Smoking friendly holiday rentals in Westchester County

Greenwich Hideaway Pool, Deck, Theater, Near NYC

Recharge or work remotely at this peaceful Greenwich retreat — a private ranch with a home theater living room, spacious deck, and brand new 24’ pool. Just ½ mile from the Merritt/Hutchinson Pkwys, 10 mins from Greenwich Ave & train, and 3 miles from Westchester Airport. Tucked at the end of a quiet cul-de-sac with a large backyard — perfect for relaxing or getting things done. Summer Specials ✅ 6-Night Weekday Stay (Sun–Fri) → $2,100 flat ✅ 7-Night Full Week Stay (Incl.Weekend) → $2,400 flat

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.

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.

Best hotel alternative for big group, near train

Location, location, location. Nestled in downtown Greenwich, this charming kid-friendly 4-BR house/2.5 bath offers prime location w/ 2 free parking spots. Enjoy a full kitchen, washer/dryer, private entrance, garden & patio. Steps away from Greenwich train station, Greenwich Ave, & key landmarks. Drive minutes to other parks & Greenwich Hospital. Easy access to NYC via train (45-55 mins to Grand Central) & via 95. Experience the best of downtown Greenwich with the convenience of home.

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.

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.

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.

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.

3br English Cottage in Tarrytown

Tucked away on a secluded lane, this enchanting Cotswold Tudor just steps from the village is set in one of Tarrytowns most picturesque neighborhoods. New kitchen, hardwood floors, WBFP, views of Hudson River, and only 25 miles to Manhattan.