Pawling Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,013, price is now CA $1,140 per person
CA $1,140
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $3,020, price is now CA $1,759 per person
CA $1,759
per person
Dec 20 - Dec 24
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,777, price is now CA $2,969 per person
CA $2,969
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

Le Meridien New York, Central Park by Marriott

Le Meridien New York, Central Park by Marriott

4 out of 5
Manhattan
Price was CA $3,486, price is now CA $2,177 per person
CA $2,177
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very good! (1,001 reviews)

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was CA $2,592, price is now CA $1,647 per person
CA $1,647
per person
Dec 23 - Dec 28
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.4/10 Very good! (1,813 reviews)

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 $206 per night from Dec 7 to Dec 8
CA $206
CA $233 total
Dec 7 - Dec 8
includes taxes & fees
9.2/10 Wonderful! (217 reviews)
"Tidy small inn and very comfortable. Coffee and tea were available at a station in the hall as well as in each room. Easy to come and go. Small restaurants and coffee shop are within easy walking distance."

Reviewed on Oct 31, 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 $142 per night from Dec 6 to Dec 7
CA $142
CA $164 total
Dec 6 - Dec 7
includes taxes & fees
8/10 Very good! (1,551 reviews)
"This was not what was expected when booking here. We were met with every single seam of wallpaper separated all over the room. The"

Reviewed on Nov 8, 2026

Ethan Allen Hotel
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Nov 15 to Nov 16
CA $137
CA $157 total
Nov 15 - Nov 16
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Staff was very polite and meeting our needs. Breakfast was ok. Bed was comfortable. Property needs upgrades. Was travelling for a family event, so overall the stay met our needs."

Reviewed on Nov 6, 2026

Best Western Danbury/Bethel
See all 849 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

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

How much does a Pawling vacation package cost?
You'll find cheap prices from CA $1,140 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.

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