Pawling Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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.
$483 nightly
The price is $546
Nov 15 - Nov 16
Total with taxes and fees
"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.
$332 nightly
The price is $360
Nov 15 - Nov 16
Total with taxes and fees
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.
$427 nightly
The price is $486
Nov 16 - Nov 17
Total with taxes and fees
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.
$115 nightly
The price is $130
Nov 17 - Nov 18
Total with taxes and fees
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.
$422 nightly
The price is $481
Nov 17 - Nov 18
Total with taxes and fees
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.
$473 nightly
The price is $535
Nov 15 - Nov 16
Total with taxes and fees
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.
$227 nightly
The price is $257
Nov 13 - Nov 14
Total with taxes and fees
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
$167 nightly
The price is $181
Nov 13 - Nov 14
Total with taxes and fees
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.
$162 nightly
The price is $184
Nov 17 - Nov 18
Total with taxes and fees
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.
$703 nightly
The price is $801
Nov 16 - Nov 17
Total with taxes and fees
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
$312 nightly
The price is $355
Nov 13 - Nov 14
Total with taxes and fees
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.
$451 nightly
The price is $514
Nov 13 - Nov 14
Total with taxes and fees
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
$350 nightly
The price is $399
Nov 15 - Nov 16
Total with taxes and fees
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
$108 nightly
The price is $124
Nov 16 - Nov 17
Total with taxes and fees
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
$78 nightly
The price is $90
Nov 28 - Nov 29
Total with taxes and fees
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
$281 nightly
The price is $325
Nov 15 - Nov 16
Total with taxes and fees
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.
$414 nightly
The price is $468
Nov 13 - Nov 14
Total with taxes and fees
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
$70 nightly
The price is $80
Nov 23 - Nov 24
Total with taxes and fees
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.
$451 nightly
The price is $514
Nov 13 - Nov 14
Total with taxes and fees
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.
$355 nightly
The price is $416
Nov 16 - Nov 17
Total with taxes and fees
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.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

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

Beautiful property ! Anyone looking for wedding venue, check this place out ! When I walked in the door I was greeted and welcomed! The inside had old charm with beautiful woodworking, dining area was so charming , with white table cloths , beautiful windows i just wanted to sit there all day with a hot chocolate or a cup of tea ! The bedroom looked like it was recently redone with some beautiful older pieces of furniture but was spotless! towels were nice and thick! The bed was very very...
United States
ChrisL
Reviewed February 3, 2020
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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Pawling in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $79 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia