Photo by Marina Timo

Search Cottages in Pawling

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Cottages in Pawling

Cozy Cabin @ Sticks & Stones Farm
Interior

Cozy Cabin @ Sticks & Stones Farm

8.4 out of 10, Very Good, (6)
"Nice clean cabin. Good communication with host."
Cozy Cabin @ Sticks & Stones Farm
Idillic summer getaway in Litchfield Hills, CT.
Exterior

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"Great spot close to Limerock Raceway - private, cute, and a perfect spot to stay! The owners are so nice and accommodating - I couldn’t say nicer things about this place and will be back!"
Idillic summer getaway in Litchfield Hills, CT.
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Beach nearby, beach towels

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (91)
"Property was clean, well appointed, wish we could have stayed a bit longer to enjoy more of the lake & fire pit! "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Pet-friendly Cottage at Historic Millbrook Farm Estate
Interior

Pet-friendly Cottage at Historic Millbrook Farm Estate

10.0 out of 10, Exceptional, (2)
"The house was everything that it is advertised to be. When we arrived, we found it very clean and spacious enough for five adults and two dogs. The hosts were considerate and extremely gracious. The farm is picturesque, chickens and goats look very well cared for and added to the charm. …no worries if you are not an animal lover, the goats and chickens stay far enough away that you can simply not take any notice of them. The beautiful village of Millbrook is just 4 minutes down the road...
Pet-friendly Cottage at Historic Millbrook Farm Estate
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Property grounds

Sweet Dotti's Cottage on Candlewood Lake - 60M NYC

9.6 out of 10, Exceptional, (14)
"Perfect location for families with young children and pets to play in the water with limited boat traffic. Great yard with patios and fire pit for relaxing. Property manager was very responsive and great to work with. Would definitely stay again. Thank you for the great vacation memories!"
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Exterior

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

9.4 out of 10, Exceptional, (6)
"The owners freshly love this place"
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Streamside Cottage @ Sticks & Stones Farm
Miscellaneous

Streamside Cottage @ Sticks & Stones Farm

The price is SAR 640
SAR 1,147 total
includes taxes & fees
26 Jun - 27 Jun
Streamside Cottage @ Sticks & Stones Farm
Magnificent Lake View
Miscellaneous

Magnificent Lake View

2.0 star property
Magnificent Lake View
Dainty New Preston Cottage w/ Dock & Lake Views!
Beach

Dainty New Preston Cottage w/ Dock & Lake Views!

9.0 out of 10, Wonderful, (34)
"Loved our time at this cozy cottage by the lake!! Beautiful views and great antique decor in the cottage!!"
Dainty New Preston Cottage w/ Dock & Lake Views!
Serene Holmes Cottage Near Lakes & Trails!
Interior

Serene Holmes Cottage Near Lakes & Trails!

3.0 star property
Serene Holmes Cottage Near Lakes & Trails!
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
Exterior

Charming, private 2-bedroom cottage on classic New England farm in Washington CT

10.0 out of 10, Exceptional, (2)
"Ashleigh was a great host. Everything you need to know about the property was on the listing - it is on a farm, so you will hear roosters throughout the day. The water pressure is low as described, so we did all take one shower at a time and had no issues.The property itself was very beautiful, spacious and comfortable. We enjoyed being able to see the goats and pigs and Ashleigh was very responsive with all communication before and during the stay. We also greatly enjoyed the bread and eggs...
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
Cozy 2-bedroom Cottage with Access to Bantam Lake
TV, fireplace

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (17)
"The lake and all the homes were beautiful and the house was very clean, organized, and felt like home. "
Cozy 2-bedroom Cottage with Access to Bantam Lake
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Terrace/patio

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

10.0 out of 10, Exceptional, (7)
"Loved staying at this spot when dropping our daughter off for school!"
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Pet-friendly Hopewell Junction Home w/ Pool
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Pet-friendly Hopewell Junction Home w/ Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was so incredible. Not only was it in a quiet nice neighborhood the inside was incredible too. Pool table as well as a pool it was perfect for my stay to have fun and enjoy our time. They were very communicative and welcoming to their house. Everything was comfortable and clean. Can’t say any bad things about this place. Definitely going to book again. I already miss it. "
Pet-friendly Hopewell Junction Home w/ Pool
Two Bedroom Cottage Close To Town
Fridge, microwave, oven, stovetop

Two Bedroom Cottage Close To Town

9.2 out of 10, Wonderful, (21)
"We enjoyed three nights at the cottage. It's beautifully decorated, comfortable, warm and welcoming - a perfect home base for nearby hikes and exploring the area. The large yard was perfect for playing soccer with our child. Renters note: we also had a fabulous meal at nearby restaurant Fern. "
Two Bedroom Cottage Close To Town
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia
Pool

Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia

10.0 out of 10, Exceptional, (1)
"This was the perfect size cottage for 5 of us, with two rooms with queen size beds and one small room with a twin. The setting was very pretty, and the salt water heated pool was a good size and my grandchildren enjoyed swimming in it. We were within walking distance of the small town, and I would recommend staying there."
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia
Lakefront Brewster Vacation Rental w/ Private Dock
TV, fireplace, books

Lakefront Brewster Vacation Rental w/ Private Dock

10.0 out of 10, Exceptional, (5)
"Felt relaxed from first step in the door! Wonderful view, comfortable beds, helpful management, great kitchen! Loved the heated tile floor in main bath! Lots of birds to enjoy with books and binoculars for identifying. "
Lakefront Brewster Vacation Rental w/ Private Dock
This cottage is a 2 bedroom(s), 1 bathrooms, located in Putnam Valley, NY.
Fridge, microwave, oven, stovetop

This cottage is a 2 bedroom(s), 1 bathrooms, located in Putnam Valley, NY.

9.8 out of 10, Exceptional, (18)
"My husband and I were very happy with our stay here. Sara was a communicative and flexible host, even before we arrived. The place matched our expectations from the listing. The cottage was clean, comfortable and had everything we needed for our multiple day stay. "
The price is SAR 703
SAR 1,835 total
includes taxes & fees
17 Jun - 18 Jun
This cottage is a 2 bedroom(s), 1 bathrooms, located in Putnam Valley, NY.
Be in Nature at this Gorgeous Riverfront Cabin
Smart TV, books

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (16)
"Property was as advertised. Clean and nearby places we wanted to visit while, still being out of the way and quiet."
Be in Nature at this Gorgeous Riverfront Cabin
Dreamy Hudson Valley Cottage w/ State Park Views
Interior

Dreamy Hudson Valley Cottage w/ State Park Views

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
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
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Pawling with Expedia?
Booking a cottage in Pawling is as easy as deciding on your travel dates and choosing an ideal place for outdoor relaxation and recreation. From upscale retreats to low-cost properties and cottages that feature perks like a pool, Expedia has something for all tastes. As for the best offers around? We’ve have them as well!
How can I find cheap cottages in Pawling?
Expedia is here to help you easily locate cheap cottages in Pawling. To reserve your ideal stay in a couple of clicks, try out the filter tool to tailor your search results by star rating, amenities and budget.