Title: Pawling Vacation Rentals from CA $171: Short-Term Rentals for 2026 | Expedia.ca

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![Appalachian Trail](https://images.trvl-media.com/place/6278767/77ffe529-3d3e-49fe-8ae7-6cb44a357bf5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6278767/77ffe529-3d3e-49fe-8ae7-6cb44a357bf5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6278767&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6278767&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6278767&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=6278767&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pawling vacation rentals

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90900000/90899400/90899359/7ce45210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90899400/90899359/22854ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90900000/90899400/90899359/w1024h677x0y3-55eed7d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90900000/90899400/90899359/w1024h680x0y3-a5c935c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in the heart of the Hudson Valley, Cabin 3

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899359.Hotel-Information)

Newburgh

9.8/10

Exceptional

(14 reviews)

"We had a great stay, everything you need is provided. Would recommend to anyone."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bill W.

CA $232

CA $386 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899359.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/116000000/115850000/115840700/115840689/b1664c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/116000000/115850000/115840700/115840689/f7fbdc08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115850000/115840700/115840689/85846b72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115850000/115840700/115840689/90232191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

[](https://www.expedia.ca/Millbrook-Hotels-Charming-3-Bedroom-Apartment-With-WiFi-And-AC-In-Fabulous-Millbrook-NY.h115840689.Hotel-Information)

Millbrook

10/10

Exceptional

(2 reviews)

"Tanya goes above and beyond for her guests. Thanks so much for the stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lindsay S.

CA $439

CA $680 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Millbrook-Hotels-Charming-3-Bedroom-Apartment-With-WiFi-And-AC-In-Fabulous-Millbrook-NY.h115840689.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h681x0y2-21ff539b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/c421cfb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h680x0y3-8188dd85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h680x0y3-d877abc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in the Heart of the Hudson Valley, Cabin 1

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90897766.Hotel-Information)

Newburgh

10/10

Exceptional

(32 reviews)

"Great overnight spot, especially with a dog."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ed C.

CA $232

CA $386 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90897766.Hotel-Information)

![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/fe9d9847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/c22e2a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/d25ce94c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/e40d957c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dainty New Preston Cottage w/ Dock & Lake Views!

[](https://www.expedia.ca/New-Preston-Hotels-Dainty-New-Preston-Cottage-W-Dock-Lake-Views.h94953757.Hotel-Information)

New Preston

CA $294

CA $709 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/New-Preston-Hotels-Dainty-New-Preston-Cottage-W-Dock-Lake-Views.h94953757.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/38809636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/416c2b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/8bc06f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/cfa82cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike. 

[](https://www.expedia.ca/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information)

Carmel Hamlet

9.8/10

Exceptional

(13 reviews)

"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hannah P.

CA $229

CA $483 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/320bd4a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/2a0deaa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/a4d2d147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/be0aeba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 1-bedroom apartment in Carmel with WiFi, AC

[](https://www.expedia.ca/Carmel-Hotels-Charming-1-Bedroom-Apartment-In-Carmel-With-WiFi.h110784547.Hotel-Information)

Carmel Hamlet

9.0/10

Wonderful

(2 reviews)

"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Emmett

CA $185

CA $381 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/Carmel-Hotels-Charming-1-Bedroom-Apartment-In-Carmel-With-WiFi.h110784547.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/a27e5755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/03710a7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/c225355f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/5e31b747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy country efficiency in the Hudson Valley

[](https://www.expedia.ca/Newburgh-Hotels-Cozy-Country-Efficiency-In-The-Hudson-Valley.h45742802.Hotel-Information)

Newburgh

9.8/10

Exceptional

(68 reviews)

"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lou F.

CA $226

CA $434 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Newburgh-Hotels-Cozy-Country-Efficiency-In-The-Hudson-Valley.h45742802.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112620000/112615000/112614966/a522239b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/113000000/112620000/112615000/112614966/579bd352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112620000/112615000/112614966/8e00476e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112620000/112615000/112614966/98254145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Cabin in Fishkill!

[](https://www.expedia.ca/Fishkill-Hotels-Charming-Cabin-In-Fishkill.h112614966.Hotel-Information)

Fishkill

9.6/10

Exceptional

(4 reviews)

"What a sweet little spot in a gorgeous area - clean, simple, and beautiful. Thanks for a great stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julia T.

