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Vacation Homes in Pawling

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

9.4 out of 10, Exceptional, (30)
"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

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (59)
"My family and I enjoyed our stay and their hospitality!"
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, (90)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (11)
"Very nice location and private."
The House In Highland- Secluded Retreat

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

9.6 out of 10, Exceptional, (36)
"Great place for a quiet stay"
The price is AED 1,010
AED 1,288 total
includes taxes & fees
30 Sep - 1 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

8.8 out of 10, Excellent, (23)
"We were very happy with the accommodations. The cottage was neat, clean and well kept, as was the property. All the amenities were as described. We had a great weekend and would highly recommend this lake house."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is AED 1,488
AED 2,503 total
includes taxes & fees
30 Sep - 1 Oct
Large,Cozy,Bright Apartment, Business Themed.

Hickory on Willow Lake

9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is AED 1,561
AED 2,242 total
includes taxes & fees
30 Sep - 1 Oct
Hickory on Willow Lake

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (30)
"Happy to have rebooked!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway

Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

10.0 out of 10, Exceptional, (22)
"Despite the weather we had a great time. The house is very comfortable, well a pointed, nicely updated and was spotless when we arrived. Location is good too!"
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (47)
"We really enjoyed totally this Candlewood lake house. it has a fantastic view and a large, beautiful lawn with a fire pit. The owner was a pleasure to work with and she even allowed us to check in a few hours early.The house is fully stocked with everything we needed. The views are fabulous, but if you bring your own boat, the property is at the tip of the lake and the water can be a little rough from other boats going by. "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

10.0 out of 10, Exceptional, (13)
"Beautiful location and lots of space for a large group. This rental is really about the outdoor space and activities. Would love to return!"
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

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

10.0 out of 10, Exceptional, (17)
"We had a great stay and had everything we needed!"
The price is AED 1,650
AED 3,181 total
includes taxes & fees
1 Oct - 2 Oct
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

10.0 out of 10, Exceptional, (13)
"House and property are beautiful. Everything was great!"
NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

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

10.0 out of 10, Exceptional, (23)
"Gorgeous views and comfortable stay!"
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

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 AED 1,194
AED 2,295 total
includes taxes & fees
7 Oct - 8 Oct
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

YOIN: Whispers of Tranquility, a Zen Retreat

YOIN: Whispers of Tranquility, a Zen Retreat

The Queen City Cottage

7.4 out of 10, Good, (16)
"We had a great stay! Good location and the house was very clean. Would definitely stay here again!"
The Queen City Cottage

Enjoy Sip O Sun - Hot Tub, Pizza Oven, Stunning Views, close to dining, shopping, town

10.0 out of 10, Exceptional, (3)
"Easy check in and check out, listing matched property exactly, clean, overall great stay. "
Enjoy Sip O Sun - Hot Tub, Pizza Oven, Stunning Views, close to dining, shopping, town

Candlewood Lake Retreat; Dock, Game Room & Firepit

10.0 out of 10, Exceptional, (47)
"Everything was great! Thank you!"
The price is AED 2,697
AED 5,025 total
includes taxes & fees
1 Oct - 2 Oct
Candlewood Lake Retreat; Dock, Game Room & Firepit
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