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Next weekend
Aug 8 - Aug 10
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Aug 15 - Aug 17
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Aug 29 - Aug 31
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Sep 26 - Sep 28

Browse Select Pawling Vacation Homes

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (26)
"Perfect for small family stay over for a wedding ! "
The price is CA $357
CA $459 total
includes taxes & fees
Aug 31 - Sep 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Serene Hudson Valley Escape w/ Pool & Grill
Fridge, microwave, stovetop, dishwasher

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (1)
"An amazing stay in the 4th of July weekend- great place, double pool, giant rooms and everything in, included a patio for chillout, grilling and enjoy weekends with family and friends. Also, owners are nice, really kind and we definitely stay in touch for future escapes"
Serene Hudson Valley Escape w/ Pool & Grill
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Cozy living room with a fireplace, flat-screen TV, and comfortable seating area.

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

9.2 out of 10, Wonderful, (35)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Enjoy a peaceful lakeside retreat with a barbecue grill and comfortable seating area.

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

9.0 out of 10, Wonderful, (17)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room
Relax by the serene pool surrounded by lush greenery and a children's play area.

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

6.0 out of 10, (1)
"Property was very clean and nicely decorated. There isn’t really a living room to hang out. Very difficult for 3 adults to all hang out together. When I booked I was more concerned about the sleeping area so I assumed there was a living room. The guest suite is in the basement of home in a nice neighborhood."
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and ample counter space.

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

10.0 out of 10, Exceptional, (85)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Private Annex/Former Artist Studio
Relax on the deck overlooking a lush garden with a tranquil atmosphere.

Private Annex/Former Artist Studio

10.0 out of 10, Exceptional, (51)
"Great property great location wonderful day"
Private Annex/Former Artist Studio
Modern NY Home w/ Views By Hudson Valley Hiking!
Relax in this stylish living space with a large sofa, matching ottoman, and modern light fixture.

Modern NY Home w/ Views By Hudson Valley Hiking!

9.8 out of 10, Exceptional, (25)
"Lovely home and great proximity to Taconic Parkway for all points north and south. Owner very accomodating"
Modern NY Home w/ Views By Hudson Valley Hiking!
Enjoy pool time at our spacious home; minutes from the village of Millbrook!
Relax by the rectangular pool surrounded by a deck and lush greenery.

Enjoy pool time at our spacious home; minutes from the village of Millbrook!

9.8 out of 10, Exceptional, (58)
"Very nice home with pleasant semi country view. Outdoor pool looked nice, but too bad it was snowing and raining during stay."
Enjoy pool time at our spacious home; minutes from the village of Millbrook!
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Enjoy a formal dining experience with a view of the surrounding forest from the large windows.

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
The House In Highland- Secluded Retreat
Enjoy outdoor dining and relaxation on the spacious deck with comfortable seating and a barbecue grill.

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (9)
The House In Highland- Secluded Retreat
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Relax by the serene lake with a dock, Adirondack chairs, and a small table.

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Hickory on Willow Lake
Escape to a serene oasis beneath a triangular gazebo, surrounded by lush greenery and a tranquil hillside setting.

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is CA $586
CA $852 total
includes taxes & fees
Aug 4 - Aug 5
Hickory on Willow Lake
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Enjoy serene lakeside views from the dock, where a rowboat and canoe await.

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

10.0 out of 10, Exceptional, (122)
"My family and I stayed at the Lake House for the holiday. We can not say enough about the amenities, the house & the owners. We look forward to returning to this magical place for our next family reunion."
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Private hidden gem walking distance to town, restaurants, and shopping!
Relax in a serene backyard oasis with a pool, lounge chairs, and dining area.

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

9.8 out of 10, Exceptional, (18)
"Great property!"
Private hidden gem walking distance to town, restaurants, and shopping!
Awesome Lake Home with tons of fun!
Relax in a hot tub surrounded by a wooden deck and a serene wooded area.

Awesome Lake Home with tons of fun!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot "
The price is CA $620
CA $1,070 total
includes taxes & fees
Aug 7 - Aug 8
Awesome Lake Home with tons of fun!
Litchfield County Getaway
Enjoy cooking in this well-equipped kitchen with a central island, oven, and stainless steel range hood.

Litchfield County Getaway

10.0 out of 10, Exceptional, (44)
"Came for the garlic festival and antique shopping. Perfect location and everything was just what we expected. If we come for garlic festival next year this is where I want to stay. "
Litchfield County Getaway
Spacious Woodbury Home w/ Pool + Hot Tub!
Relax in a warm and inviting space with a hot tub, wicker furniture, and large windows.

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very good, (3)
"Great spot and location, house was clean and enjoyable. Pool needs additional care and cleaning "
Spacious Woodbury Home w/ Pool + Hot Tub!
Twin Cedar Pond: Lovely Farmhouse w/ Sprawling Deck and Therapy Pool
Relax on the spacious deck with picturesque views of the serene lake and lush greenery.

Twin Cedar Pond: Lovely Farmhouse w/ Sprawling Deck and Therapy Pool

10.0 out of 10, Exceptional, (10)
"We had some trouble with our check in process, but the response time to fix it was quick. The hot tub was lovely, and the pool house was so fun for both the adults and the kids. There was an issue with my wife finding old kids applesauce packets behind the couch throw pillow. Other than that it was a great stay. Kids had fun on the swings and hammock."
Twin Cedar Pond: Lovely Farmhouse w/ Sprawling Deck and Therapy Pool
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
Relax on the patio with a round table and two chairs, surrounded by a white railing and overlooking a serene grassy area with trees.

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

10.0 out of 10, Exceptional, (4)
"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."
The price is CA $448
CA $858 total
includes taxes & fees
Aug 3 - Aug 4
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
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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Top Pawling Hotel Reviews

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Good place to stay"
Ana 1-night trip
Posted 21 hours ago
Quality Inn & Suites Fishkill South near I-84