Smoking friendly vacation rentals in Westchester County

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Top-rated smoking friendly rentals in Westchester County

Guests agree: these smoking friendly rentals are highly rated for location, cleanliness, and more.

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Guest suite in Greenwich

NaturallyPreserved Living Next2 Byram River/Gazebo

Stylish apartment@end of a cul de sac circle is a stone path leading to a private flagstone patio & private entrance to a sweet apartment. It has a large living Rm, Full Bath, Kitchen, Brm, in/outdoor cooking, passing through a naturally preserved forest. A stone patio&green yard, a walkway leads to your own private charming Gazebo above Byram River where you can have coffee, practice meditation/yoga, or do work as the entire property has WiFi! In the river you will see fish, turtles, wildlife.

Top guest favorite

Home in Port Chester

5 out of 5 average rating, 19 reviews

3br + game rm abt 45min drive or easy train to NYC

This cozy 3-bedroom Port Chester house (accommodates up to 11 people), offers excellent value, spacious living, and proximity to NYC and Greenwich, CT. A short 10-min walk brings you to the center, the historic Capitol Theatre, & the train to NYC. It's a quick drive to key landmarks and attractions, about 40 mins to NYC, with a train ride to Grand Central taking 45-60 mins. 11-min walk to Capitol Theatre. Perfect for those seeking a quiet, safe neighborhood close to the vibrant city centers.

Home in Stamford

A Farm House Cottage on High Ridge (Pound Ridge)

Step into charm with this restored 1800s farmhouse! Featuring 2 cozy bedrooms, a modern kitchen, sunroom, laundry, and a fireplace with rustic wooden beams. Outside, enjoy a spacious yard with a firepit patio, veggie garden, and room to roam. It’s the perfect blend of old soul and fresh style—a home with heart, character, and plenty of space to make memories. The cottage is a few mins away from charming Pound Ridge, New Cannan and Darien and offering acess to lakes and beaches by short drive.

Home in Glen Cove

4.51 out of 5 average rating, 35 reviews

4 bedroom house perfect for families! near beach!

A GEM in the middle of the most exclusive, neighbourhood, Glen Cove provides a home to families & people who want to experience an actual New York experience. Around 30 mins away from crowded NYC life, this beautiful house has a massive backyard 4 bed 2 bath + bbq grill, hammock, parking, Garden, patio deck to hang out. Close to Sea Cliff beach other scenic beaches, Morgan and Bayville park and Roosevelt Mall. This house provides you with the most luxurious experience and family atmosphere.

Top guest favorite

Camper/RV in Stamford

5 out of 5 average rating, 22 reviews

"Modern RV Escape - Unique Stay w/Firepit Patio".

Welcome. Step into our beautiful RV where every detail has been designed for your enjoyment. Our RV is fully equipped with everything you need for a relaxing stay, including complimentary water bottles, and fast WiFi. Located just 30 miles from NYC, our RV offers the perfect blend of convenience and relaxation. When you're ready to unwind, retreat to your private oasis complete with electricity and water. Park your vehicle in your designated parking spot and enjoy a hassle-free stay.

Top guest favorite

Apartment in Ossining

4.96 out of 5 average rating, 460 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Home in Peekskill

New place to stay

Hudson River Escape • Cabin-Style Townhome

Enjoy an open layout with wood floors, natural light, and central AC. Cozy up by the electric fireplace or head to the finished basement with sofa bed, TV, and ping pong. Just 5 min to Peekskill Station and a 65 min train to Grand Central. Perfect for families, friends, or remote work, this cabin style retreat offers space to gather, watch movies, and relax in comfort. (Pet friendly too!) The home exterior is camera secured, plus 1 indoor camera in the common living room area!

Superhost

Tiny home in Chappaqua

4.88 out of 5 average rating, 51 reviews

Cozy tiny log cabin on 13 acres

Tiny rustic cabin located in the woods. Large screen TV and Wi-Fi. No stove but will provide cooktop and toaster. Full bathroom with shower. People love the back deck to enjoy their morning coffee and to watch for wildlife. One bedroom with comfy queen bed and fan. All linens and towels supplied. Please be aware this is a rustic beautiful site. Trails in the back and very close to rail trail. Mini splits will keep you toasty warm in the winter and ice cold in the summer.

Apartment in Tenafly

Prime tenafly, perfect 2 bed

Spacious, bright 2 bedroom 1 bathroom in walking distance from main bus terminal in downtown tenafly. Walk in kitchen, renovated bathroom and a big living room with dining room space make this 2b/1b apartment the ideal short term stay. Great light, very quiet and property includes parking spaces for 2 car, a private washer and dryer in the basement and views of downtown. This apartment is a 4 minute walk from the downtown tenafly hub, and a 30 minute bus to manhattan.

Superhost

Apartment in Yonkers

4.78 out of 5 average rating, 176 reviews

Apartment in Yonkers

Fully renovated private 1 bedroom apartment. Forget all of your worries at this stylish, spacious, 420 friendly, centrally-located place just 10 minutes walk to Yonkers Boardwalk and train station. 1 bedroom space, can fit 3 adults comfortably features 1 queen bed and 1 queen pull out sofa. full bathroom and full kitchen WiFi and free streaming services on 50in HDTV free street parking and paid private parking at 99 vark st (3 min walk)

Apartment in Yonkers

4.7 out of 5 average rating, 247 reviews

A Serene Yonkers Escape

Ground level apartment in the north side of Yonkers. About 30 minute commute to the city. About 7 minutes away from the Yonkers waterfront. St. Johns hospital within walking distance. This stay is perfect for those who need a nice peaceful place to crash and not limited to those who are looking for a long term stay. Cameras located on the outside of the premises only. BBQ and outdoor furniture can be used for an additional fee.

Tent in Mamaroneck

New place to stay

River tent, 35 min train ride from Manhattan!

Enjoy this unique experience; Your own tent on the Mamaroneck River. 35 minutes from NYC ( by train) NO car needed, all is walkable! It is your own little escape in nature but also in a little village with great restaurants, movies , theater, yoga classes, and Harbor Island. You can just escape The City and recharge yourself.