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Vacation rentals in Pawling

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Top-rated vacation rentals in Pawling

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

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Cabin in Pawling

4.95 out of 5 average rating, 110 reviews

Serene, Peaceful Cabin by the Lake

Take a stroll down to the lake in the crisp morning air, then light the fire and sink into the cherry leather armchair at this rustic log cabin. Touches of soft sage add a soothing side, while patterned rugs and chunky beams keep things homey. Authentic Log cabin, private lake with swimming, kayaking --1000's acres adjacent private land, fishing, hunting-- Enjoy the harvest of the Hudson Valley-- minutes to wineries, Pawling train to NYC, Appalachian trail and hiking, Child safe. Minutes walk to Lake! Private Lake-- We are here to check you in and only if you need us. We respect your privacy and "time-away". The property sits in a private, sprawling lake community minutes from wineries for tastings, Pawling station for trains to New York City, and the Appalachian trail for scenic hiking. Explore Wallkill and Warwick within around an hour's drive. Car, Metro North (train to NYC), Uber, Lyft...

Dec 23 – 30

G$48,799 GYD per night

Home in Carmel Hamlet

4.92 out of 5 average rating, 126 reviews

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.

Aug 29 – Sep 5

G$90,246 GYD per night

Home in Danbury

4.99 out of 5 average rating, 336 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Private 1100 sq. Ft. suite staycation located in a beautiful, safe, quiet neighborhood in DanburyModern Kitchen, One Bathroom, One Luxury Queen Size Bed, 55” Smart TV with Cable/Amazon Prime/Netflix, Apple Cable charger next to bed, Wi-Fi, AC, Heat, Refrigerator, Countertop Oven, Microwave, Electric Hot Plate, Keurig Coffee Maker, Hair Dryer, Iron, Ironing Board, Shampoo, Conditioner, Body Wash. The space is nonsmoking inside and outside the premises including vaping. No children or infants

Sep 4 – 11

G$32,963 GYD per night

Apartment in Lagrangeville

5.0 out of 5 average rating, 127 reviews

Country Oasis | Centrally Located | Strong WiFi

Stay in this serene 2 bedroom apt. right in the heart of the Hudson Valley! Conveniently located only 20 minutes away from Vassar, Marist and the Walkway Over the Hudson! Includes private parking, strong WiFi and a fully equipped kitchen. Enjoy all the greenery from your private deck. Sleep on comfortable queen size beds in each bedroom. Unwind in the living room watching your favorite movies on Netflix. Make this country oasis your home base as you explore all the wonders of the Hudson Valley!

May 9 – 16

G$31,105 GYD per night

Guest suite in Sherman

4.98 out of 5 average rating, 134 reviews

Cozy Scenic New England country retreat w/ hiking

Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey or bike (2 bikes provided) along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian trail & other great hiking. Pets welcome. Inquire about min stay requirements.

Apr 21 – 26

G$30,210 GYD per night

Cabin in New Milford

4.95 out of 5 average rating, 146 reviews

The Cottage on Babbling Brook

Cozy, rustic cottage. Beautifully overlooking Wimsink Brook, with 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.

Nov 29 – Dec 6

G$49,614 GYD per night

Guest suite in Dover Plains

4.91 out of 5 average rating, 262 reviews

Hoppy Hill Farm House

Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Thunder Ridge ski mountain and Daryl Hall’s bar only 15 mins away. Take a ride to near-by towns (Kent, Millbrook, Amenia, Wassaic) for great food, coffee shops, antiques, parks, breweries and vineries.

Jul 9 – 16

G$31,078 GYD per night

Home in Pawling

4.9 out of 5 average rating, 273 reviews

Appalachian Trail House! Easy access to NYC trains

Hike the Appalachian Trail! This is a cozy 3 bedroom, 1 bath, full basement and 3 acres of land. Located in town of Pawling, NY, about 90 minutes from NYC. Walking distance from Appalachian Trail train stop. Enjoy mother nature at it's finest with a short hike up historic Quaker Hill section of the Appalachian Trail. We accept up to 2 well behaved pets under 40 lbs. There is a $50 fee per pet. For companion and service dogs/pets, paperwork must be submitted before stay.

Nov 27 – Dec 4

G$41,473 GYD per night

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Sep 13 – 20

G$24,110 GYD per night

Guesthouse in Mahopac

4.96 out of 5 average rating, 107 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

Sep 6 – 13

G$26,304 GYD per night

Home in Pawling

5.0 out of 5 average rating, 185 reviews

Hobbit House of Pawling

Cozy, one of a kind hobbit house with hot tub! **No children under 12 **No pets (Due to allergies) The ultimate private getaway. 2 bedrooms each with king size beds. 2 bathrooms each with walk in shower. Queen size pull out sofa bed in living room. 3 patios, bbq grill, 2 hammocks, 2 fire pits, electric fireplace in living room. **No parties **No smoking ~Ring Quests upon request at time of booking!

Jul 17 – 24

G$119,717 GYD per night

Apartment in Millbrook

4.93 out of 5 average rating, 205 reviews

Red Tail Ridge

One BR with bath, full kitchen, eating area and living room. Separate entrance and sliding glass door in rear with country views. Located on 12 acre parcel. Close to village of Millbrook (less than 4 miles). We are located in center of Dutchess County. There is great antique shopping, historic sites and some of the finest restaurants and chefs with tastes to suit most everyone. .

Aug 7 – 14

G$26,957 GYD per night

Vacation rentals for every style

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Popular amenities for Pawling vacation rentals

Free parking on premises

Air conditioning

Stay near Pawling's top sights

McKinney & Doyle Fine Foods Cafe44 locals recommend

O'Connor's Public House14 locals recommend

Vinny's Deli & Pasta7 locals recommend

CVS4 locals recommend

Lakeside Park3 locals recommend

Sunflour Bakery4 locals recommend

Other great vacation rentals in Pawling

Cabin in Sherman

4.97 out of 5 average rating, 308 reviews

The Cove Cabin

Oct 31 – Nov 7

G$95,636 GYD per night

Apartment in Pawling

5.0 out of 5 average rating, 15 reviews

Quiet Studio Apartment in Pawling

Nov 8 – 15

G$35,633 GYD per night

Home in Pawling

4.96 out of 5 average rating, 23 reviews

Country Village Getaway

Jan 22 – 29

G$31,613 GYD per night

Guest suite in Pawling

4.92 out of 5 average rating, 62 reviews

Cozy retreat just a short stroll from the village

Jul 4 – 11

G$40,533 GYD per night

Cottage in Pawling

4.98 out of 5 average rating, 82 reviews

Forest Acres Cottage: 10 min to AT/Empire St Trail

Nov 1 – 8

G$37,881 GYD per night

Guest suite in Pawling

4.98 out of 5 average rating, 47 reviews

Charming Private Studio Apartment Retreat

Apr 21 – 26

G$37,988 GYD per night

Cottage in Pawling

5.0 out of 5 average rating, 61 reviews

Twin Lakes Designer A-frame Stone Cottage

Dec 9 – 16

G$75,511 GYD per night

Home in Pawling

4.97 out of 5 average rating, 76 reviews

Farmhouse Oasis in the Hudson Valley, Stream Views

Oct 1 – 8

G$70,676 GYD per night

Destinations to explore