Title: Pawling Vacation Rentals from CA $175: 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)

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6278767&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6278767&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=6278767&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=6278767&startDate=2026-07-24&endDate=2026-07-26&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

![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/95000000/94960000/94953800/94953757/15697af2.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)

### 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 $298

CA $719 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)

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=2026-04-15&endDate=2026-04-16&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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CHALET)

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## Top Pawling Hotel Reviews

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

### Ethan Allen Hotel

8/10 Good

"Breakfast was fresh, and the hotel was very well Kept."

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

![HYATT house Fishkill/Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/w3836h2558x4y3-858cbdd6_y.jpg)

### HYATT house Fishkill/Poughkeepsie

10/10 Excellent

"My family and I had a 360° experience here the welcoming was genuine. The room was comfortable the amenities the cleanliness and the hospitality, hands down, generous. Filled with gratitude, wonderful experience. "

[](https://expedia.ca/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.Hotel-Information)

![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

"Staff is always easy, check in is quick and easy, right off the highway. Always my fav place to stay "

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

"Very clean. Nice room. Noce property "

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

![SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/11ffbd82_y.jpg)

### SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent

"Breakfast was great, and also I would like to give an 100% to Ryan the night auditor, great service beyond. He represent what is a service about. Awesome n Outstanding "

[](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.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

10/10 Excellent

"Super friendly staff. Beautiful, clean rooms. Great indoor pool and gym."

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

![Heritage Hotel, Golf & Conference Center](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/beb7cb97_y.jpg)

### Heritage Hotel, Golf & Conference Center

6/10 Okay

"The room was very clean and comfortable. The staff is really great! Our room must have had a lose pipe or vent in the wall behind the shower so it would bang on the wall alot. Once we got used to it it wasnt bad. That is my only complaint. The stay other then that was great!"

[](https://expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information)

![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/1ee75d40_y.jpg)

### Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"Hotel gym was fantastic, storyteller restaurant food & drinks amazing. One of the best complimentary breakfasts we’ve ever had. Plan on returning. 5 stars all the way!"

[](https://expedia.ca/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information)

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

### Spark by Hilton Fishkill

10/10 Excellent

"The breakfast menu can improve when people stay more than one night. Room space is good."

[](https://expedia.ca/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.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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## Frequently asked questions

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