CA $445

CA $636 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Fishkill-Hotels-Charming-Cabin-In-Fishkill.h112614966.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/79000000/78470000/78462800/78462782/8d5d22b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78470000/78462800/78462782/1703db8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78470000/78462800/78462782/6e2aacca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78470000/78462800/78462782/096e4191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

[](https://www.expedia.ca/New-Fairfield-Hotels-Farmhouse-Apartment-On-Beautiful-Grounds-2-Mi-To-Candlewood-Lake.h78462782.Hotel-Information)

New Fairfield

10/10

Exceptional

(35 reviews)

"Stunning property!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Samantha

CA $377

CA $659 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/New-Fairfield-Hotels-Farmhouse-Apartment-On-Beautiful-Grounds-2-Mi-To-Candlewood-Lake.h78462782.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/115000000/114730000/114722300/114722240/4752702b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114730000/114722300/114722240/0014b4a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114730000/114722300/114722240/e6d64eca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/115000000/114730000/114722300/114722240/672c1a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mid Century Modern Studio w/ Full Kitchen - Newly Built

[](https://www.expedia.ca/Kent-Hotels-Mid-Century-Modern-Studio-W-Full-Kitchen-Newly-Built.h114722240.Hotel-Information)

Kent

10/10

Exceptional

(11 reviews)

"We had a great stay, very cute town and close to our destination "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Danielle F.

CA $240

CA $308 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Kent-Hotels-Mid-Century-Modern-Studio-W-Full-Kitchen-Newly-Built.h114722240.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/07823851.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/fb67eeb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/c873cf3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/a51d4c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy One Bedroom Apartment Centrally Located in Southbury

[](https://www.expedia.ca/Southbury-Hotels-Simple-Living-Retreat-1-Bedroom-Apartment.h111828646.Hotel-Information)

Southbury

10/10

Exceptional

(23 reviews)

"Perfect sized apartment for a short stay - very convenient to my destination"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

S

CA $125

CA $171 total

includes taxes & fees

Apr 4 - Apr 5

[](https://www.expedia.ca/Southbury-Hotels-Simple-Living-Retreat-1-Bedroom-Apartment.h111828646.Hotel-Information)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/5bb48ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/bf2402ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/f4377701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/w1179h786x0y7-46a94465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

[](https://www.expedia.ca/Carmel-Hotels-Beautiful-Escape-Hudson-Valley-LakeHouse-90min-From-NYC-30min-From-Beacon.h102342378.Hotel-Information)

Carmel Hamlet

10/10

Exceptional

(19 reviews)

"Lovely house with all the amenities. We had a wonderful time."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Diana P.

CA $740

CA $1,340 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Carmel-Hotels-Beautiful-Escape-Hudson-Valley-LakeHouse-90min-From-NYC-30min-From-Beacon.h102342378.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112620000/112615100/112615005/dd15c573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/113000000/112620000/112615100/112615005/dec095c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112620000/112615100/112615005/325abde1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112620000/112615100/112615005/003312bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Red Cottage - Lakeside Property!

[](https://www.expedia.ca/Fishkill-Hotels-Red-Cottage-Lakeside-Property.h112615005.Hotel-Information)

Fishkill

CA $717

CA $1,026 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Fishkill-Hotels-Red-Cottage-Lakeside-Property.h112615005.Hotel-Information)

![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/46f74edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/w1436h1440x0y0-175a22f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/16dfe03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/b6c9432d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Awesome Lake Home with tons of fun!

[](https://www.expedia.ca/New-Fairfield-Hotels-Awesome-Lake-Home-With-Tons-Of-Fun.h104373791.Hotel-Information)

New Fairfield

9.8/10

Exceptional

(7 reviews)

"Great spot "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mike P.

CA $556

CA $984 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/New-Fairfield-Hotels-Awesome-Lake-Home-With-Tons-Of-Fun.h104373791.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/13d8fc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/7dc21331_edited_faa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/99922af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/1c766ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

[](https://www.expedia.ca/Putnam-Valley-Hotels-Walk-To-Lake-Cottage-With-Office-For-Quiet-Days-And-Easy-Work.h91391396.Hotel-Information)

Putnam Valley

9.8/10

Exceptional

(23 reviews)

"Great, clean house, nice accommodating host. Would stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Heather T.

CA $229

CA $664 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Putnam-Valley-Hotels-Walk-To-Lake-Cottage-With-Office-For-Quiet-Days-And-Easy-Work.h91391396.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/0da715d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining tables](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/7d1ae479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/377f36e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/ee5fa657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chestnut on Willow Lake

[](https://www.expedia.ca/Fishkill-Hotels-Chestnut-On-Willow-Lake.h112584776.Hotel-Information)

Fishkill

9.6/10

Exceptional

(4 reviews)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Doria W.

CA $679

CA $977 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Fishkill-Hotels-Chestnut-On-Willow-Lake.h112584776.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120670000/120665300/120665201/bbe9c489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120670000/120665300/120665201/78c5ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120670000/120665300/120665201/c4f46f0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120670000/120665300/120665201/5c889ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Perch in the Purchase -- Cozy, unique, and private

[](https://www.expedia.ca/Southbury-Hotels-Entire-Guesthouse-In-Southbury.h120665201.Hotel-Information)

Southbury

10/10

Exceptional

(1 review)

"Beautiful place. Very clean & welcoming "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris

CA $185

CA $300 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Southbury-Hotels-Entire-Guesthouse-In-Southbury.h120665201.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/05c87dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/3933ec39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/4390f269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/67ba7f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/New-Fairfield-Hotels-Private-Beautiful-Home-Family-Friendly-1-Min-Walk-To-Candlewood-Lake.h100167349.Hotel-Information)

New Fairfield

10/10

Exceptional

(18 reviews)

"Great location and condition. Roome enough for everyone."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christopher H.

