Pawling Vacation Rentals

  • 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

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Pawling vacation rentals

Interior

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (47 reviews)
"Great place!"
United States
Sara B.
The price is ￥17,294
￥37,829 total
includes taxes & fees
Feb 10 - Feb 11
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Interior

Cozy & Serene Cabin with Fireplace, Ski Nearby!

Cozy & Serene Cabin with Fireplace, Ski Nearby!
Bethlehem
10.0 out of 10, Exceptional, (39 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
The price is ￥31,444
￥66,268 total
includes taxes & fees
Feb 10 - Feb 11
Cozy & Serene Cabin with Fireplace, Ski Nearby!
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (22 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is ￥13,741
￥18,947 total
includes taxes & fees
Feb 15 - Feb 16
Cozy One Bedroom Apartment Centrally Located in Southbury
Exterior

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
10.0 out of 10, Exceptional, (2 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is ￥50,310
￥77,188 total
includes taxes & fees
Feb 10 - Feb 11
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Exterior

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥47,559
￥70,139 total
includes taxes & fees
Feb 10 - Feb 11
Rustic Cabin in Fishkill!
Beach nearby, sun loungers, beach towels

Fun, Friends, and Family Lakefront Home w/Dock and Beach

Fun, Friends, and Family Lakefront Home w/Dock and Beach
Mahopac
10.0 out of 10, Exceptional, (15 reviews)
"Super convenient location :)"
United States
Sean M.
The price is ￥53,062
￥114,416 total
includes taxes & fees
Feb 10 - Feb 11
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Exterior detail

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (43 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is ￥17,609
￥37,467 total
includes taxes & fees
Feb 17 - Feb 18
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.4 out of 10, Exceptional, (59 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is ￥38,912
￥43,943 total
includes taxes & fees
Feb 10 - Feb 11
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
TV, fireplace

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
9.8 out of 10, Exceptional, (13 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is ￥27,592
￥57,506 total
includes taxes & fees
Feb 16 - Feb 17
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Fridge, microwave, oven, stovetop

Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is ￥28,928
￥82,123 total
includes taxes & fees
Feb 10 - Feb 11
Renovated Retreat with Heated Pool
Living area

The Hideaway

The Hideaway
Brewster
10.0 out of 10, Exceptional, (7 reviews)
"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 ￥24,369
￥49,754 total
includes taxes & fees
Feb 13 - Feb 14
The Hideaway
Exterior detail

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (35 reviews)
"Stunning property!!"
United States
Samantha
The price is ￥39,305
￥70,356 total
includes taxes & fees
Feb 13 - Feb 14
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Smart TV, fireplace, books

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥27,514
￥35,257 total
includes taxes & fees
Mar 2 - Mar 3
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Fridge, microwave, oven, stovetop

"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.
The price is ￥32,686
￥91,934 total
includes taxes & fees
Feb 10 - Feb 11
"Country outside the city " 3 bedrooms 2 full bathrooms
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is ￥26,570
￥43,828 total
includes taxes & fees
Feb 10 - Feb 11
Cabin in the Heart of the Hudson Valley, Cabin 1
Fridge, microwave, oven, stovetop

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (18 reviews)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
The price is ￥31,922
￥81,047 total
includes taxes & fees
Feb 10 - Feb 11
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
1 bedroom, WiFi

King Bed Private Parking Fast Internet

King Bed Private Parking Fast Internet
Poughkeepsie
The price is ￥8,647
￥40,511 total
includes taxes & fees
Feb 10 - Feb 11
King Bed Private Parking Fast Internet
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is ￥26,570
￥44,201 total
includes taxes & fees
Feb 19 - Feb 20
Cabin in the heart of the Hudson Valley, Cabin 3
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.6 out of 10, Exceptional, (4 reviews)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is ￥15,722
￥30,592 total
includes taxes & fees
Feb 19 - Feb 20
Hoppy Hill Farm House
Microwave, oven, stovetop

Serene 2-bedroom spacious apartment

Serene 2-bedroom spacious apartment
Carmel Hamlet
The price is ￥27,514
￥53,672 total
includes taxes & fees
Feb 11 - Feb 12
Serene 2-bedroom spacious apartment
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

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent
"Clean, spacious room"
Lisa 1-night trip
Posted 1 day ago
DoubleTree by Hilton Poughkeepsie Convention Center

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.