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

Pawling Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Pawling vacation rentals

A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

1. "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 ￥31,427
￥86,723 total
includes taxes & fees
Nov 15 - Nov 16
"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.

2. 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 ￥29,855
￥57,125 total
includes taxes & fees
Nov 15 - Nov 16
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

3. Little Lake Cabin with Hot Tub and Fire Pit

Little Lake Cabin with Hot Tub and Fire Pit
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 ￥43,762
￥78,976 total
includes taxes & fees
Nov 16 - Nov 17
Little Lake Cabin with Hot Tub and Fire Pit
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

4. 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 ￥9,999
￥20,705 total
includes taxes & fees
Nov 17 - Nov 18
Cozy private room in a shared home with a Full-size bed and private bathroom.
A rustic cabin surrounded by a forest with a stream in the foreground.

5. Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Creek Side Cabin w/ Wood Fired Hot Tub & 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 ￥40,534
￥74,946 total
includes taxes & fees
Nov 17 - Nov 18
Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit
A two-story house with a balcony, surrounded by lush greenery.

6. Quiet Solitude with Firepit, Electric Stove & Private Deck

Quiet Solitude with Firepit, Electric Stove & Private Deck
Hopewell Junction
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Sara's place. Unfortunately due to all the rain we couldn't enjoy the outside facilities. The bedroom loft is charming and everything you need is there. Thanks for a great stay!"
United States
stephanie a.
The price is ￥28,514
￥85,466 total
includes taxes & fees
Nov 15 - Nov 16
Quiet Solitude with Firepit, Electric Stove & Private Deck
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

7. 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 ￥26,824
￥42,555 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

8. 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 ￥16,666
￥28,727 total
includes taxes & fees
Nov 13 - Nov 14
Welcome to Sweet Abby Rose!
A living room with a fireplace, two armchairs, a sofa, and a TV.

9. 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 nice, great location in town"
United States
Lisa F.
The price is ￥26,308
￥31,206 total
includes taxes & fees
Nov 13 - Nov 14
Mid Century Modern Studio w/ Full Kitchen - Newly Built
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.

10. 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, (2 reviews)
"The house was perfect for our girls weekend. It was even nicer in person."
United States
Lauren B.
The price is ￥76,186
￥127,214 total
includes taxes & fees
Nov 16 - Nov 17
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

11. 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 ￥39,629
￥56,037 total
includes taxes & fees
Dec 12 - Dec 13
Rustic Cabin in Fishkill!
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

12. 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 ￥61,107
￥81,595 total
includes taxes & fees
Nov 13 - Nov 14
Chestnut on Willow Lake
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

13. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is ￥43,648
￥63,256 total
includes taxes & fees
Nov 15 - Nov 16
Red Cottage - Lakeside Property!
A modern hotel room with a bed, bedside table, lamp, desk, and window.

14. 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 traveler
The price is ￥17,287
￥19,880 total
includes taxes & fees
Nov 16 - Nov 17
1 Queen Bed | Non-Smoking
A brick building with a sign reading 'Lobby' in front.

15. 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 traveler
The price is ￥12,500
￥14,453 total
includes taxes & fees
Nov 25 - Nov 26
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
An outdoor patio area with a covered seating area, a pool, and potted plants.

16. 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
9.2 out of 10, Wonderful, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is ￥41,466
￥51,616 total
includes taxes & fees
Nov 15 - Nov 16
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A white house with a steeply pitched roof and a small tower-like structure.

17. 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
9.8 out of 10, Exceptional, (9 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is ￥50,790
￥74,514 total
includes taxes & fees
Nov 13 - Nov 14
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

18. 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 traveler
The price is ￥11,249
￥12,726 total
includes taxes & fees
Nov 23 - Nov 24
1 King Bed | Non-Smoking, Kitchen, Shower
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

19. Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
The price is ￥61,107
￥81,595 total
includes taxes & fees
Nov 13 - Nov 14
Hickory on Willow Lake
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is ￥27,657
￥68,272 total
includes taxes & fees
Nov 16 - Nov 17
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
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

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

8/10 Good
"Nice enough place. Well maintained."
David 1-night trip
Posted less than an hour ago
Comfort Suites Fishkill near Interstate 84

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:

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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.