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Compare Vacation Homes in Pawling with updated reviews, rates, and availability.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (62)
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Gorgeous NEW Candlewood Lake 4BR 2BA Direct Waterfront Home +Dock ~JUNE SPECIAL!
Gorgeous NEW Candlewood Lake 4BR 2BA Direct Waterfront Home +Dock ~JUNE SPECIAL!
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
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Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (21)
"The cottage house had a warm, welcoming vibe to it. It was very well maintained. The grounds were beautiful. The home had everything available that you could possibly want. It was very cozy. We had relatives from Italy with us and they absolutely loved it. I would definitely go back and I highly recommend it. Congratulations to the owners, because they have done a wonderful job with it."
Charming 1870 cape cottage in Litchfield
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (21)
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, (17)
"Gorgeous, as advertised!"
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
9.8 out of 10, Exceptional, (20)
"Several days with family for my Son’s West Point Graduation! House was perfect , located in a nice neighborhood. Hosts are super friendly and easy to communicate with. Prompt response and helpful information! Highly recommend for groups from 4-8! Thank you !"
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (59)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Spacious restored Victorian w/ wraparound porch
9.6 out of 10, Exceptional, (9)
"We enjoyed our stay very much!"
Spacious restored Victorian w/ wraparound porch
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (18)
"We had a very pleasant stay! We came for our son’s graduation from West Point. Pat was a gracious host and made sure that we had up to date info. There were lots of thoughtful amenities, the beds and couches were very comfortable, we used the grill and sat on the deck which overlooks a wooded hill. The location is peaceful and in the country just down the street from a horse pasture. You can hear the brook bubbling across the way. The WiFi worked great and although there is just a window air...
The price is $176
$319 total
includes taxes & fees
Jun 17 - Jun 18
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (17)
"The property is lovely and well prepared for guests. The location is wonderful. One of our highlights was watching a bald eagle soar over the lake."
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
The Long View of Candlewood Lake
9.8 out of 10, Exceptional, (8)
"Great location! Never found the beach passes, but it wasn't an issue. Enjoyed using the kayaks. Loved the house. Wish the primary bed was more comfortable. Could not find a toilet plunger. Enjoyed meeting Mark who briefed us on the community policies."
The Long View of Candlewood Lake
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
Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (38)
"This charming 2-bedroom New Preston apartment was the perfect escape! Cozy rooms welcomed us with peace and comfort, melting away city stress. Host Melanie's warm smile and delicious homemade cookies added a personal touch that made our stay truly heartwarming. Reconnecting with nature was easy - breathtaking scenery, quiet streets, and a nearby lake offered peaceful beauty. This wasn't just a place to stay, it was an experience we'll treasure. Highly recommend! ⭐⭐⭐⭐⭐ P.S. too bad I forgot...
Private Annex/Former Artist Studio
Litchfield County Getaway
10.0 out of 10, Exceptional, (35)
"Very nicely renovated house. Clean and comfortable. Well equipped kitchen. Large comfy living and dining room. Very responsive hosts. Only suggestion would be to provide a few more hooks in the bathrooms for guests to hang personal things (night clothes, used towels, etc.). I would highly recommended this place."
Litchfield County Getaway
Charming Sharon Dwelling w/ Deck & Fire Pit!
9.6 out of 10, Exceptional, (4)
"This is a beautiful older home and I loved its charm. The wrap around porch is so quaint. However, the listing mentioned steep staircase but not to the extent that it was actually unsafe for my elderly parents. You can literally step out of the bedroom and bathroom on the 2nd floor and tumble down the stairs as the stairs don’t match up to the doorways. There is a bedroom on the 1st floor but the bed is pushed against the all so again my mother couldn’t get out. Also there are only 2 claw foot...
Charming Sharon Dwelling w/ Deck & Fire Pit!
Enjoy pool time at our spacious home; minutes from the village of Millbrook!
9.8 out of 10, Exceptional, (45)
"Long graduation weekend with parents and two grandmothers. Location was perfect, house was in great shape and getting in touch with host was a breeze."
Enjoy pool time at our spacious home; minutes from the village of Millbrook!
Lovely Highland Home w/ Pool & Hot Tub!
9.4 out of 10, Exceptional, (3)
"I rented this house for my wife’s bridesmaids. Beautiful house."
Lovely Highland Home w/ Pool & Hot Tub!
Pet-Friendly Hopewell Junction Home w/ Pool
9.4 out of 10, Exceptional, (3)
"Good option to stay at with family"
Pet-Friendly Hopewell Junction Home w/ Pool
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (74)
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
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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.

Other property types in Pawling

Stunning Pawling Retreat w/ Ponds & Waterfall
10.0 out of 10, Exceptional, (2)
"This property is even better than the pictures. The fall colors and temperature was a perfect complement to an amazing house"
Stunning Pawling Retreat w/ Ponds & Waterfall
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (75)
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
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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