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

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 AED 248
AED 528 total
includes taxes & fees
3 Nov - 4 Nov
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 AED 731
AED 2,119 total
includes taxes & fees
2 Nov - 3 Nov
"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 AED 612
AED 1,288 total
includes taxes & fees
3 Nov - 4 Nov
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 AED 621
AED 1,035 total
includes taxes & fees
22 Oct - 23 Oct
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.
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 AED 1,928
AED 3,200 total
includes taxes & fees
26 Oct - 27 Oct
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 AED 1,010
AED 1,536 total
includes taxes & fees
11 Nov - 12 Nov
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 AED 1,414
AED 2,071 total
includes taxes & fees
1 Nov - 2 Nov
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 AED 960
AED 1,258 total
includes taxes & fees
28 Oct - 29 Oct
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 AED 590
AED 1,582 total
includes taxes & fees
22 Oct - 23 Oct
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 AED 1,469
AED 3,054 total
includes taxes & fees
26 Oct - 27 Oct
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 AED 1,414
AED 2,071 total
includes taxes & fees
11 Nov - 12 Nov
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 AED 998
AED 2,479 total
includes taxes & fees
22 Oct - 23 Oct
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 AED 9,917
AED 12,874 total
includes taxes & fees
22 Oct - 23 Oct
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 AED 1,218
AED 2,418 total
includes taxes & fees
22 Oct - 23 Oct
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 AED 1,521
AED 2,039 total
includes taxes & fees
1 Nov - 2 Nov
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 AED 1,653
AED 2,530 total
includes taxes & fees
25 Oct - 26 Oct
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

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent
"Great location, plenty of parking, clean and modern room, friendly desk staff, good price"
Andrew 1-night trip
Posted 7 hours ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie