Photo by Marina Timo

Pawling Holiday Rentals

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Holiday Rentals in Pawling

Stunning Pawling Retreat w/ Ponds & Waterfall

10.0 out of 10, Exceptional, (6)
"We truly enjoyed our stay at this home. It was a great gathering place for our large family to all be together and still have lots of room and be comfortable . We hope to come again to stay again! "
Stunning Pawling Retreat w/ Ponds & Waterfall

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (79)
"Thank you for allowing us to reside at your beautiful property. We appreciate your expedited communication & commitment to quality. We thank Jehovah for a safe enjoyable trip & as we return back to Atlanta, GA. "
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

10.0 out of 10, Exceptional, (15)
"Beautiful property— even more than the pictures (which is often rare). Quiet, scenic, and spacious. Communication with the host was very good and helpful."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.8 out of 10, Exceptional, (21)
"Gorgeous home and property, loved being on the lake with the game room cabana, the outdoor areas are so relaxing, and the home is so tastefully decorated. We enjoyed it so much!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (19)
"great chic house, very clean"
Cozy & Chic Cabin by the Lake, with access to private Beach!

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

10.0 out of 10, Exceptional, (53)
"The view was so good I never turned the TV on once during my stay! I was in town for a wedding and having such a clean, comfy, convenient, and well-apportioned accommodation only added to the joy of the occasion. This is an add-on to the host's residence and it was a comfort to know they were nearby while I was able to enjoy my complete privacy. "
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (27)
"The view in the fall was amazing! So relaxing to sit and watch the lake while having our coffee. The owners are amazing. Everything we needed and more. Plenty of room for the family or even if multiple families stayed. Would stay here again!"
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (7)
"We had a wonderful time in this beautiful home with lots of room and amenities!"
The price is AU$1,113
includes taxes & fees
6 Jan - 7 Jan
Spacious New Luxurious holiday house in lovely Hudson Valley

Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (87)
"The parking situation was a bit tricky because there was no good way to back in. Other than that, location was great - cute area! "
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

The Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (13)
"This house is so grand and perfect for a destination wedding, corprate retreat or family reunion. Host was wonderful!"
The Scenic Mansion With Breathtaking View

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.0 out of 10, Wonderful, (32)
"We enjoyed our stay however, the listing states all the beds are king sized and only 2 are. The other 2 are queen. Also (note for host) we forgot a pair of sunglasses and would like to have them mailed back if they are found, could you contact me if possible."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Cabin in the heart of the Hudson Valley, Cabin 4

8.8 out of 10, Excellent, (18)
"The description of the property was accurate; however, a few things surprised me that would have affected my decision to book or not. First, the house is located beside a busy road where traffic is moving all hours of the day and night at 35-55 mph. For some, this isn't a big deal. For others, it's not as quiet as described. Thankfully, I was delighted to see the room provided a noise machine. Secondly, there is no fan. Only the A/C and heater provided any air movement if you didn't want the...
The price is AU$267
includes taxes & fees
5 Jan - 6 Jan
Cabin in the heart of the Hudson Valley, Cabin 4

Majestic RiverView Estate - Breathtaking Views

10.0 out of 10, Exceptional, (4)
"We booked a weekend away to celebrate family birthdays and were very happy to celebrate in such a special place. There was plenty of room for 11 of us (+ dog) and was a mix of modern touches and old world charm highlighting the legacy of the house. And the view of the Hudson was a highlight of our stay. Highly recommend!"
Majestic RiverView Estate - Breathtaking Views

Private hidden gem walking distance to town, restaurants, and shopping!

9.8 out of 10, Exceptional, (14)
"It was very nice and relaxing . Close to everything. "
Private hidden gem walking distance to town, restaurants, and shopping!

Traveling Nurse or Business Professional

10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional

Cozy Cottage Getaway, Grill, Walk to Lake

9.6 out of 10, Exceptional, (15)
"My husband and I were very happy with our stay here. Sara was a communicative and flexible host, even before we arrived. The place matched our expectations from the listing. The cottage was clean, comfortable and had everything we needed for our multiple day stay. "
The price is AU$658
includes taxes & fees
4 Jan - 5 Jan
Cozy Cottage Getaway, Grill, Walk to Lake

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (13)
"Beautiful modern home with great views over the pond and woods. Super comfortable and many amenities. I really appreciated how well stocked the kitchen was with pots and pans that you can actually cook with compared to most VRBO's. Only drawback is that the area isn't really walkable. Busy road with minimal shoulder and you can't get down to the pond. We drove to a number of great hikes in the area though. Bonus: the woods behind the house were home to a couple great horned owls calling to...
The price is AU$1,379
includes taxes & fees
8 Jan - 9 Jan
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Candlewood Lake Retreat with year round views

10.0 out of 10, Exceptional, (10)
"Liked outdoor area and fire place "
Candlewood Lake Retreat with year round views

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

10.0 out of 10, Exceptional, (78)
"Very large house just like the photos. Host is present and responsive. We had the entire property to ourselves. Nice yard for some whiffle ball and outdoor activities. Swimming is possible at the public lake access which is about a mile away or so. Overall, a very nice stay at a very nice property. We were 10 adults (friends weekend) and fit just fine. "
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
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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Other types of properties in Pawling you may be interested in

Station Inn Pawling

3.0 star property
9.0 out of 10, Wonderful, (158)
"Everything was generally good. Station Inn is very nice and clean. The only thing I would say if you’re sensitive to noise, stay somewhere else. Train goes by a lot with the horn and the wall HVAC is loud. "
The price is AU$357
includes taxes & fees
1 Feb - 2 Feb
Station Inn Pawling

Hotel Zero Degrees Danbury

4.0 star property
9.0 out of 10, Wonderful, (1004)
"beautiful "
The price is AU$313
includes taxes & fees
4 Jan - 5 Jan
Hotel Zero Degrees Danbury

HYATT house Fishkill/Poughkeepsie

3.0 star property
8.8 out of 10, Excellent, (1007)
"We stayed so that my kids could swim. Everyone had a blast. Everyone working was so nice and helpful. Good night sleep and good breakfast "
The price is AU$179
includes taxes & fees
30 Jan - 31 Jan
HYATT house Fishkill/Poughkeepsie
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.

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, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock: This holiday home rental outside of Pawling is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Pawling?

Choose from 3 Expedia holiday rentals in Pawling for a memorable holiday.

What can I see and do in Pawling?

While exploring the area, visit family-friendly sights like SplashDown Beach, or get outside and enjoy nature at Whaley Lake. Other places in town to visit include John Kane House and Akin Free Library.

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.