Pawling Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Pawling Vacation
Our vacation packages to Pawling give you countless opportunities to immerse yourself in new sights, sounds and flavors. And with all the travel planning taken care of, you can chill out and enjoy your city getaway in the way that you deserve. Love to explore your surroundings? Thunder Ridge Ski Resort, Whaley Lake and Lake Dutchess are just three of the top-rated places to visit during your trip to Pawling. Whoever you're taking time off with and whatever your bank balance, your dream Pawling vacation is just a few clicks away with Expedia.
Top Pawling Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane
CA $1,314
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (29 reviews)
Property was extremely conveniently located to Main Street. The pool was clean with plenty of towels. Staff was pleasant. Great overall experience.
Reviewed on Aug 11, 2026
San Carlos Hotel
Manhattan
CA $2,194
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,832 reviews)
We spent six nights here and had a wonderful time. The front desk team was efficient and friendly, and the bell service team was outstanding, especially Effarin. He went above and beyond to help us resolve an issue with a taxi driver, and the rest of the team was always at the door, ready to assist.
The hotel is beautiful, very clean, and well maintained. The rooms are spacious, and daily housekeeping kept everything in excellent condition throughout our stay.
Another great advantage is the location. There are many attractions within walking distance, and the subway is easily accessible, very convenient.
We would absolutely stay here again on our next visit and highly recommend this hotel to others.
Reviewed on Aug 17, 2026
1 Hotel Brooklyn Bridge
CA $2,926
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,012 reviews)
Amazing view of the city and rooftop pool is always a great time. Will be back again! Amazing staff and beautiful space.
Reviewed on Aug 17, 2026
Ready to book your vacation to Pawling?
Pawling Hotel Deals
Station Inn Pawling
7 Memorial Avenue Pawling NY
CA $210
CA $237 total
Aug 23 - Aug 24
includes taxes & fees
9/10 Wonderful! (206 reviews)
"There should be a microwave somewhere in the building that a guest can use"
Reviewed on Aug 14, 2026
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
CA $135
CA $156 total
Aug 23 - Aug 24
includes taxes & fees
8/10 Very good! (1,404 reviews)
"The young lady that check me in was a little rude. Check in was at 3p and I arrived at 3:15 at which time I was told that they did not have my room size available. I asked why at which she replied that by making the reservation via a third party the room is not guaranteed and that I would only be ..."
Reviewed on Aug 17, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $153
CA $177 total
Sep 7 - Sep 8
includes taxes & fees
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
Daryl's House Club
You can make plans for a show at Daryl's House Club during your trip to Pawling.
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.
Pawling Town Hall
Pawling Town Hall is just one of the places to see in Pawling, so why not enjoy the other things to explore during your travels?
Akin Free Library
Akin Free Library is just one of the places to see in Pawling, so why not enjoy the other things to explore during your travels?
Pawling Village Hall
Pawling Village Hall is just one of the places to see in Pawling, so why not enjoy the other things to explore during your travels?
Pawling Free Library
After visiting Pawling Free Library, make a plan to see the other sights and activities in Pawling.
Friends of Great Swamp
You can take time to visit Friends of Great Swamp during your travels to Pawling.
Edward R Murrow Park
Explore the great outdoors at Edward R Murrow Park, a lovely green space in Pawling.
Frequently asked questions
How much does a Pawling vacation package cost?
You'll find cheap prices from CA $1,314 on Expedia for your Pawling escape. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Pawling costs.
What are the cheapest months to go to Pawling?
The off-season is the best time to head to Pawling if you're on a budget. Another tip for scoring cheap Pawling vacation packages? Try to avoid public holidays and any major festivals.
How many days is enough for Pawling?
For a Pawling vacation, a few days will be enough to tour the best spots. Be sure to stop by Lake Dutchess — it's one of the main sights in this destination. If you're looking for more activities, think about basing yourself here and setting off on some trips from Pawling.
How to find the best Pawling package deals?
Use Expedia's filter tool to find some of the best Pawling package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Pawling package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Pawling vacation as a package?
You can enjoy significant savings on your Pawling getaway by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Pawling?
Land incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Pawling adventure.
How to plan a trip to Pawling?
- Pick your dates: What you want to do in Pawling and your favourite season will help you decide when to get away.
- Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to experiences and flights. Your accommodations will probably be the largest expense during your trip to Pawling.
- Decide how long to go for: Now that you're more familiar with Pawling, you can work out the right length of your break. Create a rough itinerary and give yourself enough time to cover everything you want to see.
- Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Pawling vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
