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Pawling Vacation Rentals

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Vacation Rentals in Pawling

Stunning Pawling Retreat w/ Ponds & Waterfall
Fridge, microwave, stovetop, dishwasher
Stunning Pawling Retreat w/ Ponds & Waterfall
10.0 out of 10, Exceptional, 2 reviews
"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
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, 76 reviews
"Perfect weather for a getaway! Great location to get to get around. Cottage was perfect for us. Fire pit was great to hang out at. Went kayaking across the street. Beautiful lake. However, the access to the lake was a wee bit steep but we are in shape to handle it. All in all it was a great time!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, 39 reviews
"This is a nice apartment built onto a home in a nice neighborhood cul-de-sac. Beautiful views, quiet, clean. Responsive owners. The shower is small so might not be suitable for all. Enjoyed our week."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Cozy Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
Property grounds
Cozy Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
9.6 out of 10, Exceptional, 35 reviews
"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 Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, 30 reviews
"Very charming one room apartment with bathroom and kitchen area. Beautiful surrounding you with very pleasant hosts"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
On the beach, sun loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, 59 reviews
"We had a lovely weekend stay for a quick family get-away. The main kitchen and living area has spectacular views onto the lake as does the deck where we spent most of our time. The lake is just across the very quiet street. The kitchen is incredibly well stocked, the host super responsive and the rooms very comfortable. We did not use the well equipped basement work-out and additional TV space but it looked great. Easy to get to grocery store, hikes, local attractions but honestly we just loved...
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 38 reviews
"My husband and I greatly enjoyed our stay! We mentioned that we were traveling for our honeymoon and upon our arrival, the host had left a bottle of wine and some little decorations on the dining room table to celebrate our marriage! It was so thoughtful and sweet!! The Vrbo itself was cozy and tidy. We enjoyed cooking in the kitchen and listening to the music of Motown on the cd player. Our host was prompt to respond to messages and answered all questions clearly. We loved staying close to so...
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, 63 reviews
"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.
Spectacular Log Home Estate North Wing Apt
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, 25 reviews
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Property grounds
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, 171 reviews
"This is a perfect house and location on a small beautiful lake in NY. We had a wonderful, relaxing time. Jason is the perfect host!! Very quick to respond. We would love to return sometime."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Serenity Awaits at this Cozy Lakeside Bungalow
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, 18 reviews
"Stayed while attending a local wedding and wished we had had more time to hang out at the house! The lake is beautiful and the house had everything we needed! Hope to come back some day!"
Serenity Awaits at this Cozy Lakeside Bungalow
Spacious restored Victorian w/ wraparound porch
Fridge, microwave, oven, stovetop
Spacious restored Victorian w/ wraparound porch
9.4 out of 10, Exceptional, 10 reviews
"The property was gorgeous, the house large enough to accommodate our group. The kitchen was well stocked. We used the pool, hot tub, fire pit, and pool table. The indoor and outdoor speakers were a nice touch. I would definitely recommend this home I had to reach out to our host 2 days before check in to find out how to get in- usually that is communicated earlier than that. I had informed the host that we were going to have a luncheon for 10 additional people after the memorial service and was...
Spacious restored Victorian w/ wraparound porch
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
9.8 out of 10, Exceptional, 19 reviews
"Our family enjoyed our stay at the Cottage during our recent visit to CT for our son's college graduation. The views of the lake from the living room, the deck and the patio with fire pit are great and very peaceful. The kitchen was nicely outfitted with everything needed to cook and prepare meals. The only drawback was that there were no closets or chest of drawers in the (2) basement bedrooms. There was no place to unpack and hang our clothes for the 4 days we were there; the only closet was...
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, 74 reviews
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
Property grounds
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
10.0 out of 10, Exceptional, 6 reviews
"Great property, very clean and host was quick to reply. We were impressed with the amenities available (most places don’t have detergent, etc) and the view was amazing! We didn’t have time to go to the dock but it looked very nice! Wish we had time to stay longer. We will definitely try to stay there again for our next family event"
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, 8 reviews
"We’d go back."
The price is ￥39,465
￥77,194 total
includes taxes & fees
Jul 1 - Jul 2
Cozy & Chic Cabin by the Lake, with access to private Beach!
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very Good, 11 reviews
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is ￥17,190
￥25,755 total
includes taxes & fees
Jun 24 - Jun 25
Cabin in the heart of the Hudson Valley, Cabin 4
Cozy country efficiency in the Hudson Valley
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, 42 reviews
"We spent a wonderful night at this apartment. The space is so comfortable and peaceful. It is next to the owners' home but very private and extremely quiet. The neighborhood is a dead end and has few cars. The apartment feels sizable and is well laid out. It was clean and well stocked. The owners were very responsive when we had a question. We would absolutely come back!"
The price is ￥23,679
￥34,256 total
includes taxes & fees
Jul 8 - Jul 9
Cozy country efficiency in the Hudson Valley
Cabin in the heart of the Hudson Valley, Cabin 2
Exterior
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, 3 reviews
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is ￥17,190
￥25,755 total
includes taxes & fees
Jun 24 - Jun 25
Cabin in the heart of the Hudson Valley, Cabin 2
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, 22 reviews
"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
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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

Station Inn Pawling
Deluxe Double Room, 1 Bedroom | Free WiFi, bed sheets
Station Inn Pawling
3.0 star property
9.2 out of 10, Wonderful, 146 reviews
"Lot of charm at the Sation Inn! And it located within very short walking distance to shops/restaruants/bar.. Great spot"
The price is ￥36,191
￥40,580 total
includes taxes & fees
Jul 2 - Jul 3
Station Inn Pawling
Ethan Allen Hotel
Seasonal outdoor pool
Ethan Allen Hotel
3.5 star property
7.8 out of 10, Good, 1,002 reviews
"Haven't been to Ethan Allen in years. I was in town on business. Still as I remember it. Great stay..!"
The price is ￥17,624
￥20,268 total
includes taxes & fees
Jun 25 - Jun 26
Ethan Allen Hotel
HYATT house Fishkill/Poughkeepsie
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, 1,000 reviews
"They have a little bit of everything, including an indoor heated pool, a hot tub, laundry, a fitness center, and a full breakfast as opposed to those with a continental breakfast. The staff is very friendly, and the rooms as very comfortable."
The price is ￥22,568
￥25,306 total
includes taxes & fees
Jul 2 - Jul 3
HYATT house Fishkill/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.

Search for holiday rentals in Pawling on Expedia! You can easily find your home rentals, villas, holiday apartments in Pawling using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Pawling?

Yes, we offer vacation rentals near well known points of interest in Pawling, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Pawling?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This vacation home rental near Pawling is located on a lake and has a fireplace, a patio, and a barbecue grill 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 a spa tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Pawling?

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

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 vacation rentals like in Pawling?

Vacation rentals are private accommodations you can stay in for several days or more in Pawling. Vacation rentals offer extras such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips or small group gatherings.

Recent reviews of Pawling properties
Expedia verified reviews

Holiday Inn Poughkeepsie, an IHG Hotel

Holiday Inn Poughkeepsie, an IHG Hotel

5/5 Excellent
"Staff is friendly"
A verified traveler stayed at Holiday Inn Poughkeepsie, an IHG Hotel
Posted 1 day ago
Holiday Inn Poughkeepsie, an IHG Hotel