Search Vacation Homes in Pawling

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Dec 26 - Dec 28
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Feb 13 - Feb 15

Our top choices for Pawling vacation homes

Fridge, microwave, oven, stovetop
"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.
$479 nightly
The price is $541
Dec 22 - Dec 23
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
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.
$328 nightly
The price is $355
Dec 22 - Dec 23
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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.
$228 nightly
The price is $258
Dec 23 - Dec 24
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Smart TV
Cozy Escape -Strong Wi-Fi -Prime Location

Vacation Home in Poughkeepsie

Cozy Escape -Strong Wi-Fi -Prime Location
6.8 out of 10, (5)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
United States
Andrea C.
$262 nightly
The price is $307
Dec 22 - Dec 23
Total with taxes and fees
Cozy Escape -Strong Wi-Fi -Prime Location
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Vacation Home in Poughkeepsie

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
$550 nightly
The price is $644
Jan 5 - Jan 6, 2026
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Outdoor dining
Cozy cute Relaxing home

Vacation Home in Southbury

Cozy cute Relaxing home
8.8 out of 10, Excellent, (6)
"nice quiet area"
United States
Alex V.
$294 nightly
The price is $333
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cozy cute Relaxing home
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Vacation 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.
$280 nightly
The price is $316
Jan 2 - Jan 3, 2026
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior
Country Retreat | Heated Saltwater Pool | BBQ | Fire Pit

Vacation Home in Redding

Country Retreat | Heated Saltwater Pool | BBQ | Fire Pit
10.0 out of 10, Exceptional, (2)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
$554 nightly
The price is $633
Jan 14 - Jan 15, 2026
Total with taxes and fees
Country Retreat | Heated Saltwater Pool | BBQ | Fire Pit
Interior
Large,Cozy,Bright Apartment, Business Themed.

Vacation Home in Newburgh

Large,Cozy,Bright Apartment, Business Themed.
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
$405 nightly
The price is $478
Dec 22 - Dec 23
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.
Interior
Peaceful Vintage Home with Private Pond in Redding, CT.

Vacation Home in Redding

Peaceful Vintage Home with Private Pond in Redding, CT.
2.0 star property
9.6 out of 10, Exceptional, (4)
"The house is absolutely beautiful and in a very serene location. The host was super helpful. We had a wonderful time and plan to make this our yearly gathering place for our holiday get together."
United States
Amarilis R.
$624 nightly
The price is $707
Jan 3 - Jan 4, 2026
Total with taxes and fees
Peaceful Vintage Home with Private Pond in Redding, CT.
Beach nearby, sun loungers, beach towels
Fun, Friends, and Family Lakefront Home w/Dock and Beach

Vacation Home in Mahopac

Fun, Friends, and Family Lakefront Home w/Dock and Beach
10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
$714 nightly
The price is $774
Jan 12 - Jan 13, 2026
Total with taxes and fees
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Private kitchen
Tranquil 4-bedroom house in welcoming Poughquag neighborhood

Vacation Home in Poughquag

Tranquil 4-bedroom house in welcoming Poughquag neighborhood
2.0 star property
$276 nightly
The price is $313
Jan 6 - Jan 7, 2026
Total with taxes and fees
Tranquil 4-bedroom house in welcoming Poughquag neighborhood
Cookware/dishes/utensils
Awesome Lake Home with tons of fun!

Vacation Home in New Fairfield

Awesome Lake Home with tons of fun!
2.0 star property
9.8 out of 10, Exceptional, (7)
"Great spot "
United States
Mike P.
$677 nightly
The price is $767
Dec 26 - Dec 27
Total with taxes and fees
Awesome Lake Home with tons of fun!
TV
Sunkissed Escape Bright Sunroom + Hammock Fun

Vacation Home in Poughkeepsie

Sunkissed Escape Bright Sunroom + Hammock Fun
2.0 star property
$324 nightly
The price is $376
Dec 22 - Dec 23
Total with taxes and fees
Sunkissed Escape Bright Sunroom + Hammock Fun
Exterior
Chestnut on Willow Lake

Vacation Home in Fishkill

Chestnut on Willow Lake
9.6 out of 10, Exceptional, (4)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
$615 nightly
The price is $701
Dec 22 - Dec 23
Total with taxes and fees
Chestnut on Willow Lake
Smart TV, fireplace, video games, DVD player
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Vacation Home in Carmel Hamlet

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
10.0 out of 10, Exceptional, (17)
"Fabulous property! Everything was as advertised with a great kitchen and grill. Tastefully decorated and comfortable. Great game room! "
United States
Rachel F.
$790 nightly
The price is $856
Dec 29 - Dec 30
Total with taxes and fees
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Interior
Modern Converted Barn with Hot Tub!

Vacation Home in Hyde Park

Modern Converted Barn with Hot Tub!
9.8 out of 10, Exceptional, (6)
"My family and I had a lovely stay at this property. The home and yard are beautiful, everything was clean and well appointed. We had an issue with the hot tub when we arrived and Ben called to walk us through the process of getting it back on, and sent a technician out to ensure everything was running properly. Check in and out was very easy. Would recommend a stay here! "
United States
Rachel E.
$1,041 nightly
The price is $1,091
Jan 11 - Jan 12, 2026
Total with taxes and fees
Modern Converted Barn with Hot Tub!
Property grounds
Red Cottage - Lakeside Property!

Vacation Home in Fishkill

Red Cottage - Lakeside Property!
$645 nightly
The price is $734
Dec 22 - Dec 23
Total with taxes and fees
Red Cottage - Lakeside Property!
Exterior
Hickory on Willow Lake

Vacation Home in Fishkill

Hickory on Willow Lake
9.6 out of 10, Exceptional, (5)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
$487 nightly
The price is $554
Dec 29 - Dec 30
Total with taxes and fees
Hickory on Willow Lake
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

Best Western Danbury/Bethel

Best Western Danbury/Bethel

10/10 Excellent
"Everything was good couldnt ask for better service "
Hector 1-night trip
Posted 2 days ago
Best Western Danbury/Bethel

Find out more about Pawling

Pawling Vacation Homes information

Number of reviews
151
Accommodation
283 Vacation Homes
Lowest Price
$258
Highest Price
$1,091

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