Smoking-friendly holiday rentals in Fairfield County

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain. Feels like you're way upstate - check out the reviews! Hi-speed WiFi. Next to forest preserve and hiking trails. Furnished deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + pull out couch & twin-size mattress day bed on the porch. Perfect for 2, comfortable for 3, but 4 is probably max comfort since it's a small space. Please note that the road heading up there is steep. A car with AWD is ideal but a sedan will make it up too!

Steele Brook Manor

Kick back and relax in this calm, stylish space. Come enjoy this peaceful setting located on the second floor with a private entrance. The home is tucked away on a dead-end street. You can escape to this lovely spot where the woods are in your backyard and the beautiful sunrise is out your bedroom window! If it's wineries you love Hawk Ridge Winerery 2miles away. The antique trail begins the next town over. Or maybe skiing is on your list just head north under 20 miles and you can be there.

Entire lake house to yourself. Great for groups

This holiday season wake up by a lake and stoke the fireplace. Kitchen is ready to make big family meals and have the house entirely to yourself! new grill, new umbrella. New sleeper couch , new coffee maker. basement cleaned and repaint. Relax, enjoy the view from Screened in porch, pergola fire pit, or deck with gas bbq. Family games in Basement Rec room with pooltable, ping pong, darts.stay a while and remote work in style! Close to Kingston, new paltz, Rosendale. Ask about longer stays.

Gorgeous Suite w/ Private Entrance

Welcome to your private upstairs retreat with its own private entrance and bathroom. This charming efficiency offers a queen bed for restful nights, plus a loveseat sleeper sofa perfect for an adult or two small children. Enjoy the convenience of a mini fridge, coffee maker, and microwave. Step outside your door to our porch sitting area with a grill. Thoughtfully set up to feel both private and inviting, it’s a peaceful space to relax, recharge, and feel right at home during your stay.

Tina luxurious convenient “hidden Gem”

Welcoming all guest for a comfortable stay in a 2-floor walk up apartment accommodating 4-6 people. This unit is the ideal place for your visit whether it is for business, family or a self-rejuvenating stay. A safe place away from home for all occasions. It’s stocked with kitchen cutlery, dishes, WiFi, pots, coffee maker, toaster oven, microwave, refrigerator, and stove. Linen and towels are provided. 12 minutes away from the prudential center and 15-20 minutes away from American Dream.

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. $19 cleaning with or without pets.

Beautiful 3 bedroom Private Home 15 mins from NY

WE HAVE A BUS STOP IN FRONT OF THE HOUSE WHERE YOU CAN CATCH A BUS THAT'LL TAKE YOU TO THE BUS TERMINAL IN TIME SQUARE MANHATTAN, NY. This family friendly guest house can be the perfect get away for you. It is lit well with natural lighting and spacious quarters. All 3 rooms have queen beds and fresh towels. The new American Dream Mall is a 10 minute drive away. Some of the main attractions is the Nickelodeon Amusement Park, Dreamworks WaterPark, Blacklight Minigolf, and Lego-Land.

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

Welcome to Coast to Coast - the perfect getaway from NYC! You may have heard about our new little secret - but you’ll have to come see it for yourself to believe it! Step back into prohibition era Long Island in our hidden speakeasy! Right by Smith Point Beach, we provide accommodations that go above and beyond- this is not your average AirBnB! Soak up the sun at one of LI's top beaches, then enjoy complimentary Netflix, Hulu, cable and more while you shoot pool or play games.

The Design Studio Suite | 2 Beds | Spacious | Luxe

Private one bedroom apartment with modern decor offers everything you need for a short or long term stay. Space includes a full kitchen separate from studio area, & washer + dryer. Studio offers a Queen Sized bed, pull-out bed, workspace, 70 inch Roku Smart TV & hand painted artwork. The Location Less than two miles from Merritt Parkway, near I-95 & East Norwalk train station. One mile away from large shopping center and less than half a mile away from local convenience center.

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.

Wallingford Getaway

ENJOY DAILY CONTINENTAL BREAKFAST INCLUDED WITH minimum two night stay. Experience a cozy stay in our spacious 1300 square foot unit with included breakfast. Choose from muffins, bagels, bars and yogurt. Enjoy a relaxing afternoon with a cup of Java from your own Keurig. This unit features a comfy red electric red reclining couches and a flat screen TV. The kitchen area is equipped with a toaster microwave convection oven and fridge.

Hot Tub Getaway | Game Room + Fireplace

Escape to Blue Barn — your private hot tub + game room getaway, perfect for a fun and relaxing spring stay. Unwind in the year-round hot tub, challenge your group to games, or cozy up by the fireplace after a day out. Whether you’re planning a girls’ weekend, family trip, or low-key celebration, this space is designed for both relaxation and entertainment. ✨ Close enough to everything, yet private enough to truly disconnect.