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

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Pawling vacation homes

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 $95
CA $202 total
includes taxes & fees
Nov 3 - Nov 4
Cozy private room in a shared home with a Full-size bed and private bathroom.
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

2. "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 CA $280
CA $808 total
includes taxes & fees
Nov 2 - Nov 3
"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.

3. 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 $234
CA $499 total
includes taxes & fees
Nov 3 - Nov 4
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

4. 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 $238
CA $399 total
includes taxes & fees
Oct 22 - Oct 23
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A multi-story house with a dock and boats, surrounded by dense forest.

5. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
The price is CA $492
CA $1,774 total
includes taxes & fees
Oct 26 - Oct 27
North Cliff House - Private Dock & Sauna
A bedroom with a bed, a dresser, and a window with curtains.

6. 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 $738
CA $1,224 total
includes taxes & fees
Oct 26 - Oct 27
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

7. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is CA $387
CA $596 total
includes taxes & fees
Nov 11 - Nov 12
Red Cottage - Lakeside Property!
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

8. 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 CA $541
CA $798 total
includes taxes & fees
Nov 1 - Nov 2
Hickory on Willow Lake
An outdoor patio area with a covered seating area, a pool, and potted plants.

9. 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 CA $367
CA $487 total
includes taxes & fees
Oct 28 - Oct 29
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

10. 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 CA $226
CA $614 total
includes taxes & fees
Oct 22 - Oct 23
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

11. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (7 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is CA $563
CA $1,163 total
includes taxes & fees
Oct 26 - Oct 27
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
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 CA $541
CA $798 total
includes taxes & fees
Nov 11 - Nov 12
Chestnut on Willow Lake
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

13. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is CA $382
CA $959 total
includes taxes & fees
Oct 22 - Oct 23
Renovated Retreat with Heated Pool
A hot tub in a backyard with a house, trees, and a clear sky.

14. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is CA $3,797
CA $4,929 total
includes taxes & fees
Oct 22 - Oct 23
Las Flores Villa
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

15. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
The price is CA $350
CA $779 total
includes taxes & fees
Oct 22 - Oct 23
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A staircase with red carpeted steps, wooden handrails, and string lights.

16. Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (17 reviews)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is CA $582
CA $786 total
includes taxes & fees
Nov 1 - Nov 2
Large,Cozy,Bright Apartment, Business Themed.
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

17. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is CA $633
CA $975 total
includes taxes & fees
Oct 25 - Oct 26
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
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

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"Very nice and clean property. Rooms are very comfortable and spacious. We frequent this hotel often due to the location. Would definitely stay here again,"
Amy 2-night trip
Posted 1 hour ago
Holiday Inn Express Poughkeepsie by IHG

Find out more about Pawling

Pawling Vacation Homes information

Number of reviews
161
Accommodation
241 Vacation Homes
Lowest Price
CA $202
Highest Price
CA $4,929

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