Vacation rentals in Pawling

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Quick stats about vacation rentals in Pawling

Nightly prices starting at
Pawling vacation rentals start at $143 CAD per night before taxes and fees
Verified guest reviews
Over 220 verified reviews to help you choose
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Pawling rentals
4.9 Average rating
Pawling stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Pawling

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite

A view from the cozy bed showcases a window adorned with soft curtains. Outside, lush greenery and vibrant pink flowers are visible through the glass, enhancing the connection to nature.

Guest suite in Pawling

Cozy retreat just a short stroll from the village

The Colonel Vanderburgh Suite is a private, cozy, efficient room with private bathroom that is separate from the rest of the main house. Guests do not have access to the main house. There is NO kitchen. You can come and go thru your private entrance and enjoy all the amenities that the room has to offer. QFree Wi-Fi, brand new Smart TV, coffee maker, mini fridge, Beekman 1802 toiletries, linens, robes, hair dryer, etc. Feel free to roam the property, use the fire pits and relax by the stream

LocationFamilyGetting around

4.94 out of 5 average rating, 133 reviews

Top guest favourite

A sunlit enclosed sunroom features a curved sectional sofa adorned with decorative pillows and a central wooden table. Large windows invite natural light, offering views of the backyard. A rocking chair and potted plant add a cozy touch to the inviting space.

Home in Dover Plains

Hillside Grove

Country hillside retreat. Expansive outdoor patio area complete with Blackstone grill and hot tub. A cozy deck with casual seating nestled amongst the trees and an exquisite natural stone fire pit with six adirondack chairs. An enclosed sunroom overlooking expansive property and sunset. A large harvest table with seating for 8 in the main dining area for more formal gatherings. Fully equipped, recently renovated kitchen and a sitting room for enjoying morning coffee or tea. Large family room.

LocationFamilyComfort

4.96 out of 5 average rating, 108 reviews

Guest favourite

A dining area is shown with a round wooden table at the center, adorned with a vase of flowers. Large glass windows frame a serene lakeside view, with blooming flowers in the foreground and lush greenery. Soft sunlight reflects off the water, creating a tranquil atmosphere.

Home in Carmel Hamlet

Lux Bungalow on the Lake

Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.

ValueFamilyHeating

4.92 out of 5 average rating, 233 reviews

Superhost

Apartment in Pawling

Peaceful Pawling Getaway

Your Peaceful Pawling Getaway awaits: a spacious 3-bedroom apartment in historic Pawling, NY. Ideal for families, friends, couples, and remote workers. Featuring 3 bedrooms, 1.5 bathrooms, living area with kitchen essentials, and private entrance. Walking distance to Pawling village and train station. Close to the famous 'Daryl's House', a ski resort, and Appalachian/Empire State hiking trails. Great for nature retreats, village stays, or quiet weekends; perfect for short stays or longer visits.

LocationCleanlinessBathroom

4.83 out of 5 average rating, 6 reviews

Top guest favourite

A spacious studio apartment features large windows allowing natural light to fill the room. A comfortable king size bed is positioned alongside a cozy seating area with a sofa and coffee table. A textured area rug covers the hardwood floor, adding warmth to the space.

Apartment in Pawling

Quiet Studio Apartment in Pawling

For getaways or visiting the area, this peaceful sanctuary awaits your arrival in Pawling. A fresh clean studio apartment with idyllic views of the forest, stone walls, and distant mountains. Awake to the sound of birds and beautiful sites. With a king size bed, kitchenette, desk, Smart TV, WIFI, full bath with walk-in shower. Big sliding glass door to private deck overlooking native landscaping. 1 mile to village for restaurants, bakeries, & night spots. 7 min by taxi to Darryl's House Club.

FamilyLocationDecor

5.0 out of 5 average rating, 155 reviews

Superhost

Home in Pawling

Harlem Valley Hideout - Artsy Home with Pool & Ten

Marvel at the playful design of this 2-Bed, 3.5-Bath mid-century cottage with a nursery, just 1hr 40min from NYC. Perfect for art lovers & families alike, this one-of-a-kind renovated home is full of life, bursting with color & dynamic designs. Highlights include a chef's kitchen, pool, fireplace, firepit & a private tennis court—an ideal family getaway. Nearby towns: Wassaic, NY (25mins), Kent, CT (25mins), Millbrook (30mins), New Preston, CT (35mins), Beacon (35mins), Poughkeepsie (35mins)

FamilyLocationCheck-in

4.8 out of 5 average rating, 10 reviews

Top guest favourite

Apartment in Holmes

Top Side

Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

ValueFamilyCheckout

5.0 out of 5 average rating, 153 reviews

Guest favourite

A charming two-story cottage is surrounded by trees, with a lush green hillside in the backdrop. The driveway leads to a garage with two entrance doors. An outdoor staircase ascends to the living area, illuminated by dappled sunlight filtering through the leaves.

Cottage in Pawling

Forest Acres Cottage: Appalachian/Empire St Trail!

This charming, stand alone cottage was completely renovated to welcome you to the picturesque Hudson Valley. Secluded porch overlooks a peaceful forest. Fast wi-fi, high end mattresses, cozy linens, fully stocked cook's kitchen and gas stove. Located on one of the area's most scenic roads yet close to major highways, Metro-North railroad and Hudson Valley delights. Three Empire State Rail Trail and two Appalachian access points merely 5-10 minute drive. Bring your bikes and walking shoes!

FamilyValueTV

4.97 out of 5 average rating, 117 reviews

Top guest favourite

A spacious living area features vaulted ceilings and large windows offering scenic views of the outdoors. Comfortable sofas are arranged around a textured rug and a coffee table. A stone fireplace adds warmth, while plants bring a touch of nature indoors.

Cabin in Holmes

Spa Cabin with 2 Suites & Hot Tub

Welcome to Your Dream Retreat! Enjoy our custom-built cabin on a scenic 5-acre lot in the Mid Hudson. With 5 bedrooms, 3.5 baths, & curated amenities, this home blends comfort & style for an unforgettable stay. Whether soaking in the hot tub, strolling nearby trails, or gathering around the fire pit, our cabin is your perfect home away from home. We’re proud to be in the top 1% of Airbnb listings—earned through thoughtful touches, warm hospitality & a space guests love coming back to.

ValueLocationHospitality

4.98 out of 5 average rating, 112 reviews

Guest favourite

An outdoor seating area is featured with two ornate egg chairs and a spacious sofa. The furniture is complemented by colorful cushions, and a geometric patterned rug is placed underneath. A stone fireplace is visible in the background, surrounded by trees.

Home in New Fairfield

Hilltop Retreat- Lakefront with Dock

Enjoy all that Candlewood Lake and Squantz Pond State Park have to offer in the comfort of our home. Come reconnect with love ones and relax in the serene surroundings. This waterfront property has a private dock, features 2 bedrooms, 2 full baths, and views from almost every room in the home, plenty of indoor and outdoor entertaining space and a wood burning fireplaces to keep toasty during chilly evenings. Toiletries, all linens are provided. Please read house rules before booking.

LocationFamilyGrill

4.95 out of 5 average rating, 107 reviews

Top guest favourite

A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.

Cottage in New Milford

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

ValueFamilyLong stay

4.95 out of 5 average rating, 259 reviews

Top guest favourite

A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.

Cabin in Sherman

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

ValueFamilyIndoor spaces

4.96 out of 5 average rating, 467 reviews