[](https://www.expedia.ca/New-Fairfield-Hotels-Private-Beautiful-Home-Family-Friendly-1-Min-Walk-To-Candlewood-Lake.h100167349.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/bdac6c18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/fd769a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/4388309b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/d8805194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Country outside the city " 3 bedrooms 2 full bathrooms 

[](https://www.expedia.ca/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information)

Holmes

9.6/10

Exceptional

(4 reviews)

"Great house! We had a fantastic weekend!! Thank you so much "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

pamela w.

CA $341

CA $881 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/69000000/68470000/68467800/68467717/d309f8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/69000000/68470000/68467800/68467717/184fcf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/69000000/68470000/68467800/68467717/2ac6746a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/69000000/68470000/68467800/68467717/a2ec50f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-1-Loft-Main-St-Beacon-Luxury-Steam-Shower-Kitchen.h68467717.Hotel-Information)

Beacon

10/10

Exceptional

(48 reviews)

"Great place!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sara B.

CA $158

CA $340 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-1-Loft-Main-St-Beacon-Luxury-Steam-Shower-Kitchen.h68467717.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08&regionId=6278767&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America&regionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America&regionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America&regionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America&regionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America&regionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VILLA)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America&regionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CHALET)

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## Top Pawling Hotel Reviews

![Best Western Fishkill Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/12500/12443/847efacf_y.jpg)

### Best Western Fishkill Inn & Suites

10/10 Excellent

"The property and staff were amazing. The breakfast was the best breakfast I’ve ever had at a hotel. "

[](https://expedia.ca/Fishkill-Hotels-Best-Western-Fishkill-Inn-Suites.h12443.Hotel-Information)

![Best Western Danbury/Bethel](https://images.trvl-media.com/lodging/1000000/10000/4900/4841/b09513bc_y.jpg)

### Best Western Danbury/Bethel

8/10 Good

"Location "

[](https://expedia.ca/Danbury-Hotels-Best-Western-DanburyBethel.h4841.Hotel-Information)

![Ethan Allen Hotel](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/bb9d6c7e_y.jpg)

### Ethan Allen Hotel

10/10 Excellent

"Very good value. I’d contacted the property via Expedia after my flight was cancelled to let them know I’d be a day late. They said this message didn’t get to them and I had to pay them directly however Expedia were terrific about getting me a quick refund."

[](https://expedia.ca/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information)

![Hyatt Place Poughkeepsie / Hudson Valley](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd_y.jpg)

### Hyatt Place Poughkeepsie / Hudson Valley

8/10 Good

"Good"

[](https://expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information)

![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/ee108dad_y.jpg)

### Hampton Inn & Suites Poughkeepsie

10/10 Excellent

"Clean room with comfortable bed and nice bathroom. Friendly staff."

[](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information)

![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg)

### Courtyard by Marriott Poughkeepsie

10/10 Excellent

"Lakesha was a delightful young lady who checked me in. The stay was great. The only negative was the room next to me was full of unsupervised children who ran screaming down the hallway close to bedtime. But that was not the hotels fault. I love that there is a Starbucks in the lobby. My daughter in law worked in the restaurant during high school decades ago so I was curious to see if it was maintained well. It was a pleasant surprise to find it so clean and modern! It’s a nice place with shopping and restaurants nearby. "

[](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information)

![Hampton Inn Fishkill](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f57ee72e_y.jpg)

### Hampton Inn Fishkill

8/10 Good

"nice breakfast, nice people"

[](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information)

![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg)

### Spark by Hilton Fishkill

8/10 Good

"Overall my experience was good. I was hoping for more scrambled eggs and bacon. There was a homeless guy living in his car that was a bit nerve racking, but otherwise harmless. "

[](https://expedia.ca/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information)

![Home2 Suites By Hilton Poughkeepsie](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/7472348e_y.jpg)

### Home2 Suites By Hilton Poughkeepsie

8/10 Good

"Clean property, friendly staff. Perfect for overnight stay, only negative is breakfast offerings, we travelled with college sports team…only one bagel, told an hour wait for bread to defrost! Could’ve have been better prepped for catering otherwise no issues. "

[](https://expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information)

## Find out more about Pawling

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pawling. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Pawling ](https://expedia.ca/Pawling-Private-Vacation-Homes.d6278767-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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## Frequently asked questions

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

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