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Compare 61 Cottages in Pawling with updated reviews, rates, and availability.

Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Private Beach 100 yards from Cottage
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (82)
"Property was clean, well appointed, wish we could have stayed a bit longer to enjoy more of the lake & fire pit! "
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Two Bedroom Cottage Close To Town
Exterior
Two Bedroom Cottage Close To Town
9.6 out of 10, Exceptional, (17)
"What a wonderful time we had in this beautiful cottage! The property is so idyllic and perfect for a country getaway. We couldn’t ask for more in this home & needed for nothing. The beds were comfortable and the decor was just beautiful! The property owners were so friendly and very presponsive to any questions we had. We were staying in the area because it is close to Lime Rock Park, where my son was racing. We will definitely be back to stay in this wonderful cottage! Thank you for opening...
Two Bedroom Cottage Close To Town
Dreamy Hudson Valley Cottage w/ State Park Views
Garrison Vacation Rental | 1BR | 1BA | 650 Sq Ft | Steps Required
Dreamy Hudson Valley Cottage w/ State Park Views
9.6 out of 10, Exceptional, (9)
"Very clean and modern home, surrounded by woods. 15-30 minute drive from amazing hikes, lakes and cultural events. Hosts were very responsive and left nice little touches like snacks and bug spray! Would definitely stay there again."
Dreamy Hudson Valley Cottage w/ State Park Views
Idillic summer getaway in Litchfield Hills, CT.
Property grounds
Idillic summer getaway in Litchfield Hills, CT.
10.0 out of 10, Exceptional, (12)
"The property was lovely and the property manager was very friendly and accommodating. The space was ample, beds were very comfortable, and the a/c kept us cool in the middle of a heat wave. Only issue was that the house had a very musty smell to it. Also, the coffee pot was filled with old coffee-apparently they forgot to clean it prior to our arrival. Otherwise a great stay!"
Idillic summer getaway in Litchfield Hills, CT.
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
Property grounds
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
9.8 out of 10, Exceptional, (8)
"This adorable tiny home was a perfect fit for our visit to Beacon. New and nicely decorated, it had everything we could need. The shower is a "show-stopper"! Very short walking distance to Main Street, coffee shops, restaurants and a grocery store. Very pleased with our stay!"
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
Putnam Valley Vacation Rental: Patio & Lake Views!
Putnam Valley Vacation Rental | 3BR | 2BA | 7 Steps Required to Enter
Putnam Valley Vacation Rental: Patio & Lake Views!
9.6 out of 10, Exceptional, (9)
"Beautiful home and very clean. Location was a little difficult to get to but was in a nice and quiet neighborhood."
Putnam Valley Vacation Rental: Patio & Lake Views!
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Property grounds
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
9.6 out of 10, Exceptional, (14)
"Landscaping was spectacular and we enjoyed a beautiful view of the lake. Baths and bedrooms very clean. Plenty of charging ports. Terrible mold and mildew smell in lower level. Number of hazards noted, handrail missing on stairs, no lights on outdoor stairway, thermostat access by leaning over the stairs. The property needs a good deep cleaning."
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Exterior
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
10.0 out of 10, Exceptional, (4)
"The owners freshly love this place"
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Cozy 2-bedroom Cottage with Access to Bantam Lake
Cozy 2-bedroom Cottage with Access to Bantam Lake
9.6 out of 10, Exceptional, (17)
"The lake and all the homes were beautiful and the house was very clean, organized, and felt like home. "
Cozy 2-bedroom Cottage with Access to Bantam Lake
Putnam Valley Vacation Rental: Patio & Lake Views!
Terrace/patio
Putnam Valley Vacation Rental: Patio & Lake Views!
3.0 star property
Putnam Valley Vacation Rental: Patio & Lake Views!
