Smoking-friendly holiday rentals in Long Island

4.9 out of 5 average rating, 111 reviews

Home in East Hampton

Serene, pristine + private Hamptons, near it all

Get away to your private, serene, Hamptons home, any time of year! Enjoy the peace + serenity in your large home, surrounded by nature + calmness. Curl up to the wood burning fireplace, stream on your 80' TV, enjoy the large book collection. Spark up the BBQ + firepit under the starry sky! Walk 1 block to the waterfront/marina. You'll be 3-10 minutes to beaches, cafes, Main St. East Hampton + Amagansett + so much more! During summer, swim all day, enjoy waterfront dining just up the block.

4.87 out of 5 average rating, 67 reviews

A cozy corner of the studio features a green couch adorned with a textured pillow and a small table. A chandelier casts a warm glow, while tall, patterned curtains frame the window. Decorative art pieces, including a guitar, personalize the space.

Home in Hoboken

Cozy Studio in the Heart of Hoboken.

My studio apartment is in the most desirable area of Hoboken New Jersey. Three blocks down you can take a ferry across the Hudson River or take a bus to the PATH station 10 blocks down anywhere you want to go. Trader Joe’s three blocks down and restaurants galore.. right outside the door! It’s a small studio apartment with a double bed loft with a ladder and an extremely comfortable couch. The movie theater, shopping ice skating rink are all minutes away walk. Twelve foot ceilings make it big.

4.97 out of 5 average rating, 141 reviews

A rustic log cabin is framed by tall trees, showcasing a spacious porch with a wooden railing. The front door features two circular glass panels, allowing natural light to enter the home. Lush greenery surrounds the property, enhancing its secluded appearance.

Cabin in Warwick

Magnificent Log Cabin Getaway with Private Lake

Enjoy the comforts of a magnificent log cabin set on six private acres in the Hudson Valley! Newly furnished, this 4-bedroom home comes with multiple living rooms, an indoor wood-burning stove, sauna, pool table, theater room, large private pond with dock, fire pit, and more! You'll be minutes away from restaurants, wineries, breweries, and activities for all members of your group. Near many trails, Greenwood Lake, and Mount Peter. Also a perfect getaway for skiing. Come escape and relax!

4.98 out of 5 average rating, 59 reviews

Apartment in Stony Point

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.

4.96 out of 5 average rating, 492 reviews

A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.

Apartment in Ossining

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.

4.91 out of 5 average rating, 89 reviews

A spacious living area features a comfortable blue sectional sofa adorned with colorful accent pillows. A dining table with light-colored chairs is visible, complemented by a modern kitchen in the background. Artwork is displayed on the wall above, enhancing the vibrant atmosphere.

Home in Mastic Beach

“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath

Discover the “Cool House” This is the coolest waterfront getaway on the south shore of Long Island! Waking up to beautiful sunrises, dinners with a sunset every night & dancing under the stars is a lifestyle your family & friends will cherish forever. The perfect escape from NYC, minutes from the Atlantic Ocean & just a short drive to the Hamptons! This meticulously renovated oasis is the perfect living & entertaining space, a trendy retro beach vibe designed for fun or relaxation.

4.94 out of 5 average rating, 260 reviews

The open living area features a custom slate pool table with a vibrant arrangement of billiard balls. A modern kitchen is visible in the background, including sleek cabinetry and a refrigerator. A tasteful seating area includes a fireplace and a large wall-mounted television.

Home in Shirley

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.

4.98 out of 5 average rating, 44 reviews

A modern living space features a leather sofa and two textured chairs surrounding a glass coffee table. A well-lit kitchen is visible in the background, with an island showcasing decorative plants. Hardwood flooring runs throughout the open area, enhancing the spacious feel.

Apartment in Norwalk

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.

4.83 out of 5 average rating, 30 reviews

The image presents a coastal view featuring a well-maintained property adjacent to the shoreline. The sky displays a gradient of colors at sunset, and gentle waves can be seen lapping against the rocky beach. Surrounding greenery complements the tranquil setting.

Home in Greenport

North Fork Sound Front Home with Pool

This Long Island Sound front property on nearly three acres of land with an inground, custom designed, gunite pool is the perfect vacation home. Walk down the ramp to your private beach for a kayak, paddle board or swim in the summer and enjoy a luxurious outdoor shower afterwards. In the fall and winter months, enjoy the extensive book collection and stay cozy by the fireplaces. Spacious and bright, this home has a unique aesthetic and can accommodate 8 guests comfortably.

4.89 out of 5 average rating, 57 reviews

An inviting interior space features a rustic bar area with three metal stools, complemented by a wooden countertop. A soft circular rug rests on the floor, and a decorative armchair is positioned nearby. Natural light filters through the window, enhancing the cabin's cozy atmosphere.

Tiny home in Chappaqua

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.

4.84 out of 5 average rating, 260 reviews

A well-lit bedroom features a spacious bed with blue bedding, positioned against a wall with two windows. Two bedside lamps provide soft lighting. A colorful area rug adds warmth to the wooden floor, while a wall art piece displaying a map is visible.

Home in Brooklyn

2 Bedroom Guest Suite With Private Entrance

Experience Crown Heights and East Flatbush in your own private 2 bedrooms unit with living room, kitchen, restroom and separate entrance. You only share the backyard if you want to use it. Peaceful neighborhood with nearby grocery store, pharmacy, pizza and bagel shop, public playground are 1-2 blocks away, jacuzzi bathtub, flat screen TV, Premium Netflix. Close to Brooklyn children museum, Prospect park, Botanical gardens and more.