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Holiday Rentals in Pawling

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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
On the beach, sun-loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (58)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
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."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
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Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (35)
"This sweet little apartment was perfect for my solo stay. Comfortable, quiet, and very easy to get to. Lovely view from the deck. It had a feeling of security and privacy. Vicky was quick with answering my emails."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"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 Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (74)
"Thoroughly enjoyed our stay at Squantz Cottage. Property was well maintained, clean, and convenient. Parking at the cottage can be a little tricky backing out and getting on to the road. An option to park at the main house could be helpful. I would definitely rent again!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (11)
"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 €155
per night
28 May - 29 May
Cabin in the heart of the Hudson Valley, Cabin 4
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (16)
"We really enjoyed staying at this cottage, much better than 2 rooms in a hotel. Very quiet, fully equipped kitchen.Easy to prepare meals when we wished. We visit the Ridgefield area several times per year and will definitely consider staying here again."
Serenity Awaits at this Cozy Lakeside Bungalow
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, (28)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Games room
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, (11)
"Cute."
The price is €202
per night
30 May - 31 May
Peaceful apartment on 3.5 acres w/ artist studio.
Property grounds
Lake Luxury
10.0 out of 10, Exceptional, (8)
"We loved our stay at this home. Plenty of space so we didn’t feel like we were on top of each other, gorgeous kitchen (plus a separate butler’s kitchen!), and lux bathrooms made this rental exactly what we needed. Thanks Gianna!"
Lake Luxury
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (17)
"The property is lovely and well prepared for guests. The location is wonderful. One of our highlights was watching a bald eagle soar over the lake."
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Exterior
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is €155
per night
27 May - 28 May
Cabin in the heart of the Hudson Valley, Cabin 2
Property grounds
Lakefront New York Abode w/ Deck, Grill & Fire Pit
10.0 out of 10, Exceptional, (3)
"Clean, spacious, and many activities in a nice quiet town. The house comfortably fit our 10 people."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Dining
@iHeartNYState 4BR. Hot Tub Jacuzzi Fireplace
7.0 out of 10, Good, (4)
"Oven and stove top very dirty , SPA pool water not clean,no washer and dryer"
The price is €557
per night
28 May - 29 May
@iHeartNYState 4BR. Hot Tub Jacuzzi Fireplace
Property grounds
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, (16)
"What a beautiful home with a spectacular view. We had the most relaxing, fun filled vacation!! The amenities were over and beyond what any of us ever expected."
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (74)
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (7)
"Absolutely loved my stay. The host was incredibly accommodating and went above and beyond to make sure we had everything we needed. The space was stylish, clean, and cozy, with thoughtful touches throughout. The location was perfect, close to all the attractions yet tucked away in a quiet neighborhood. Would highly recommend to anyone looking for a comfortable and enjoyable stay!"
The price is €402
per night
30 May - 31 May
Cozy & Chic Cabin by the Lake, with access to private Beach!
Property grounds
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
10.0 out of 10, Exceptional, (6)
"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.
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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

Deluxe Double Room, 1 Bedroom
Station Inn Pawling
3.0 star property
9.2 out of 10, Wonderful, (141)
"Excellent place to stay after a show at Daryls place! Highly recommend!"
The price is €237
per night
5 Jun - 6 Jun
Station Inn Pawling
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, (1001)
"Easy and safe area . Major highway nearby."
The price is €146
per night
3 Jun - 4 Jun
HYATT house Fishkill/Poughkeepsie
Exterior Standard Room, 2 Double Beds, Non Smoking, Annex Building
Quality Inn Poughkeepsie
2.5 star property
8.0 out of 10, Very good, (232)
"N/A"
The price is €111
per night
28 May - 29 May
Quality Inn 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.

Everything you need to know about Pawling holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pawling holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pawling holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pawling holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pawling. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pawling holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pawling holiday rentals we have selected for you start as low as €155 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pawling rentals

At Expedia, we put the best Pawling holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pawling rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pawling holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pawling. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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
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