Photo by Marina Timo

Search Vacation Homes in Pawling

Start date: Check-in selected.
To Date
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 3 - Oct 5
In one month
Oct 17 - Oct 19
In two months
Nov 14 - Nov 16
In three months
Dec 12 - Dec 14

Vacation Homes in Pawling

Our top choices for Pawling vacation homes

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Outdoor dining

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Charming 1870 cape cottage in Litchfield
Pool

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (57)
"My family and I enjoyed our stay and their hospitality!"
Charming 1870 cape cottage in Litchfield
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (90)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
The House In Highland- Secluded Retreat
Outdoor dining

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (10)
"Very nice location and private."
The House In Highland- Secluded Retreat
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

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

9.6 out of 10, Exceptional, (34)
"Great place for a quiet stay"
$292 nightly
The price is $330
Oct 12 - Oct 13
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Outdoor dining

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

8.8 out of 10, Excellent, (22)
"We were very happy with the accommodations. The cottage was neat, clean and well kept, as was the property. All the amenities were as described. We had a great weekend and would highly recommend this lake house."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Large,Cozy,Bright Apartment, Business Themed.
Interior

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
$573 nightly
The price is $677
Sep 22 - Sep 23
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.
Hickory on Willow Lake
Children's area

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
$539 nightly
The price is $614
Sep 22 - Sep 23
Total with taxes and fees
Hickory on Willow Lake
Lakeview Estate - Chef's Kitchen - NYC Getaway
Property grounds

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (30)
"Happy to have rebooked!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
Smart TV, fireplace

Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

10.0 out of 10, Exceptional, (22)
"Despite the weather we had a great time. The house is very comfortable, well a pointed, nicely updated and was spotless when we arrived. Location is good too!"
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor dining

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (47)
"Wonderful property with a great location."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
Dining

Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

10.0 out of 10, Exceptional, (13)
"Beautiful location and lots of space for a large group. This rental is really about the outdoor space and activities. Would love to return!"
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (16)
"We had a great stay and had everything we needed!"
$799 nightly
The price is $866
Sep 23 - Sep 24
Total with taxes and fees
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!
Smart TV

NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

10.0 out of 10, Exceptional, (13)
"House and property are beautiful. Everything was great!"
NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Property grounds

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

10.0 out of 10, Exceptional, (23)
"Gorgeous views and comfortable stay!"
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
Outdoor dining

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

10.0 out of 10, Exceptional, (4)
"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."
$537 nightly
The price is $624
Oct 7 - Oct 8
Total with taxes and fees
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
YOIN: Whispers of Tranquility, a Zen Retreat
Dining

YOIN: Whispers of Tranquility, a Zen Retreat

YOIN: Whispers of Tranquility, a Zen Retreat
The Queen City Cottage
Exterior

The Queen City Cottage

7.4 out of 10, Good, (16)
"We had a great stay! Good location and the house was very clean. Would definitely stay here again!"
The Queen City Cottage
Enjoy Sip O Sun - Hot Tub, Pizza Oven, Stunning Views, close to dining, shopping, town
Fridge, microwave, oven, stovetop

Enjoy Sip O Sun - Hot Tub, Pizza Oven, Stunning Views, close to dining, shopping, town

10.0 out of 10, Exceptional, (3)
"Easy check in and check out, listing matched property exactly, clean, overall great stay. "
Enjoy Sip O Sun - Hot Tub, Pizza Oven, Stunning Views, close to dining, shopping, town
Waterfront Family Retreat on Candlewood Lake
Outdoor dining

Waterfront Family Retreat on Candlewood Lake

10.0 out of 10, Exceptional, (47)
"Wonderful! Elizabeth and John made everything seamless and enjoyable. Terrific location! "
$1,271 nightly
The price is $1,440
Sep 23 - Sep 24
Total with taxes and fees
Waterfront Family Retreat on Candlewood Lake
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pawling Hotel Reviews

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Staff is excellent starting with the front desk on both evening and day shifts. Clean, convenient, and a great value for the money."
Nanette M 1-night trip
Posted 2 days ago
Quality Inn & Suites Fishkill South near I-84

Find out more about Pawling

Find out more about Pawling

Pawling Vacation Homes information

Number of reviews
460
Accommodation
341 Vacation Homes
Lowest Price
$330
Highest Price
$1,440

Explore a world of travel with Expedia

Explore a world of travel with Expedia