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
View from property
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
10.0 out of 10, Exceptional, (1)
"Great relaxing stay quite and comfortable "
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Candlewood Lake Retreat with year round views
Exterior
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (10)
"Liked outdoor area and fire place "
Candlewood Lake Retreat with year round views
Charming Private and Serene cottage close to I-84 and shopping
Exterior
Charming Private and Serene cottage close to I-84 and shopping
Charming Private and Serene cottage close to I-84 and shopping
Cottage Getaway DogFriendly, Grill, Walk to Lake
Enjoy the morning sunlight streaming through the windows while staying cozy inside. Pull down filter shades on all windows for privacy. (Use of fireplace is not allowed unfortunately!)
Cottage Getaway DogFriendly, Grill, Walk to Lake
10.0 out of 10, Exceptional, (14)
"My husband and I were very happy with our stay here. Sara was a communicative and flexible host, even before we arrived. The place matched our expectations from the listing. The cottage was clean, comfortable and had everything we needed for our multiple day stay. "
The price is SAR 660
SAR 1,530 total
includes taxes & fees
25 Sep - 26 Sep
Cottage Getaway DogFriendly, Grill, Walk to Lake
Dainty New Preston Cottage w/ Dock & Lake Views!
Preston Vacation Rental | 3BR | 2BA | 1,300 Sq Ft | Stairs Required
Dainty New Preston Cottage w/ Dock & Lake Views!
9.0 out of 10, Wonderful, (33)
"We were in need of a nice, relaxing vacation and that’s exactly what we got. There were four of us (me, my husband, my 16-year-old, and my 11-year-old) and we each had our own space. We loved going down to the dock, and there is also a town beach just down the road. The home is filled with fun antiques and reminds you of a clean, well-kept, and charming grandmother’s house. We wanted a low-key vacation, and so we enjoyed short jaunts (less than 15 mins away) to Kent to enjoy its downtown and...
Dainty New Preston Cottage w/ Dock & Lake Views!
Be in Nature at this Gorgeous Riverfront Cabin
Wappinger Cottage on a Summer Evening
Be in Nature at this Gorgeous Riverfront Cabin
10.0 out of 10, Exceptional, (9)
"Stayed here for two nights when we dropped our kid off at college. Lovely, clean and comfortable. Lots of greenery, and the flowing river relaxed us all as we re-packed and prepared for move-in day! Host was very prompt and helpful. Highly recommend."
Be in Nature at this Gorgeous Riverfront Cabin
Lakefront Brewster Vacation Rental w/ Private Dock
Brewster Vacation Rental | 3BR | 2BA | Stairs Required | 2,600 Sq Ft
Lakefront Brewster Vacation Rental w/ Private Dock
10.0 out of 10, Exceptional, (3)
"Family trip consisting of 2 grandparents, 2 parents, and 1 adult grandchild went off without a hitch. The property is so beautiful- meticulously clean house, soft beds and luxury bedding, top notch kitchen appliances, with the most peaceful view of the lake. Excellent communication from host, including helpful welcome book. Fresh loaf of cranberry bread from local farmer’s market was a nice touch. DeCicco’s Market was our go-to for groceries / wish we had one of those at home. Enjoyed...
Lakefront Brewster Vacation Rental w/ Private Dock
Dreamy Hudson Valley Cottage w/ State Park Views
Living area
Dreamy Hudson Valley Cottage w/ State Park Views
3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
Lakefront/nature retreat, 50 miles from NYC, close to Le Chateau (South Salem
Exterior
Lakefront/nature retreat, 50 miles from NYC, close to Le Chateau (South Salem
9.0 out of 10, Wonderful, (8)
"Property was exactly as advertised & in a beautiful location. Laurence was a very attentive but unobtrusive host. Recommended."
Lakefront/nature retreat, 50 miles from NYC, close to Le Chateau (South Salem
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Private Dock
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
10.0 out of 10, Exceptional, (4)
"Loved staying at this spot when dropping our daughter off for school!"
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
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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 SAR 1,873
SAR 3,437 total
includes taxes & fees
23 Sep - 24 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.

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