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Search Holiday Rentals in Pawling

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Top Holiday Rentals in Pawling

Fridge, microwave, stovetop, dishwasher
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
Smart TV, fireplace, ping pong, stereo
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
10.0 out of 10, Exceptional, (9)
"The house had everything we needed and was the perfect winter getaway for our group to celebrate a birthday! Would rent again and again! Amazing property manager who was communicative and gave us all the information we needed. Amazing amenities better than a hotel stay! They have thought of everything - stocked with games and everything you should need for a great vacation! Comfortable and fabulous!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Property grounds
Hudson River View Suite-romantic getaway with fireplace/private deck-75 min NYC
10.0 out of 10, Exceptional, (33)
"Very nice property, immaculately clean and very close to the Riverside Art Venue. Both quiet and convenient for my time in Newburgh. I would definitely stay here again."
The price is £144
includes taxes & fees
19 May - 20 May
Hudson River View Suite-romantic getaway with fireplace/private deck-75 min NYC
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View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (15)
"We so enjoyed our stay! The house was perfect for our family, conveniently located close to extended family and with the most beautiful view. The house had everything we needed and provided the perfect home base for spring break in our hometown. We even got to experience an earth quake ;) thank you!!"
Serenity Awaits at this Cozy Lakeside Bungalow
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (61)
"The property and house were beautiful, out of the way but beautiful. The fire pit, sunroom, and porch were amazing. It was great for decompressing after a West Point graduation. Thank you for sharing your little piece of heaven."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (24)
"The place was amazing! It was a very beautiful place and was close to everything I was needing to do. It was extremely clean and cozy and I would stay again for sure!"
Spectacular Log Home Estate North Wing Apt
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (6)
"Marianna was super responsive and the house was adorable!"
The price is £373
includes taxes & fees
2 Jun - 3 Jun
Cozy & Chic Cabin by the Lake, with access to private Beach!
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (16)
"This house is located minutes from the highway making it easy to get to. Its a very scenic and country area so you feel farther away then you are. The house is extremely clean and well appointed it sits up high on a hill so you can enjoy the veiw of the country house across the street which has a small creek and gardens to enjoy theres even a pool to enjoy in summer months and a fire pit .this house was peaceful and perfect for the quick weekend getaway that we all needed. The host Pat was...
The price is £209
includes taxes & fees
6 May - 7 May
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (1)
"We went to the area to celebrate my husbands 30th birthday with some friends and absolutely loved the home. It was brand new and decorated immaculately. It comfortably fit our group and we thoroughly enjoyed our time there. The hosts were super accommodating and quick to respond. Would absolutely reccomend and go again!"
The price is £739
includes taxes & fees
5 May - 6 May
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Property grounds
NEW 2BR 2B Direct Waterfront Candlewood Lake Home~ Views & Dock~ WINTER SPECIAL!
10.0 out of 10, Exceptional, (14)
"This property was absolutely beautiful, and the property manager Lisa was kind and made herself available if needed. Absolutely plan to come back again."
NEW 2BR 2B Direct Waterfront Candlewood Lake Home~ Views & Dock~ WINTER SPECIAL!
Smart TV, fireplace
The Long View of Candlewood Lake
10.0 out of 10, Exceptional, (5)
"Patricia is an outstanding host with great communication and always pleasantly and quickly responding! The house is just beautiful - clean, comfortable and has clear 'welcome guide'. The location is amazing. We had a great, relaxing time and appreciate it so very much. Everything was perfect! Really want to book again! Thank you!"
The Long View of Candlewood Lake
Property grounds
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, (168)
"If you need a relaxing few days in the winter, very good place. Great views and quiet is the key."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (15)
"From the moment we came we felt right at home! Such a comfortable place to stay! Every morning we were greeted by a beautiful bald eagle on the lake as well as the chitter chatter of birds. For those who have a hard time climbing stairs, this is NOT the place for you. Bedrooms as well as bathrooms are not on the main level. No matter we would definitely want to stay again!"
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Property grounds
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (6)
"This house was exactly as advertised and very charming. The owners were very easy to work with. We had a beautiful view of the lake from the porch. We would stay here again."
Candlewood Lake Retreat with year round views
Exterior
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
10.0 out of 10, Exceptional, (71)
"Great place to celebrate a 40th birthday. Place was clean and comfortable. Great view. Hot tub, lawn games, movie theater, pool table, and more were all great."
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
1 bedroom, desk, iron/ironing board, travel cot
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."
The price is £212
includes taxes & fees
6 May - 7 May
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (37)
"This property is beautiful!! Spotless, functional and private. We absolutely loved the experience and will DEFINITELY be back again."
Cozy country efficiency in the Hudson Valley
Games room
Peaceful apartment on 3.5 acres w/ artist studio.
9.8 out of 10, Exceptional, (10)
"The place was cozy quiet and clean. Exactly what I was looking for."
The price is £173
includes taxes & fees
6 May - 7 May
Peaceful apartment on 3.5 acres w/ artist studio.
Fridge, microwave, oven, stovetop
Spacious restored Victorian w/ wraparound porch
9.8 out of 10, Exceptional, (7)
"We had a very pleasant stay for a momentous occasion where my wife's family and my family met for the first time. The kitchen will always be the gathering spot as both our cultures enjoy food and this kitchen proved to be an excellent space. The billiards room was also a great hang out room and the porch areas were perfect for photo taking."
Spacious restored Victorian w/ wraparound porch
Property grounds
Cozy Rustic Getaway w/ HBO, Porch & Grill Near Lake
9.8 out of 10, Exceptional, (10)
"This property is a serene location in the Hudson Highlands that has convenience and good proximity to stores & multiple communities in the area. This home had everything we were looking for and was very comfortable for us. Our host was great too!"
Cozy Rustic Getaway w/ HBO, Porch & Grill Near Lake
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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.

