Photo by Marina Timo

Holiday Homes in Pawling

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Featured Holiday Homes in Pawling

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

9.6 out of 10, Exceptional, (74)
"The house is as advertised. Good amount of room. The host was pretty communicative. No complaints from the property. Just wish they had a bigger table for group dinners"
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (15)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Spacious New 5-bedroom holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (6)
"The home was even more stunning in person and from the moment we pulled onto the block we were welcomed by its beautiful surroundings. The home was very comfortable, plenty of space and each of us were very impressed by the thoughtful layout and features. We were in town for a very special event commemorating our brothers amazing achievements and had everything we needed for a very pleasant and memorable stay. The screened in porch was an added bonus and of course, we all gravitated around the...
Spacious New 5-bedroom holiday house in lovely Hudson Valley

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (39)
"Hosts were very accommodating and are next door. Property is beautiful. The home is spacious, comfortable, extremely clean and well-stocked, and has that wonderful New England charm. Jeff provided reccos for dining and nature that proved to be perfect. We missed the autumn colors by a week or so….so may just have to go back to enjoy that next year"
Charming 1870 cape cottage in Litchfield

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (74)
"This place was a great place for us to stay on our vacation. Secluded outside of the city, and a short drive down a gravel road, it really feels that you're lost in the woods, but in a good way. If you're up to visit the Gunks, Angry Orchard, the Hudson river, love the beauty of the outdoors, and have other family or friends to visit in the area, definitely consider this home. Host was very responsive and had everything ready for us."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

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

The Queen City Cottage

7.4 out of 10, Good, (16)
"My wife and I, along with my two daughters and grandchildren stayed at the Queen City Cottage for 4 nights. We needed to add an extra day at the last minute and Marissa was very responsive and accommodating. The house was clean upon our arrival and entry was a breeze. It's a bedroom, 1.5 bath, with extra bathroom in basement in laundry room. Location wa great! Restaurants and shopping minutes away. Outdoor space was tranquil with table and chairs under covered back porch. Wifi was fine, TV had...
The Queen City Cottage

FREE EV charger and NEMA plug! Breathtaking scenery.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house with more features than we expected, clean and accommodating "
FREE EV charger and NEMA plug! Breathtaking scenery.

Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT

2.0 star property
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT

Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury

8.0 out of 10, Very good, (2)
"My husband, daughter and myself stayed at the house for a couple nights. The house was spacious, clean, had comfortable beds and was right on the lake. We loved that! Unfortunately, we arrived in the dark and the roads were a little tricky at night for our first time driving it. I know by the picture that there were some stairs to get to the house. I was thinking maybe 20 but 75? Since my husband has knee issues and I have back issues, it would have been good information to have on the...
Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury

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

10.0 out of 10, Exceptional, (11)
"This property was even more beautiful than it appeared in the photos. The wooded backyard was also spacious and lovely. We were so happy with the view of the lake and how peaceful the space was. The owners are easy to communicate with and prompt to respond. We will absolutely be going back. "
The price is AU$1,293
includes taxes & fees
26 Nov - 27 Nov
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Stay 3 Nights or Longer Until January 31 and Get 15% Off

9.8 out of 10, Exceptional, (28)
"Property and home are beautiful. The larger home on adjacent property (Sunny Day) is close and if a larger group is staying there can be loud in the tranquil setting during the day. Otherwise, the setting is beautiful and the house was perfect for our family of 6 (3 couples). We enjoyed the kayak, paddle board, fishing, evening fire pit and views from upstairs deck and downstairs patio. "
Stay 3 Nights or Longer Until January 31 and Get 15% Off

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (105)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

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

The Long View of Candlewood Lake

10.0 out of 10, Exceptional, (17)
"The house faces the lake and offers tranquil and beautiful views from most rooms. It was meticulously maintained and very attractive and comfortable. It was stocked with everything you would need to be comfortable and to feel like home. We stayed 2 nights and thoroughly enjoyed it!"
The Long View of Candlewood Lake

Fun, Friends, and Family Lakefront Home w/Dock and Beach

9.8 out of 10, Exceptional, (7)
"Had a great vacation with friends"
The price is AU$1,209
includes taxes & fees
3 Dec - 4 Dec
Fun, Friends, and Family Lakefront Home w/Dock and Beach

NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

10.0 out of 10, Exceptional, (3)
"First time booking and the place was perfect, beautiful views, real cozy vibes, and the host did a great job to attend at anything we needed "
NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

Large, Cozy, Bright Business Class Corporate Retreat

9.0 out of 10, Wonderful, (12)
"It went well for us in a one night stay."
The price is AU$980
includes taxes & fees
30 Nov - 1 Dec
Large, Cozy, Bright Business Class Corporate Retreat

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

8.8 out of 10, Excellent, (5)
"Eric’s place was cozy and clean with all amenities we needed. Bedrooms were cozy and roomy with comfortable mattresses. The full kitchen and Smart Tv rounded out a comfy, relaxed evening to drink wine and eat snacks from the nearby Stop and Shop. Unfortunately we could not use the beautiful fireplace due to the red flag warnings but it is a gorgeous focal piece! Our only issues were the directions on the VRBO site led us to a nearby property instead of the rental. We called the property...
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Hopewell Haven w/ heated pool and hot tub

9.4 out of 10, Exceptional, (10)
"This house has a lot of unique touches with furniture that clearly someone put a lot of thought and love into. The main room is much bigger than the listing pics let on. Ample space for a comfortable gathering. Highly recommended this home."
Hopewell Haven w/ heated pool and hot tub
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 property types in Pawling

Stunning Pawling Retreat w/ Ponds & Waterfall

10.0 out of 10, Exceptional, (5)
"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, (74)
"The house is as advertised. Good amount of room. The host was pretty communicative. No complaints from the property. Just wish they had a bigger table for group dinners"
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

The Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (11)
"So nice we keep coming back. Can't recommend highly enough and will be back in the spring. "
The Scenic Mansion With Breathtaking View
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.