Pawling Vacation Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Pawling vacation rentals

Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (29 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is AED 367
AED 496 total
includes taxes & fees
9 Jun - 10 Jun
Cozy One Bedroom Apartment Centrally Located in Southbury
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)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AED 826
AED 1,560 total
includes taxes & fees
3 Jun - 4 Jun
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Property grounds

Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (7 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is AED 294
AED 491 total
includes taxes & fees
2 Jun - 3 Jun
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is AED 551
AED 1,080 total
includes taxes & fees
2 Jun - 3 Jun
Cozy country efficiency in the Hudson Valley
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
The price is AED 404
AED 756 total
includes taxes & fees
7 Jun - 8 Jun
Hoppy Hill Farm House
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 AED 621
AED 1,024 total
includes taxes & fees
2 Jun - 3 Jun
Cabin in the heart of the Hudson Valley, Cabin 3
Exterior

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is AED 331
AED 383 total
includes taxes & fees
30 Jun - 1 Jul
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Smart TV

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
The price is AED 392
AED 1,341 total
includes taxes & fees
2 Jun - 3 Jun
King Bed | Private Parking | Strong WiFi
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)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is AED 621
AED 1,024 total
includes taxes & fees
7 Jun - 8 Jun
Cabin in the Heart of the Hudson Valley, Cabin 1
Exterior detail

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (57 reviews)
"Great location and quiet just like we like it. Unit was very charming."
Canada
Thomas
The price is AED 441
AED 918 total
includes taxes & fees
30 Jun - 1 Jul
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Lobby

1 Queen Bed | ADA/RI Shower/Smoking/Kitchen

1 Queen Bed | ADA/RI Shower/Smoking/Kitchen
Fishkill
10.0 out of 10, Exceptional, (15 reviews)
"Good so far"
United States
Anonymous traveler
The price is AED 331
AED 374 total
includes taxes & fees
30 Jun - 1 Jul
1 Queen Bed | ADA/RI Shower/Smoking/Kitchen
Hair dryer, towels, soap, toilet paper

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is AED 592
AED 824 total
includes taxes & fees
2 Jun - 3 Jun
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Outdoor dining

The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AED 516
AED 818 total
includes taxes & fees
15 Jun - 16 Jun
The Perch in the Purchase -- Cozy, unique, and private
Smart TV

Cozy Escape -Strong Wi-Fi -Prime Location

Cozy Escape -Strong Wi-Fi -Prime Location
Poughkeepsie
6.8 out of 10, (5 reviews)
"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.
The price is AED 347
AED 1,199 total
includes taxes & fees
15 Jun - 16 Jun
Cozy Escape -Strong Wi-Fi -Prime Location
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 AED 1,111
AED 1,669 total
includes taxes & fees
2 Jun - 3 Jun
Rustic Cabin in Fishkill!
Living area

The Hideaway

The Hideaway
Brewster
10.0 out of 10, Exceptional, (8 reviews)
"Nice, clean, comfortable place to stay. Beautiful, convenient setting. Will look to come back again some day for sure. "
United States
Kenneth M.
The Hideaway
Interior

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (4 reviews)
"Great host"
United States
Lindsey F.
The price is AED 665
AED 1,906 total
includes taxes & fees
2 Jun - 3 Jun
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is AED 559
AED 944 total
includes taxes & fees
2 Jun - 3 Jun
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Shower, towels, soap, toilet paper

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is AED 496
AED 999 total
includes taxes & fees
2 Jun - 3 Jun
Charming 1-bedroom apartment in Carmel with WiFi, AC
2 bedrooms, desk, WiFi

King Bed / Private Parking / 300mbps+ WiFi

King Bed / Private Parking / 300mbps+ WiFi
Poughkeepsie
5.0 out of 10, (2 reviews)
"Christina was extremely quick with her responses. My wife and I stayed at this place for the weekend and enjoyed the neighborhood. There's plenty to do, and the apartment is quaint and cozy. The only thing I'd change is adding a curtain to the bathroom window so people can't see you from the outside in."
United States
Jacob E.
The price is AED 303
AED 1,190 total
includes taxes & fees
8 Jun - 9 Jun
King Bed / Private Parking / 300mbps+ WiFi
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

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

8/10 Good
"This was a clean and comfortable hotel. The room was nice and had a lot of space. The beds were comfortable. The lobby was big and nice to relax. The staff were very kind. My only complaints are the shower was very high pressure - I was afraid to put my face directly in the water. Next, there is a blinking green light on an alarm/detector in the room which caused a flash every few seconds and that was annoying to someone in our party although I didn’t notice it with my eyes closed. Only about six channels worked on the tv. Good overall. Some quirks."
Jonathan 1-night trip
Posted 2 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

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?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This vacation home rental near Pawling is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

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.