Photo by Marina Timo

Search Cottages in Pawling

Start date: Check-in selected.
End date: Check-out
    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

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
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.
Cozy 2-bedroom Cottage with Access to Bantam Lake
Property grounds

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (18)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake
Be in Nature at this Gorgeous Riverfront Cabin
Exterior

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (20)
"An ideal retreat. The modern cabin offered serene surroundings with stunning views of the woods and creek. The property was well-maintained, and the property manager was highly responsive. A perfect choice for a peaceful and refreshing getaway."
Be in Nature at this Gorgeous Riverfront Cabin
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia
Exterior

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

10.0 out of 10, Exceptional, (2)
"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
Magnificent Lake View
Property grounds

Magnificent Lake View

2.0 star property
Magnificent Lake View
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Property grounds

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

10.0 out of 10, Exceptional, (7)
"We loved our stay at this stylish and cozy cottage. The views are so pretty and the interior style invites relaxation. "
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Lakefront Brewster Vacation Rental w/ Private Dock
Exterior

Lakefront Brewster Vacation Rental w/ Private Dock

10.0 out of 10, Exceptional, (10)
"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
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, (4)
"Four of us were in town for a family party and really enjoyed our stay at the cottage. It’s peaceful, cozy, very well appointed, and wonderfully decorated. We also enjoyed a visit with the goats! "
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
Scenic Hudson Valley Getaway • Farms & Vineyards
Exterior

Scenic Hudson Valley Getaway • Farms & Vineyards

10.0 out of 10, Exceptional, (1)
"It was exactly what my family and I needed. A cozy, quiet place to stay with mountain views. The owner is responsive and communicates quickly. Will come back again."
Scenic Hudson Valley Getaway • Farms & Vineyards
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, (10)
"The owners freshly love this place"
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Two Bedroom Cottage Close To Town
Exterior

Two Bedroom Cottage Close To Town

9.2 out of 10, Wonderful, (23)
"The house had everything we needed. The full kitchen served us well, the beds were comfortable, and the showers were great!"
Two Bedroom Cottage Close To Town
Pet-friendly Hopewell Junction Home w/ Pool
Outdoor dining

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
Relaxing, Charming & Best Location!
Exterior

Relaxing, Charming & Best Location!

10.0 out of 10, Exceptional, (1)
"The property is amazing. The house is beautiful and very inviting and comfortable. It was easy to locate. Even though the property was older with loads of charm it was updated with many modern conveniences. The owner stayed in contact to make sure we had everything we needed. We would stay again. "
Relaxing, Charming & Best Location!
Serene Holmes Cottage Near Lakes & Trails!
Front of property

Serene Holmes Cottage Near Lakes & Trails!

3.0 star property
Serene Holmes Cottage Near Lakes & Trails!
Peaceful Cottage with Grill | Walk to Lake
Exterior

Peaceful Cottage with Grill | Walk to Lake

9.8 out of 10, Exceptional, (21)
"This property was great. Clean, roomy and about 1/2 hour from West Point."
The price is HK$1,310
HK$3,683 total
includes taxes & fees
10 Sept - 11 Sept
Peaceful Cottage with Grill | Walk to Lake
Fire Pit + On-site Pond: Hudson Valley Home!
Interior

Fire Pit + On-site Pond: Hudson Valley Home!

3.0 star property
Fire Pit + On-site Pond: Hudson Valley Home!
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
Lakefront Brewster Vacation Rental w/ Private Dock
Interior

Lakefront Brewster Vacation Rental w/ Private Dock

3.0 star property
Lakefront Brewster Vacation Rental w/ Private Dock
Charming Sharon Dwelling w/ Deck & Fire Pit!
Exterior

Charming Sharon Dwelling w/ Deck & Fire Pit!

3.0 star property
Charming Sharon Dwelling w/ Deck & Fire Pit!
Modern Escape w/ Fire Pit, Near Lake Waramaug
Interior

Modern Escape w/ Fire Pit, Near Lake Waramaug

3.0 star property
Modern Escape w/ Fire Pit, Near Lake Waramaug
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

Top Pawling Hotel Reviews

Find out more about Pawling

Find out more about Pawling

Pawling Cottages information

Number of reviews
Accommodation
72 Cottages
Lowest Price
HK$1,310
Highest Price
HK$1,310

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.
What is there to do in Pawling near my cottage?
The perfect travel accessory is a well-planned to-do list. John Kane House is an excellent place to kick-start your exploration of Pawling.