Pawling Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Pawling vacation rentals

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

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
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is CA $88
CA $183 total
includes taxes & fees
Nov 9 - Nov 10
Cozy private room in a shared home with a Full-size bed and private bathroom.
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

2. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
7.4 out of 10, Good, (3 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"
United States
Fernanda
The price is CA $147
CA $255 total
includes taxes & fees
Nov 11 - Nov 12
Welcome to Sweet Abby Rose!
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

3. "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, (5 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is CA $278
CA $736 total
includes taxes & fees
Nov 11 - Nov 12
"Country outside the city " 3 bedrooms 2 full bathrooms
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

4. 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
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is CA $233
CA $473 total
includes taxes & fees
Nov 12 - Nov 13
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A living room with a fireplace, two armchairs, a sofa, and a TV.

5. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is CA $209
CA $258 total
includes taxes & fees
Nov 9 - Nov 10
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

6. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is CA $237
CA $377 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A hotel room with a bed, two bedside lamps, a nightstand, and a wall-mounted phone.

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is CA $111
CA $128 total
includes taxes & fees
Nov 25 - Nov 26
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A rustic cabin surrounded by a forest with a stream in the foreground.

8. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is CA $437
CA $757 total
includes taxes & fees
Nov 16 - Nov 17
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

9. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (7 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is CA $420
CA $720 total
includes taxes & fees
Nov 9 - Nov 10
The Little Lake Cabin with hot tub
A modern hotel room with a bed, bedside table, lamp, desk, and window.

10. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (4 reviews)
"Quick check-in and a quiet room made sleeping easy here. Everything felt straightforward without hassle."
United States
Anonymous traveller
The price is CA $153
CA $177 total
includes taxes & fees
Nov 11 - Nov 12
1 Queen Bed | Non-Smoking
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

11. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is CA $100
CA $113 total
includes taxes & fees
Nov 22 - Nov 23
1 King Bed | Non-Smoking, Kitchen, Shower
A living room with a white sectional sofa, a dining area with a wooden table and chairs, and a staircase leading to an upper level.

12. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is CA $701
CA $1,159 total
includes taxes & fees
Dec 3 - Dec 4
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A brick building with a sign reading 'Lobby' in front.

13. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.0 out of 10, Wonderful, (22 reviews)
"great place tostay"
United States
Anonymous traveller
The price is CA $122
CA $141 total
includes taxes & fees
Nov 26 - Nov 27
2 Full Beds | Non-Smoking, Kitchen
A modern hotel room with a bed, bedside table, lamp, desk, and window.

14. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (3 reviews)
"We found plenty of space for our small group plus pets. Loved having a private bathroom,it made mornings smooth."
United States
Anonymous traveller
The price is CA $160
CA $184 total
includes taxes & fees
Nov 11 - Nov 12
1 King Bed | Non-Smoking
A brick building with a sign reading 'Lobby' in front.

15. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
7.8 out of 10, Good, (26 reviews)
"The property was clean and pet friendly. However, the small extended stay room with a kitchen had no glasses or bowls or flat ware. You can't expect any additional accomodations beyond the room."
United States
Ray
The price is CA $111
CA $128 total
includes taxes & fees
Nov 25 - Nov 26
1 Queen Bed | Non-Smoking, Kitchen
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

16. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean rooms, Diner down the block, family friendly, communication was prompt and clear"
United States
Joseph
The price is CA $352
CA $507 total
includes taxes & fees
Nov 13 - Nov 14
Rustic Cabin in Fishkill!
A hotel room with two beds, a desk, a chair, and a large window with curtains.

17. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (2 reviews)
"Got a good rest before the drive. Place was clean with a refreshing shower and calm enough for sleep."
United States
Anonymous traveller
The price is CA $167
CA $192 total
includes taxes & fees
Nov 11 - Nov 12
2 Queen Beds | Non-Smoking
A white house with a wooden staircase leading to a porch.

18. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
The price is CA $145
CA $184 total
includes taxes & fees
Dec 2 - Dec 3
Cozy One Bedroom Apartment Centrally Located in Southbury
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

19. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"
United States
Quintina R.
The price is CA $540
CA $756 total
includes taxes & fees
Nov 11 - Nov 12
Chestnut on Willow Lake
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

20. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is CA $385
CA $564 total
includes taxes & fees
Nov 11 - Nov 12
Red Cottage - Lakeside Property!
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

A large white building with green shutters, a covered patio with red umbrellas, and a well-maintained garden.
Le Chambord at Curry Estate

Le Chambord at Curry Estate

Le Chambord at Curry Estate
Hopewell Junction

10/10 Excellent

The rooms are large. Everything was very clean. The breakfast has fresh fruit and a variety of baked goods. Very interesting place. We would come back.
Canada
Angela
Reviewed May 20, 2026
Le Chambord at Curry Estate

Find out more about Pawling

Everything you need to know about Pawling vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pawling vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pawling vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pawling vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pawling. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pawling vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pawling vacation rentals we have selected for you start as low as CA $88 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pawling rentals

At Expedia, we put the best Pawling vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pawling rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pawling vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pawling. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental near Pawling offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable 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. 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 and Daryl's House Club, 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.