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

Pawling Holiday Rentals

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Check prices for these dates

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

Our top choices for Pawling holiday 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 NZ$988
includes taxes & fees
11 Nov - 12 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.

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 NZ$601
includes taxes & fees
11 Nov - 12 Nov
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 NZ$912
includes taxes & fees
11 Nov - 12 Nov
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 NZ$235
includes taxes & fees
12 Nov - 13 Nov
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 NZ$964
includes taxes & fees
11 Nov - 12 Nov
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 NZ$967
includes taxes & fees
11 Nov - 12 Nov
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 NZ$463
includes taxes & fees
13 Nov - 14 Nov
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 NZ$326
includes taxes & fees
11 Nov - 12 Nov
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 private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is NZ$332
includes taxes & fees
11 Nov - 12 Nov
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 NZ$1,435
includes taxes & fees
12 Nov - 13 Nov
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 NZ$640
includes taxes & fees
13 Nov - 14 Nov
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 NZ$967
includes taxes & fees
11 Nov - 12 Nov
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 NZ$711
includes taxes & fees
11 Nov - 12 Nov
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 traveller
The price is NZ$225
includes taxes & fees
11 Nov - 12 Nov
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 traveller
The price is NZ$164
includes taxes & fees
27 Nov - 28 Nov
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 NZ$585
includes taxes & fees
15 Nov - 16 Nov
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 NZ$831
includes taxes & fees
11 Nov - 12 Nov
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 traveller
The price is NZ$144
includes taxes & fees
17 Nov - 18 Nov
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 NZ$967
includes taxes & fees
11 Nov - 12 Nov
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 NZ$832
includes taxes & fees
16 Nov - 17 Nov
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

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

8/10 Good
"Conveniently situated, this property offers an affordable accommodation option; a straightforward motel providing basic amenities without additional features."
Brian 1-night trip
Posted 3 hours ago
Quality Inn Poughkeepsie

Find out more about Pawling

Everything you need to know about Pawling holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pawling holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pawling holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pawling holiday rentals we have selected for you start as low as NZ$164 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 holiday 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 holiday.

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 holiday rentals in Pawling?

Yes, there are holiday rentals close to the most popular sights in Pawling, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pawling has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Pawling offers a fireplace, a patio and a BBQ 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 that 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 holiday rentals like in Pawling?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pawling. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.