A wooden boardwalk with a wooden chair and a sign reading "Swamp River Boardwalk."

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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Pawling vacation rentals

Private kitchen

1. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
The price is ￥10,829
￥22,964 total
includes taxes & fees
Aug 14 - Aug 15
Cozy private room in a shared home with a Full-size bed and private bathroom.
Exterior

2. Sumak Kawsay - Life in harmony. Waterfront Hot Tub + NYC

Sumak Kawsay - Life in harmony. Waterfront Hot Tub + NYC
Newtown
10.0 out of 10, Exceptional, (1 review)
"What a beautiful, cozy and super well kept place. We absolutely enjoyed our stay and the place had everything we needed. My favorite part was sitting on the back deck watching the boats go by. So peaceful. The place is super close to a cute town which we didn’t have time to explore but we will be back!"
United States
Linsey B.
The price is ￥28,525
￥47,776 total
includes taxes & fees
Aug 26 - Aug 27
Sumak Kawsay - Life in harmony. Waterfront Hot Tub + NYC
Property grounds

3. Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Carmel
9.4 out of 10, Exceptional, (10 reviews)
"Such a lovely cabin - so many details to make for an incredible stay. Amazing location - lake, mountains! Wylda was wonderful."
United States
Clare
The price is ￥15,925
￥36,588 total
includes taxes & fees
Aug 13 - Aug 14
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
1 bedroom, internet, bed sheets

4. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is ￥15,925
￥29,512 total
includes taxes & fees
Aug 30 - Aug 31
Welcome to Sweet Abby Rose!
Property grounds

5. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
The price is ￥17,518
￥32,968 total
includes taxes & fees
Sep 7 - Sep 8
Hoppy Hill Farm House
Coffee/tea maker, fridge, microwave, oven

6. "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 ￥34,255
￥95,858 total
includes taxes & fees
Sep 10 - Sep 11
"Country outside the city " 3 bedrooms 2 full bathrooms
Interior

7. 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 ￥24,206
￥33,310 total
includes taxes & fees
Sep 9 - Sep 10
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Exterior

8. 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 ￥16,721
￥32,066 total
includes taxes & fees
Aug 30 - Aug 31
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Property grounds

9. Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (3 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
The price is ￥23,891
￥50,403 total
includes taxes & fees
Aug 13 - Aug 14
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Living area

10. 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 price is ￥24,684
￥50,051 total
includes taxes & fees
Sep 1 - Sep 2
The Hideaway
TV, fireplace

11. 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, (18 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥40,136
￥73,360 total
includes taxes & fees
Aug 13 - Aug 14
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor dining

12. Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
The price is ￥12,758
￥21,281 total
includes taxes & fees
Aug 17 - Aug 18
Glamping, family fun, pet friendly
Lobby

13. 1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen

1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen
Fishkill
10.0 out of 10, Exceptional, (15 reviews)
"Good so far"
United States
Anonymous traveler
The price is ￥12,965
￥14,666 total
includes taxes & fees
Sep 1 - Sep 2
1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen
Exterior

14. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is ￥11,667
￥13,489 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Smart TV, fireplace, books

15. 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, (23 reviews)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
The price is ￥31,054
￥40,171 total
includes taxes & fees
Aug 27 - Aug 28
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Exterior

16. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 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 ￥14,762
￥20,162 total
includes taxes & fees
Sep 8 - Sep 9
Cozy One Bedroom Apartment Centrally Located in Southbury
Outdoor dining

17. 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, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is ￥23,222
￥37,098 total
includes taxes & fees
Aug 25 - Aug 26
The Perch in the Purchase -- Cozy, unique, and private
Cookware/dishes/utensils

18. Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (11 reviews)
"Nicole is a wonderful host. We had a fantastic stay at her house. The home was beautifully prepared, and we felt very comfortable throughout our visit. Even though it was a rainy weekend, we were still able to enjoy the huge hot tub and had a great time playing the card games and board games provided. Thank you!!"
United States
W Y.
The price is ￥71,672
￥123,594 total
includes taxes & fees
Aug 24 - Aug 25
Awesome Lake Home with tons of fun!
Exterior detail

19. Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥27,057
￥78,912 total
includes taxes & fees
Aug 13 - Aug 14
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Outdoor dining

20. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
The price is ￥20,543
￥32,168 total
includes taxes & fees
Aug 16 - Aug 17
Cabin in the heart of the Hudson Valley, Cabin 4
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

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent
"Beutiful room great hotel amazing staff wonderful breakfast fantastic location very super nice and relaxing great experience overall Had wonderful family time"
Antoun 4-night trip
Posted 8 hours ago
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

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!

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 an electric kettle, 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 Daryl's House Club and John Kane House, whereas Edward R Murrow Park is one 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.