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Pawling Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Pawling holiday rentals

Exterior
Cozy One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

Cozy 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 HK$664
HK$920 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy One Bedroom Apartment Centrally Located in Southbury
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
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
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 HK$1,314
HK$2,167 total
includes taxes & fees
1 Jan - 2 Jan 2026
Cabin in the heart of the Hudson Valley, Cabin 3
1 bedroom, WiFi, bed sheets
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Apartment in Beacon

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is HK$855
HK$1,834 total
includes taxes & fees
5 Jan - 6 Jan 2026
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
3 bedrooms, iron/ironing board, travel cot, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms

Holiday 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 HK$1,462
HK$4,275 total
includes taxes & fees
5 Jan - 6 Jan 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 HK$777
HK$1,495 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hoppy Hill Farm House
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 HK$1,314
HK$2,167 total
includes taxes & fees
1 Jan - 2 Jan 2026
Cabin in the Heart of the Hudson Valley, Cabin 1
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Holiday 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 HK$1,294
HK$2,758 total
includes taxes & fees
8 Jan - 9 Jan 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 HK$1,166
HK$1,496 total
includes taxes & fees
8 Jan - 9 Jan 2026
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
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 HK$1,205
HK$2,459 total
includes taxes & fees
9 Jan - 10 Jan 2026
The Hideaway
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 HK$1,944
HK$3,016 total
includes taxes & fees
7 Jan - 8 Jan 2026
Charming 2-bedroom cabin on 25 acres with loft space and full basement
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 HK$855
HK$1,835 total
includes taxes & fees
7 Jan - 8 Jan 2026
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley

Apartment in Newburgh

Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (66)
"Such a cute place to stay"
United States
Melissa
The price is HK$1,360
HK$2,543 total
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy country efficiency in the Hudson Valley
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 HK$1,104
HK$2,084 total
includes taxes & fees
28 Jan - 29 Jan 2026
Lux APT Your home away from home.
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Holiday 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 HK$1,182
HK$1,997 total
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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 HK$1,049
HK$2,164 total
includes taxes & fees
9 Jan - 10 Jan 2026
Charming 1-bedroom apartment in Carmel with WiFi, AC
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 HK$1,515
HK$1,953 total
includes taxes & fees
19 Jan - 20 Jan 2026
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Outdoor dining
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Apartment in New Fairfield

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
10.0 out of 10, Exceptional, (34)
"Stunning property!!"
United States
Samantha
The price is HK$1,923
HK$3,354 total
includes taxes & fees
7 Jan - 8 Jan 2026
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Terrace/patio
Cozy cute Relaxing home

Holiday Home in Southbury

Cozy cute Relaxing home
8.8 out of 10, Excellent, (6)
"nice quiet area"
United States
Alex V.
The price is HK$1,399
HK$2,588 total
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy cute Relaxing home
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Holiday Home in Fishkill

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.6 out of 10, Exceptional, (50)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is HK$1,923
HK$2,475 total
includes taxes & fees
8 Jan - 9 Jan 2026
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

10/10 Excellent
"Changed room without any hassle "
Arthur 1-night trip
Posted 16 hours ago
Courtyard by Marriott Poughkeepsie

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:

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

Frequently asked questions

Are there holiday rentals in Pawling?

Yes, there are holiday rentals close to the most popular sights in Pawling, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pawling has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of 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 that 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 holiday rentals like in Pawling?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pawling. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.