A wooden boardwalk with a wooden chair and a sign reading "Swamp River Boardwalk."

Pawling Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Pawling vacation rentals

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

1. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
$128 nightly
The price is $144
Nov 3 - Nov 4
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

2. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
$510 nightly
The price is $577
Nov 2 - Nov 3
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

3. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"
United States
Fernanda
$170 nightly
The price is $184
Oct 22 - Oct 23
Total with taxes and fees
Welcome to Sweet Abby Rose!
A wooden deck with a lounge chair and a table, a small wooden house with a door and windows, and a wooden fence.

4. Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Carmel
9.0 out of 10, Wonderful, (13 reviews)
"Perfect little getaway, adorable space and wonderfully accommodating hosts."
United States
Susan
$230 nightly
The price is $249
Oct 22 - Oct 23
Total with taxes and fees
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

5. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$324 nightly
The price is $351
Nov 3 - Nov 4
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

6. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
$249 nightly
The price is $282
Oct 22 - Oct 23
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A living room with a fireplace, two armchairs, a sofa, and a TV.

7. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
$220 nightly
The price is $249
Oct 29 - Oct 30
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

8. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (6 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
$505 nightly
The price is $572
Oct 26 - Oct 27
Total with taxes and fees
The Little Lake Cabin with hot tub
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

9. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$79 nightly
The price is $89
Nov 18 - Nov 19
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A rustic cabin surrounded by a forest with a stream in the foreground.

10. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
$559 nightly
The price is $633
Oct 28 - Oct 29
Total with taxes and fees
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A brick building with a sign reading 'Lobby' in front.

11. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveler
$79 nightly
The price is $91
Nov 18 - Nov 19
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A multi-story house with a dock and boats, surrounded by dense forest.

12. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
$1,114 nightly
The price is $1,262
Oct 26 - Oct 27
Total with taxes and fees
North Cliff House - Private Dock & Sauna
A vending machine with various snacks and drinks.

13. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
$114 nightly
The price is $131
Nov 17 - Nov 18
Total with taxes and fees
1 King Bed | Non-Smoking
A bedroom with a bed, a dresser, and a window with curtains.

14. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
$767 nightly
The price is $871
Oct 26 - Oct 27
Total with taxes and fees
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A brick building with a sign reading 'Lobby' in front.

15. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
7.8 out of 10, Good, (26 reviews)
"The property was clean and pet friendly. However, the small extended stay room with a kitchen had no glasses or bowls or flat ware. You can't expect any additional accomodations beyond the room."
United States
Ray
$79 nightly
The price is $91
Nov 18 - Nov 19
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

16. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
$210 nightly
The price is $238
Oct 28 - Oct 29
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

17. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean rooms, Diner down the block, family friendly, communication was prompt and clear"
United States
Joseph
$340 nightly
The price is $387
Nov 6 - Nov 7
Total with taxes and fees
Rustic Cabin in Fishkill!
A brick building with a sign reading 'Lobby' in front.

18. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.0 out of 10, Wonderful, (22 reviews)
"great place tostay"
United States
Anonymous traveler
$87 nightly
The price is $101
Nov 18 - Nov 19
Total with taxes and fees
2 Full Beds | Non-Smoking, Kitchen
Bedroom

19. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
8.4 out of 10, Very good, (26 reviews)
"Arrived with paid reservation -no rooms available......not a legit business. The sister hotel in the area had same issue earlier this year. I will not return."
United States
Cheryl
$87 nightly
The price is $98
Nov 18 - Nov 19
Total with taxes and fees
2 Queen Beds | Non-Smoking, Kitchen
A hotel room with a bed, a desk with a chair, a television, and a window with curtains.

20. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Bethel
$119 nightly
The price is $137
Nov 17 - Nov 18
Total with taxes and fees
2 Queen Beds | Non-Smoking
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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Top Pawling Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent
"Great location, plenty of parking, clean and modern room, friendly desk staff, good price"
Andrew 1-night trip
Posted 3 hours ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

Find out more about Pawling

Everything you need to know about Pawling vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pawling vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pawling vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pawling vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pawling. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pawling in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $89 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pawling rentals

At Expedia, we put the best Pawling vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pawling rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pawling vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pawling. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Pawling?

Yes, we offer vacation rentals near well known points of interest in Pawling, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Pawling?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental near Pawling offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Pawling?

Cultural attractions include John Kane House and Daryl's House Club, whereas Edward R Murrow Park is one spot to enjoy nature. Other places in town to visit include Pawling Free Library and Pawling Village Hall.

What are vacation rentals like in Pawling?

Vacation rentals are private accommodations you can stay in for several days or more in Pawling. Vacation rentals offer extras such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips or small group gatherings.