Other types of properties in Pawling you may be interested in

Exterior
Hyatt Place Poughkeepsie / Hudson Valley
3.0 star property
8.8 out of 10, Excellent, (1000)
"Great Property! The room was fantastic and shower had abundant water pressure. Breakfast was 10/10, bacon, hash, real eggs and hashbrowns. One of the better properties we have stayed at in three years of over the road work."
The price is £92
includes taxes & fees
20 May - 21 May
Hyatt Place Poughkeepsie / Hudson Valley
Exterior
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, (1002)
"Pool area is extremely slippery. Pillows weren’t good. Everything else was great"
The price is £120
includes taxes & fees
5 May - 6 May
HYATT house Fishkill/Poughkeepsie
Bar (on property)
DoubleTree by Hilton Poughkeepsie
4.0 star property
8.2 out of 10, Very good, (957)
"Great stay. Hotel staff was friendly. Rooms were clean and hotel is just steps away from the concert hall venue. Easy free parking. "
The price is £110
includes taxes & fees
28 May - 29 May
DoubleTree by Hilton Poughkeepsie
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.

Frequently asked questions

Are there holiday rentals in Pawling?

Yes, there are holiday rentals close to the most popular sights in Pawling, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pawling has to offer?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of Pawling is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Pawling?

Choose from 4 Expedia holiday rentals in Pawling for a memorable holiday.

What can I see and do in Pawling?

While exploring the area, visit family-friendly sights like SplashDown Beach, or get outside and enjoy nature at Squantz Pond State Park. Other places in town to visit include John Kane House and Akin Free Library.

What are holiday rentals like in Pawling?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pawling. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.

Recent reviews of Pawling properties
Expedia verified reviews

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

5/5 Excellent
"It could use some updating!"
A verified traveller stayed at Quality Inn & Suites Fishkill South near I-84
Posted 17 hours ago
Quality Inn & Suites Fishkill South near I-84