Pawling Holiday Rentals

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Holiday Rentals in Pawling

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is AU$199
includes taxes & fees
5 Dec - 6 Dec
New One Bedroom Apartment Centrally Located in Southbury

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Beacon
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is AU$376
includes taxes & fees
14 Dec - 15 Dec
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Cozy Cottage with Grill | Walk to Lake

Putnam Valley
9.8 out of 10, Exceptional, (22)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is AU$778
includes taxes & fees
30 Nov - 1 Dec
Cozy Cottage with Grill | Walk to Lake

Cabin in the heart of the Hudson Valley, Cabin 3

Newburgh
9.8 out of 10, Exceptional, (14)
"We are moving to the area and found this cute place. Loved it and will stay here again. "
United States
Nicole G.
The price is AU$434
includes taxes & fees
30 Nov - 1 Dec
Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the Heart of the Hudson Valley, Cabin 1

Newburgh
10.0 out of 10, Exceptional, (31)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is AU$430
includes taxes & fees
1 Dec - 2 Dec
Cabin in the Heart of the Hudson Valley, Cabin 1

The Little Lake Cabin with hot tub

New Fairfield
10.0 out of 10, Exceptional, (1)
"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 Little Lake Cabin with hot tub

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Beacon
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is AU$381
includes taxes & fees
14 Dec - 15 Dec
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Peaceful apartment on 3.5 acres w/ artist studio.

Brookfield
9.6 out of 10, Exceptional, (20)
"This was a nice get away for us that was not too far away from home."
United States
Isabella M.
The price is AU$299
includes taxes & fees
30 Nov - 1 Dec
Peaceful apartment on 3.5 acres w/ artist studio.

"Country outside the city " 3 bedrooms 2 full bathrooms

2.0 star property
Holmes
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is AU$910
includes taxes & fees
15 Dec - 16 Dec
"Country outside the city " 3 bedrooms 2 full bathrooms

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

New Fairfield
10.0 out of 10, Exceptional, (16)
"The house worked very well for our family holiday. Very clean, had everything we needed "
United States
Audrey P.
The price is AU$759
includes taxes & fees
3 Dec - 4 Dec
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Carmel Hamlet
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is AU$546
includes taxes & fees
30 Nov - 1 Dec
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

1.0 star property
New Milford
8.0 out of 10, Very good, (1)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is AU$297
includes taxes & fees
30 Nov - 1 Dec
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Charming 2-bedroom cabin on 25 acres with loft space and full basement

Hyde Park
10.0 out of 10, Exceptional, (1)
"Great communication with the host. They thought of every detail down to a bone for our dog. Property is gorgeous with plenty of room to relax, enjoy a fire, and have hours of fun in the game room. We felt super relaxed when we walked in - like being home. "
United States
Darlene D.
The price is AU$591
includes taxes & fees
30 Dec - 31 Dec
Charming 2-bedroom cabin on 25 acres with loft space and full basement

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Kent
9.8 out of 10, Exceptional, (9)
"The studio is so fun with great amenities and a gorgeous view. "
United States
Kimberly
The price is AU$388
includes taxes & fees
9 Dec - 10 Dec
Mid Century Modern Studio w/ Full Kitchen - Newly Built

The Hideaway

Brewster
10.0 out of 10, Exceptional, (6)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
United States
Rick C.
The price is AU$489
includes taxes & fees
30 Nov - 1 Dec
The Hideaway

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

New Fairfield
10.0 out of 10, Exceptional, (34)
"Beautiful apartment in a beautiful setting. "
United States
Lisa
The price is AU$694
includes taxes & fees
1 Dec - 2 Dec
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

2.0 star property
Southbury
The price is AU$264
includes taxes & fees
30 Nov - 1 Dec
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Charming 1-bedroom apartment in Carmel with WiFi, AC

Carmel Hamlet
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is AU$428
includes taxes & fees
30 Nov - 1 Dec
Charming 1-bedroom apartment in Carmel with WiFi, AC

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Cornwall
10.0 out of 10, Exceptional, (5)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is AU$783
includes taxes & fees
10 Dec - 11 Dec
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is AU$402
includes taxes & fees
30 Nov - 1 Dec
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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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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 favourite 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 depend 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 AU$308 per night. Entering your travel dates in the search wizard might find you 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Pawling offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and a coffee maker, 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, whereas Edward R Murrow Park is a 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.