 reviews)
"The place is very old and outdated it needs some serious renovations"

Reviewed on Oct 8, 2026

Ethan Allen Hotel
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
$94 nightly
The price is $109 total per night from Nov 9 to Nov 10
$109 total
Nov 9 - Nov 10
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! (1,111 reviews)
"The hotel is always clean. The staff is always great!"

Reviewed on Oct 9, 2026

Hyatt Place Poughkeepsie / Hudson Valley
See all 859 properties in Pawling
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.
1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen

Fishkill NY
Stay at this apartment in Fishkill. Enjoy free WiFi, cable/satellite TV service, and air conditioning. Popular attractions Van Wyck Homestead Museum and Fishkill ...
1 Queen Bed | Non-Smoking, Kitchen
Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!

Brewster NY
Enjoy air conditioning. Popular attractions Stanley Lasker Richter Memorial Park and Richter Park Golf Course are located nearby.
10/10 Exceptional! (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."

Reviewed on Jul 19, 2026

Welcome to Sweet Abby Rose!
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Carmel Hamlet NY
Stay at this vacation home in Carmel. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions ...
10/10 Exceptional! (120 reviews)
"The house is absolutely wonderful — everything you could possibly need is there, and the surroundings are so peaceful and private. There’s truly nothing more you could ask for to enjoy a perfect getaway. Everything is brand new, spotless, and beautifully maintained.Thank you so much to the host for ..."

Reviewed on Sep 20, 2026

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
See all properties in Pawling
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.

Stay near popular Pawling attractions

John Kane House

Find out about the history of Pawling with a stop at John Kane House. While in this trendy area, you can savor the top-notch restaurants.
See properties

Frequently asked questions

Is Pawling worth visiting?
Pawling is worth visiting for its standout attractions, including the historic John Kane House and live music at Daryl's House Club. Travelers can also enjoy diverse dining experiences with Asian and Italian cuisine options. Plus, getting to and from Pawling is convenient, thanks to practical train access.
When is the best time to visit Pawling?
The best time to visit Pawling is from May through September, when the weather is typically warm and pleasant. For travelers seeking fewer crowds and better value, the cooler months of December through March are a good option, offering a different seasonal atmosphere.
What is Pawling known for?
Pawling is known for its historical landmarks and entertainment venues. Travelers can explore the historic John Kane House, enjoy live music at Daryl's House Club, and visit the Akin Free Library. This city in the United States offers a blend of culture and recreation.
What is a good itinerary length for Pawling?
A good itinerary length for Pawling is one to two days to explore key attractions like the John Kane House, Daryl's House Club, and Akin Free Library. An extended stay of three to four days allows more time to enjoy the local Asian, Italian, or European cuisine, or to use the train for further exploration of the area at a relaxed pace.
How do you get around Pawling?
In Pawling, travelers can get around by train, with service available at the Appalachian Trail station. For more localized travel or to reach areas not served by the train, rideshare services are a convenient option to explore the town and its surroundings.
What are the top things to do in and around Pawling?
In Pawling, travelers can explore local landmarks and community gathering places:

  • Visit the John Kane House
  • Explore Daryl's House Club
  • See the Akin Free Library
  • Discover Pawling Village Hall
  • Tour Pawling Town Hall

How do I plan a trip to Pawling?
To plan your trip to Pawling, search for places to stay on Expedia and book activities like visiting the John Kane House, Daryl's House Club, or Akin Free Library. You can travel to Pawling by train. Remember to pair outdoor plans with indoor backups for weather flexibility, and book any flights or rental cars in advance.
What cuisines can you find in Pawling?
In Pawling you can find German cuisine, featuring dishes like bratwurst, schnitzel, pretzels, and sauerkraut. Travelers can also enjoy a variety of other options, including Asian, Italian, and Latin American flavors, alongside general European and North American fare.
Can I book a refundable hotel in Pawling?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Pawling 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 Pawling with Expedia?
Expedia makes it easier to plan your Pawling 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 Pawling?
The best choice depends on your travel style. Hotels in Pawling 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 Pawling trip on Expedia?
Once you've booked your Pawling 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 Pawling trip?
Expedia offers customer support before, during, and after your Pawling 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 Pawling?
If it's your first trip to Pawling, 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 Pawling 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 Pawling hotel.

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

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