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Pawling Holiday Rentals

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Check prices for these dates

Tonight
13 Nov - 14 Nov
Tomorrow
14 Nov - 15 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Holiday Rentals in Pawling

Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fishkill
9.6 out of 10, Exceptional, (45)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
The price is HK$2,013
HK$2,593 total
includes taxes & fees
30 Nov - 1 Dec
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2

Newburgh
9.4 out of 10, Exceptional, (27)
"My partner and I stayed at the cabin for a writing retreat/getaway. It served us well and was perfect for our short trip. The host, Julie was very kind and helpful throughout our stay!"
United States
Thani B.
The price is HK$847
HK$1,368 total
includes taxes & fees
17 Nov - 18 Nov
Cabin in the heart of the Hudson Valley, Cabin 2
Interior
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is HK$3,357
HK$5,370 total
includes taxes & fees
14 Nov - 15 Nov
Large,Cozy,Bright Apartment, Business Themed.
Dining
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

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
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,351
HK$3,513 total
includes taxes & fees
17 Nov - 18 Nov
Rustic Cabin in Fishkill!
Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (16)
"Excellent stay !!!! Everything was perfect. Communication was phenomenal.!!!!"
United States
daniellle
The price is HK$699
HK$960 total
includes taxes & fees
23 Nov - 24 Nov
New One Bedroom Apartment Centrally Located in Southbury
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Carmel Hamlet
10.0 out of 10, Exceptional, (94)
"We loved our stay. It was great for a family Thanksgiving"
United States
Edmund F.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Dining
Peaceful Vintage Home with Private Lake in Redding, CT.

Peaceful Vintage Home with Private Lake in Redding, CT.

2.0 star property
Redding
10.0 out of 10, Exceptional, (2)
"Property was beautiful in a very quiet and peaceful area. Our host Kadriia was so amazing and would respond so quickly to any questions we had and communicated clearly. My wife and our friends had a Halloween themed wedding party for our friends who couldn’t make it to the actual wedding and we couldn’t have had a better time. "
United States
Connor K.
The price is HK$2,798
HK$4,562 total
includes taxes & fees
16 Nov - 17 Nov
Peaceful Vintage Home with Private Lake in Redding, CT.
Property grounds
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury
10.0 out of 10, Exceptional, (24)
"Beautiful house with amazing views. Can’t wait to stay again. Great location too! Close to everything (shopping/food/activities) but located on a very quiet dead end. Owners were easy to communicate with and very friendly. "
United States
Mary M.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Interior
Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

Waccabuc
4.0 out of 10, (2)
"Clean but minimalist, big empty basement, good for a cheap stay near Caramoor"
United States
Patrick M.
The price is HK$1,144
HK$1,586 total
includes taxes & fees
16 Nov - 17 Nov
Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie
10.0 out of 10, Exceptional, (2)
"House worked perfectly for our needs. Newly renovated home. Parking was plentiful behind the home. "
United States
Wayne S.
The price is HK$1,287
HK$4,520 total
includes taxes & fees
16 Nov - 17 Nov
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Children’s area
Hickory on Willow Lake

Hickory on Willow Lake

Fishkill
9.6 out of 10, Exceptional, (4)
"We stayed one night. Would loved to have stayed longer. Beautiful property. "
United States
Christine B.
The price is HK$4,060
HK$5,716 total
includes taxes & fees
2 Dec - 3 Dec
Hickory on Willow Lake
Terrace/patio
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Holmes
10.0 out of 10, Exceptional, (196)
"A sweet little cabin on a quiet lake was exactly what I was looking for. My overall experience was absolutely wonderful."
United States
Janine H.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Outdoor dining
Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4

Newburgh
9.2 out of 10, Wonderful, (25)
"Great place to stay for a Beacon/Newburgh trip if you have a car, or like me, don’t mind hilly bike ride to and from. Cozy and affordable. "
United States
Derek L.
The price is HK$847
HK$1,368 total
includes taxes & fees
16 Nov - 17 Nov
Cabin in the heart of the Hudson Valley, Cabin 4
Property grounds
Wappinger Cottage - Scandinavian retreat on a creek

Wappinger Cottage - Scandinavian retreat on a creek

Poughkeepsie
10.0 out of 10, Exceptional, (23)
"We had a wonderful stay. The Cabin is ideally situated in a very tranquil spot. Perfectly appointed, we couldn't have been happier with our stay."
United States
Phoebe J.
Wappinger Cottage - Scandinavian retreat on a creek
Smart TV, fireplace, books
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

New Fairfield
10.0 out of 10, Exceptional, (14)
"Was a great find. Updated, spacious and clean."
United States
Paul B.
The price is HK$1,519
HK$3,954 total
includes taxes & fees
16 Nov - 17 Nov
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC

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 HK$1,049
HK$2,164 total
includes taxes & fees
19 Nov - 20 Nov
Charming 1-bedroom apartment in Carmel with WiFi, AC
Outdoor dining
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

New Fairfield
9.8 out of 10, Exceptional, (35)
"We stayed for 3 weeks it was lovely!"
United States
Sarah T.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Outdoor pool
Private lake escape

Private lake escape

Putnam Valley
Private lake escape
Living area
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

2.0 star property
Poughkeepsie
8.6 out of 10, Excellent, (10)
"The owner was very friendly and helpful. The building was beautiful and the apartment perfect for our needs. Lovely historic home that's been modernized without losing its vintage charm. Would definitely stay here again."
United States
Kierin
The price is HK$1,504
HK$1,762 total
includes taxes & fees
16 Nov - 17 Nov
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
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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Top Pawling Hotel Reviews

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Clean"
manuel 1-night trip
Posted 2 days ago
Quality Inn & Suites Fishkill South near I-84

Find out more about Pawling

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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 Akin Free Library and Pawling 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.