Pawling Trips (flight + hotel)

Photo by Marina Timo

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Top hotels in Pawling

Station Inn Pawling

Station Inn Pawling

3 out of 5
7 Memorial Avenue, Pawling, NY
The price is P12,494 per night from Aug 3 to Aug 4
P12,494
P14,134 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (174 reviews)
"Very clean."

Reviewed on Jul 4, 2025

Station Inn Pawling
La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

3 out of 5
116 Newtown Road, Danbury, CT
Fully refundableReserve now, pay when you stay
The price is P5,491 per night from Aug 24 to Aug 25
P5,491
P6,314 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
"It was clean"

Reviewed on Jul 30, 2025

La Quinta Inn & Suites by Wyndham Danbury
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is P6,340 per night from Aug 17 to Aug 18
P6,340
P7,362 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Easy access, cleanliness, excellent room. Very good breakfast."

Reviewed on Aug 1, 2025

Holiday Inn Express Poughkeepsie by IHG
See all 842 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.

Frequently asked questions

How much does a Pawling vacation package cost?
You'll find cheap prices on Expedia for your Pawling escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Pawling costs.
What are the cheapest months to go to Pawling?
Plan your getaway for the off-season and you're likely to score cheap Pawling vacation packages. Bear in mind that public holidays and local festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Pawling?
Generally, a handful of days is enough to tick off the major sights during your Pawling vacation. But if you'd like to have some time to unwind or take day tours, think about extending your trip.
How to find the best Pawling package deals?
Use Expedia's filters to find some great Pawling package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Pawling package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Pawling vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Pawling vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Pawling?
If you're considering a spontaneous Pawling vacation, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Pawling?

  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the type of activities available will also help you decide when to visit Pawling.
  2. Budget wisely: Besides the price of your accommodations, you should factor in other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Pawling.
  3. Work out your trip length: Consider how much time you want to spend exploring Pawling. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Combine your airfare and accommodations: After you've nailed down your 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.