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

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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
$511 nightly
The price is $578
Oct 13 - Oct 14
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

2. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
$170 nightly
The price is $184
Oct 4 - Oct 5
Total with taxes and fees
Welcome to Sweet Abby Rose!
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

3. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
$301 nightly
The price is $341
Oct 18 - Oct 19
Total with taxes and fees
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
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, (1 review)
"Clean and close to activitys"
United States
randall
$140 nightly
The price is $158
Oct 13 - Oct 14
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

5. 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.
$247 nightly
The price is $279
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

6. 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.
$378 nightly
The price is $410
Oct 5 - Oct 6
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A living room with a fireplace, two armchairs, a sofa, and a TV.

7. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
$188 nightly
The price is $213
Oct 5 - Oct 6
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

8. 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
$72 nightly
The price is $81
Oct 26 - Oct 27
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A multi-story house with a dock and boats, surrounded by dense forest.

9. 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.
$1,087 nightly
The price is $1,233
Oct 14 - Oct 15
Total with taxes and fees
North Cliff House - Private Dock & Sauna
A brick building with a sign reading 'Lobby' in front.

10. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.2 out of 10, Wonderful, (21 reviews)
"great place tostay"
United States
Anonymous traveler
$88 nightly
The price is $102
Oct 26 - Oct 27
Total with taxes and fees
2 Full Beds | Non-Smoking, Kitchen
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

11. 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
$708 nightly
The price is $804
Oct 5 - Oct 6
Total with taxes and fees
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A modern hotel room with a large bed, bedside tables, a desk, and a chair.

12. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
$115 nightly
The price is $132
Oct 4 - Oct 5
Total with taxes and fees
1 King Bed | Non-Smoking
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

13. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
$204 nightly
The price is $231
Oct 18 - Oct 19
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
A brick building with a sign reading 'Lobby' in front.

14. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveler
$80 nightly
The price is $92
Oct 26 - Oct 27
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Bedroom

15. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
8.4 out of 10, Very good, (25 reviews)
"Arrived with paid reservation -no rooms available......not a legit business. The sister hotel in the area had same issue earlier this year. I will not return."
United States
Cheryl
2 Queen Beds | Non-Smoking, Kitchen
A white house with a wooden staircase leading to a porch.

16. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
$106 nightly
The price is $118
Oct 14 - Oct 15
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
A brick building with a sign reading 'Lobby' in front.

17. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
8.4 out of 10, Very good, (23 reviews)
"Nice place to stay"
United States
Anonymous traveler
$80 nightly
The price is $92
Oct 26 - Oct 27
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

18. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (5 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
$367 nightly
The price is $418
Nov 1 - Nov 2
Total with taxes and fees
Rustic Cabin in Fishkill!
A hotel room with a bed, a desk, a chair, a TV, and a window with curtains.

19. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Bethel
$119 nightly
The price is $137
Oct 4 - Oct 5
Total with taxes and fees
2 Queen Beds | Non-Smoking
A modern hotel room with a large bed, a desk with a chair, a flat-screen TV, and a window with curtains.

20. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
$110 nightly
The price is $126
Oct 5 - Oct 6
Total with taxes and fees
1 Queen Bed | Non-Smoking
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pawling Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent
"very friendly helpful staff. very clean rooms. I loved the pillows. Where do you get them?"
Sharon 7-night trip
Posted 10 hours ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

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 $92 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.

Explore a world of travel with Expedia

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.