Pawling Vacation Packages

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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.
San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was CA $942, price is now CA $600 per person
CA $600
per person
Aug 2 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,828 reviews)
The bathtub was slippery and the tap was tight. I slipped and fell when trying to fix the tap and cracked a rib. The hotel just sent a bath tub mat but offered no compensation for the medical treatment i underwent in urgebnt care. They offered to fix the tap and probably fixed it.

Reviewed on Jul 2, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $6,109, price is now CA $3,795 per person
CA $3,795
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Atmosphere was amazing. Layout was incredibly unique. Will definitely be returning

Reviewed on Jul 2, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,994, price is now CA $1,277 per person
CA $1,277
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,632 reviews)
From check in to check out, was very efficient, breakfast was very good, large selection! Everyone was very helpful! Will stay here again!

Reviewed on Jul 3, 2026

The Prince Kitano New York

The Prince Kitano New York

4.5 out of 5
Manhattan
Price was CA $1,777, price is now CA $1,155 per person
CA $1,155
per person
Sep 4 - Sep 7
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (2,275 reviews)
Very clean friendly staff

Reviewed on Jul 3, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,511, price is now CA $984 per person
CA $984
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
All was good

Reviewed on Jul 3, 2026

Ready to book your vacation to Pawling?

 

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Pawling Hotel Deals

Station Inn Pawling

Station Inn Pawling

3 out of 5
7 Memorial Avenue Pawling NY
The price is CA $225 per night from Jul 5 to Jul 6
CA $225
CA $255 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (205 reviews)
"Perfect place to stay the night. You can hear the train passing by, but there are ear plugs and a white noise machine in the room. It didn't bother us at all, but it might other folks"

Reviewed on Jun 29, 2026

Station Inn Pawling
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Jul 5 to Jul 6
CA $144
CA $166 total
Jul 5 - Jul 6
includes taxes & fees
8/10 Very good! (1,277 reviews)
"Sink and tub did not drain well. Beds comfortable. Accommodations are quiet. The whole building needs an update of carpet, furnishings, paint, etc."

Reviewed on Jul 2, 2026

Ethan Allen Hotel
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Jul 12 to Jul 13
CA $183
CA $213 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"AMAZING HOTEL!! if you need a place to stay for a night or two definitely choose this one! clean, nice quality, spacious affordable room, nice bathroom, nice indoor pool a& gym and inclusive breakfast! I often go back and forth to this area so I will be back!"

Reviewed on Jun 30, 2026

Hyatt Place Poughkeepsie / Hudson Valley
See all 853 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.
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Stay near popular Pawling attractions

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?
See properties

Frequently asked questions

How much does a Pawling vacation package cost?
You'll find cheap prices from CA $600 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?

  1. Pick your dates: What you want to do in Pawling and your favourite season will help you decide when to get away.
  2. 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.
  3. 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.
  4. Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Pawling vacation package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.