Pawling Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Pawling

Fridge, microwave, oven, stovetop
Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in Newburgh

9.8 out of 10, Exceptional, (14)
"We are moving to the area and found this cute place. Loved it and will stay here again. "
United States
Nicole G.
The price is HK$1,082
HK$1,875 total
includes taxes & fees
30 Nov - 1 Dec
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

10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is HK$856
HK$1,891 total
includes taxes & fees
14 Dec - 15 Dec
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Exterior
New One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is HK$736
HK$1,002 total
includes taxes & fees
4 Dec - 5 Dec
New One Bedroom Apartment Centrally Located in Southbury
Fridge, microwave, oven, stovetop
Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in Newburgh

10.0 out of 10, Exceptional, (31)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is HK$1,082
HK$1,857 total
includes taxes & fees
22 Dec - 23 Dec
Cabin in the Heart of the Hudson Valley, Cabin 1
Games room
Peaceful apartment on 3.5 acres w/ artist studio.

Apartment in Brookfield

9.6 out of 10, Exceptional, (19)
"This was a nice get away for us that was not too far away from home."
United States
Isabella M.
The price is HK$981
HK$1,507 total
includes taxes & fees
8 Dec - 9 Dec
Peaceful apartment on 3.5 acres w/ artist studio.
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Holiday Home in Carmel Hamlet

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$1,296
HK$2,762 total
includes taxes & fees
8 Dec - 9 Dec
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
3 bedrooms, iron/ironing board, travel cot, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms

Holiday Home in Holmes

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$1,596
HK$4,579 total
includes taxes & fees
15 Dec - 16 Dec
"Country outside the city " 3 bedrooms 2 full bathrooms
Exterior
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Camping in New Milford

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$1,167
HK$1,498 total
includes taxes & fees
26 Dec - 27 Dec
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
1 bedroom, WiFi, bed sheets
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Apartment in Beacon

9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is HK$918
HK$1,918 total
includes taxes & fees
14 Dec - 15 Dec
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Apartment in Carmel Hamlet

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$1,051
HK$2,167 total
includes taxes & fees
5 Dec - 6 Dec
Charming 1-bedroom apartment in Carmel with WiFi, AC
Property grounds
The Hideaway

Apartment in Brewster

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$1,206
HK$2,463 total
includes taxes & fees
29 Nov - 30 Nov
The Hideaway
Property grounds
Charming 2-bedroom cabin on 25 acres with loft space and full basement

Cabin in Hyde Park

10.0 out of 10, Exceptional, (1)
"Great communication with the host. They thought of every detail down to a bone for our dog. Property is gorgeous with plenty of room to relax, enjoy a fire, and have hours of fun in the game room. We felt super relaxed when we walked in - like being home. "
United States
Darlene D.
The price is HK$1,946
HK$3,020 total
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom cabin on 25 acres with loft space and full basement
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Holiday Home in Hopewell Junction

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$1,184
HK$2,008 total
includes taxes & fees
29 Nov - 30 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Fridge, microwave, oven, stovetop
Mid Century Modern Studio w/ Full Kitchen - Newly Built

Apartment in Kent

9.8 out of 10, Exceptional, (9)
"The studio is so fun with great amenities and a gorgeous view. "
United States
Kimberly
The price is HK$1,518
HK$1,940 total
includes taxes & fees
27 Nov - 28 Nov
Mid Century Modern Studio w/ Full Kitchen - Newly Built
TV
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Apartment in Southbury

2.0 star property
The price is HK$841
HK$1,346 total
includes taxes & fees
30 Nov - 1 Dec
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
Outdoor dining
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Apartment in New Fairfield

10.0 out of 10, Exceptional, (34)
"Beautiful apartment in a beautiful setting. "
United States
Lisa
The price is HK$1,926
HK$3,499 total
includes taxes & fees
2 Dec - 3 Dec
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Exterior
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5

Apartment in Poughkeepsie

2.0 star property
10.0 out of 10, Exceptional, (5)
"My friends and I rented this property for a long girls weekend to attend an event in the area. We liked the historical aspect of the property and Gary was an excellent host. His banana bread was amazing! We would definitely stay again. "
United States
Sara
The price is HK$1,807
HK$2,117 total
includes taxes & fees
30 Nov - 1 Dec
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5
Smart TV, fireplace, books
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Holiday Home in New Fairfield

10.0 out of 10, Exceptional, (14)
"The house worked very well for our family holiday. Very clean, had everything we needed "
United States
Audrey P.
The price is HK$2,059
HK$4,617 total
includes taxes & fees
26 Nov - 27 Nov
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Holiday Home in Poughkeepsie

10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
The price is HK$1,289
HK$4,564 total
includes taxes & fees
2 Dec - 3 Dec
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Terrace/patio
Cozy cute Relaxing home

Holiday Home in Southbury

8.8 out of 10, Excellent, (6)
"nice quiet area"
United States
Alex V.
The price is HK$1,284
HK$2,442 total
includes taxes & fees
5 Dec - 6 Dec
Cozy cute Relaxing home
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

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

10/10 Excellent
"Great stay "
Kareemah 1-night trip
Posted 1 day ago
Quality Inn Hyde Park Poughkeepsie North

Find out more about Pawling

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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 a coffee maker, 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.