Pawling Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Pawling vacation rentals

Exterior
New One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

New One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (20)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is ￥14,035
￥19,259 total
includes taxes & fees
Jan 7 - Jan 8, 2026
New One Bedroom Apartment Centrally Located in Southbury
Game room
Peaceful apartment on 3.5 acres w/ artist studio.

Apartment in Brookfield

Peaceful apartment on 3.5 acres w/ artist studio.
9.6 out of 10, Exceptional, (20)
"This was a nice get away for us that was not too far away from home."
United States
Isabella M.
The price is ￥19,671
￥30,233 total
includes taxes & fees
Dec 26 - Dec 27
Peaceful apartment on 3.5 acres w/ artist studio.
Fridge, microwave, oven, stovetop
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Apartment in Beacon

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
10.0 out of 10, Exceptional, (46)
"Great location, so clean and comfortable. "
United States
Barbara
The price is ￥17,933
￥38,779 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cabin in Carmel

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
3.0 star property
10.0 out of 10, Exceptional, (3)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
The price is ￥31,068
￥54,989 total
includes taxes & fees
Dec 30 - Dec 31
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Fridge, microwave, oven, stovetop
Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in Newburgh

Cabin in the heart of the Hudson Valley, Cabin 3
9.8 out of 10, Exceptional, (14)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is ￥26,354
￥43,472 total
includes taxes & fees
Dec 28 - Dec 29
Cabin in the heart of the Hudson Valley, Cabin 3
Interior
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Cottage in Putnam Valley

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.8 out of 10, Exceptional, (23)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥46,439
￥100,110 total
includes taxes & fees
Dec 26 - Dec 27
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Microwave, oven, stovetop, dishwasher
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Apartment in Southbury

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is ￥17,754
￥29,824 total
includes taxes & fees
Dec 29 - Dec 30
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
3 bedrooms, iron/ironing board, travel crib, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms

Vacation Home in Holmes

"Country outside the city " 3 bedrooms 2 full bathrooms
2.0 star property
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is ￥29,366
￥84,437 total
includes taxes & fees
Jan 5 - Jan 6, 2026
"Country outside the city " 3 bedrooms 2 full bathrooms
Outdoor dining
Hoppy Hill Farm House

Apartment in Dover Plains

Hoppy Hill Farm House
9.6 out of 10, Exceptional, (4)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is ￥15,612
￥30,378 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hoppy Hill Farm House
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Apartment in Carmel Hamlet

Charming 1-bedroom apartment in Carmel with WiFi, AC
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is ￥21,052
￥43,433 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Charming 1-bedroom apartment in Carmel with WiFi, AC
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Vacation Home in Carmel Hamlet

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is ￥25,964
￥55,346 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Exterior
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Camping in New Milford

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
1.0 star property
8.0 out of 10, Very Good, (1)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is ￥23,391
￥30,018 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
Fridge, microwave, oven, stovetop
Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in Newburgh

Cabin in the Heart of the Hudson Valley, Cabin 1
10.0 out of 10, Exceptional, (31)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is ￥26,354
￥43,841 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cabin in the Heart of the Hudson Valley, Cabin 1
Property grounds
Charming 2-bedroom cabin on 25 acres with loft space and full basement

Cabin in Hyde Park

Charming 2-bedroom cabin on 25 acres with loft space and full basement
10.0 out of 10, Exceptional, (3)
"Beautiful house, very cozy, plenty of stuff to keep the kids busy and Zack was very helpful with everything."
United States
James S.
The price is ￥38,985
￥60,508 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Charming 2-bedroom cabin on 25 acres with loft space and full basement
Fridge, microwave, oven, stovetop
Lux APT Your home away from home.

Apartment in Beacon

Lux APT Your home away from home.
10.0 out of 10, Exceptional, (2)
"Very clean and great place to stay. "
United States
Charlene D.
The price is ￥22,143
￥42,515 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Lux APT Your home away from home.
1 bedroom, WiFi, bed sheets
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Apartment in Beacon

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is ￥17,153
￥36,803 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Property grounds
The Hideaway

Apartment in Brewster

The Hideaway
10.0 out of 10, Exceptional, (6)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
United States
Rick C.
The price is ￥24,171
￥49,349 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Hideaway
Fridge, microwave, oven, stovetop
Mid Century Modern Studio w/ Full Kitchen - Newly Built

Apartment in Kent

Mid Century Modern Studio w/ Full Kitchen - Newly Built
9.8 out of 10, Exceptional, (10)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥30,408
￥38,868 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Vacation Home in Hopewell Junction

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is ￥23,718
￥40,592 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
TV, fireplace
1 Br Private Victorian Apt in convenient City location on half acre sleeps 4

Apartment in Poughkeepsie

1 Br Private Victorian Apt in convenient City location on half acre sleeps 4
10.0 out of 10, Exceptional, (4)
"Very clean and host was very attentive. "
United States
Fabricio C.
1 Br Private Victorian Apt in convenient City location on half acre sleeps 4
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pawling Hotel Reviews

Hampton Inn Danbury

Hampton Inn Danbury

10/10 Excellent
"The staff was incredibly nice. From check in to check out. Breakfast was delicious. It was well and everything was very clean. Our family loved the pool and the hot tub."
Kathleen 2-night trip
Posted 1 day ago
Hampton Inn Danbury

Find out more about Pawling

Search for holiday rentals in Pawling on Expedia! You can easily find your home rentals, villas, holiday apartments in Pawling using one of the methods below:

  • View our selection of featured holiday rentals in Pawling
  • Use the map to find apartments and other holiday homes in the Pawling neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pawling while they last

Look no further and take a look at our great range of rental properties in Pawling!

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental near Pawling offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, 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, whereas Edward R Murrow Park is a 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.