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Compare 266 Vacation Homes in Pawling with updated reviews, rates, and availability.

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Charming 1870 cape cottage in Litchfield
Outdoor dining
Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (31)
"Beautiful house"
Charming 1870 cape cottage in Litchfield
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Private kitchen
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (24)
"It was a great couple of days"
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Private kitchen
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (6)
"Absolutely loved our stay! The house was cozy, comfortable, and well-equipped. The host was responsive and made sure everything was just right. Highly recommend!!"
The price is AED 1,833
AED 3,364 total
includes taxes & fees
24 Sep - 25 Sep
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
The price is AED 1,890
AED 3,738 total
includes taxes & fees
25 Sep - 26 Sep
Lakeview Estate - Chef's Kitchen - NYC Getaway
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor dining
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (39)
"We had such a great time! The views are stunning and the house has everything you need to enjoy your stay. The host Kerry was so helpful; we had a small issue with the shower and she had a plumber over within the hour to resolve it. Can’t wait to come back next summer! "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Bathroom
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (71)
"Hoyse is in a beautiful location and was very clean. The host was responsive and helpful. I would give it 5 stars if it actually had 3 bedrooms."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Majestic RiverView Estate - Breathtaking Views
View of the house (Pool not included)
Majestic RiverView Estate - Breathtaking Views
10.0 out of 10, Exceptional, (2)
"This house was beautiful and perfect for a weekend with friends. There is plenty of space for everyone to spread out and we enjoyed the scenic view from the back deck all weekend. Dan was very responsive from start to finish and we did not encounter any problems throughout our stay. I would highly recommend!"
Majestic RiverView Estate - Breathtaking Views
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Property grounds
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, (22)
"We had an absolutely fantastic stay at this lakefront property! The outdoor gathering spots are plentiful and perfect for family and friends to enjoy the beautiful surroundings. Whether it was morning coffee on one of the many decks, or simply lounging in the sun, every moment was magical. The kitchen was incredibly well-stocked with everything we needed to prepare meals, which made our stay even more convenient and enjoyable. The entire place was spotless, and it was clear that a lot of care...
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Spacious New 5-bedroom holiday house in lovely Hudson Valley
Living area
Spacious New 5-bedroom holiday house in lovely Hudson Valley
9.6 out of 10, Exceptional, (4)
"Clean, spacious, beautiful house and was a great experience!"
The price is AED 1,965
AED 2,742 total
includes taxes & fees
26 Sep - 27 Sep
Spacious New 5-bedroom holiday house in lovely Hudson Valley
The Queen City Cottage
Living area
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
Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY
Exterior
Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY
10.0 out of 10, Exceptional, (7)
"My family wanted a quiet place to stay for a few days. We did some local hiking and sightseeing. The architecture of the house is gorgeous. There were plenty of places to relax both inside and out."
Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
Front of the house
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
10.0 out of 10, Exceptional, (17)
"Very homey feeling, close to where we needed to go. Easy on and off from highway."
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
Modern, Magical Woodsy Escape 1 Hour From NYC
The Lodge in Summer full bloom!
Modern, Magical Woodsy Escape 1 Hour From NYC
10.0 out of 10, Exceptional, (13)
"This day was nothing short of amazing. The tranquility of the home, the land, the amenities, and the township was phenomenal. If you’re on the hustle all the time this is a great place to sit back relax and get in touch with yourself. Everything from the screen porch to the fire pit, The amazing surround sound created such a tranquil environment. If you’re looking to get away from the city life, this is highly recommended not to mention it is not far from the city . Everything is in very close...
Modern, Magical Woodsy Escape 1 Hour From NYC
FREE EV charger and NEMA plug! Breathtaking scenery.
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.
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
Exterior
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
2.0 star property
10.0 out of 10, Exceptional, (1)
"It is a small property but an excellent location on the lake. Kayaks and paddle boat provided were an added bonus. Owner is very responsive and helpful. Kitchen could be better equipped. Overall a very pleasant and enjoyable stay."
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
Cold Spring Mountain Retreat
Cold Spring Mountain Retreat awaits!
Cold Spring Mountain Retreat
10.0 out of 10, Exceptional, (2)
"My spouse and I really enjoyed our stay. It was spacious, private and the huge windows were incredible. I would not suggest checking in at night. The driveway going up to the house is very dark and uneven terrain, and no lights were on, in or around the house. But once we knew what the road was like, we were a lot more comfortable driving it at night. The house is very very private, which is great. You don't see anyone from the property, and being outside and listening to the trees rustling...
Cold Spring Mountain Retreat
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Beacon Area Vacation Rental with Heated Pool!
Lagrangeville Vacation Rental | 5BR | 3BA | 4,000 Sq Ft | Steps Required
Beacon Area Vacation Rental with Heated Pool!
10.0 out of 10, Exceptional, (10)
"Property worked very well for us. Pool was great. (Couple of notes: The stay listed above is slightly incorrect. We arrived on Wed Jun 26 and left on Sun June 30). We requested additional chairs for the pool area from the owner but they were never delivered."
Beacon Area Vacation Rental with Heated Pool!
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Exterior
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (22)
"Went over for the weekend and my kids loved playing in the pool! "
The price is AED 569
AED 1,088 total
includes taxes & fees
23 Oct - 24 Oct
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Don't see what you're looking for?
See all available properties in Pawling
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
Pawling Vacation Rental | 5BR | 3BA | Stairs Required for Access | 4,000 Sq Ft
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
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Private kitchen
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (6)
"Absolutely loved our stay! The house was cozy, comfortable, and well-equipped. The host was responsive and made sure everything was just right. Highly recommend!!"
The price is AED 1,833
AED 3,364 total
includes taxes & fees
24 Sep - 25 Sep
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
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.