Holiday Rentals in Pawling

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Pawling

Holiday Home in Fishkill

9.6 out of 10, Exceptional, (47)
"Great place for a quiet stay"
United States
Shawn M.
The price is €295
includes taxes & fees
30 Nov - 1 Dec
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Holiday Home in Brookfield

9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Holiday Home in Newburgh

9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is €605
includes taxes & fees
30 Nov - 1 Dec
Large,Cozy,Bright Apartment, Business Themed.

Holiday Home in New Fairfield

9.2 out of 10, Wonderful, (34)
"Amazing beautiful place!! Everything clean!! Definitely going to come back! "
United States
Andrew E.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Cabin in Fishkill

10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is €399
includes taxes & fees
1 Dec - 2 Dec
Rustic Cabin in Fishkill!

Holiday Home in Redding

2.0 star property
10.0 out of 10, Exceptional, (2)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
The price is €670
includes taxes & fees
14 Dec - 15 Dec
Peaceful Vintage Home with Private Pond in Redding, CT.

Cabin in Newburgh

9.4 out of 10, Exceptional, (29)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
The price is €177
includes taxes & fees
30 Nov - 1 Dec
Cabin in the heart of the Hudson Valley, Cabin 2

Holiday Home in Fishkill

9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
The price is €493
includes taxes & fees
30 Dec - 31 Dec
Hickory on Willow Lake

Holiday Home in Highland

10.0 out of 10, Exceptional, (18)
"Very nice location and private."
United States
Patrick P.
The House In Highland- Secluded Retreat

Holiday Home in Poughkeepsie

10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
The price is €509
includes taxes & fees
7 Dec - 8 Dec
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Cabin in Carmel

3.0 star property
10.0 out of 10, Exceptional, (3)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Holiday Home in Danbury

10.0 out of 10, Exceptional, (24)
"Gorgeous views and comfortable stay!"
United States
Sam C.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Holiday Home in Fishkill

9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is €627
includes taxes & fees
30 Dec - 31 Dec
Chestnut on Willow Lake

Cottage in Poughkeepsie

10.0 out of 10, Exceptional, (23)
"This was the perfect get away spot! Serene location, lovely amenities, and a gracious host."
United States
Laurie C.
Wappinger Cottage - Scandinavian retreat on a creek

Cabin in Holmes

10.0 out of 10, Exceptional, (196)
"Great place to get away. Absolutely recommend it. "
United States
Demian B.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Holiday Home in New Fairfield

10.0 out of 10, Exceptional, (80)
"Beautiful fun home, great owner!"
United States
Robin B.
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Apartment in Beacon

9.4 out of 10, Exceptional, (10)
"The views from the property match the pictures and in a great accessible location "
United States
Isis J.
Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA

Apartment in Newburgh

9.8 out of 10, Exceptional, (65)
"Such a cute place to stay"
United States
Melissa
The price is €290
includes taxes & fees
18 Dec - 19 Dec
Cozy country efficiency in the Hudson Valley

Holiday Home in Fishkill

The price is €647
includes taxes & fees
8 Dec - 9 Dec
Red Cottage - Lakeside Property!

Apartment in Carmel Hamlet

9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is €245
includes taxes & fees
2 Dec - 3 Dec
Charming 1-bedroom apartment in Carmel with WiFi, AC
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pawling Hotel Reviews

Find out more about Pawling

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 €177 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Pawling offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and a coffee maker, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Pawling?

Cultural attractions include John Kane House, whereas Edward R Murrow Park is a spot to enjoy nature. Other places in town to visit include Pawling Free Library and Pawling Village Hall.

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.