Holiday rentals with a fireplace in Shelter Island

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Top-rated Accommodation with Fireplace in Shelter Island

Guests agree: these holiday homes with a fireplace are highly rated for location, cleanliness and more.

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Guest favourite

Home in East Quogue

5 out of 5 average rating, 80 reviews

Cozy beach themed & newly renovated home

Our house was recently fully renovated and includes 5 private bedrooms, 2 full baths, a fireplace, full kitchen, and a multitude of outdoor amenities such as a heated pool, hot tub, outdoor bathroom, patio with grill, fire pit, half court basketball court, and a lounge area to name a few. The hot tub is open year round, the pool is open generally from Memorial Day to Labor Day, depending on weather. Located just a quick 10 minute drive to the beach, 15 minutes to Riverhead for shopping, and close to farms and vineyards, there is plenty to help keep busy when heading out for the day. Also very close to restaurants and local shopping to help get a real taste of the Hamptons. We are happy to make recommendations upon booking!

Superhost

Home in Hampton Bays

4.88 out of 5 average rating, 226 reviews

Nautical Cottage Near Beach, Wineries, Golf, Shops

Coastal themed cottage located in the center of The Hamptons. Super Hosts! Great WiFi. Bright & comfortable space! Cowfish/Canoe Place Inn closeby! Near WINERIES, BEACHES, GOLF, WATERFRONT RESTAURANTS, & SHOPPING. 4 bedroom areas 2 full baths & outdoor shower. Spacious backyard w/ fire pit & deck w/ string lights. Lot's to do each season for couples, friends, coworkers & families. Everything you need & want in a Hampton's home. Large screen TVs/Roku, Foosball. Access to loft bedroom by ladder.

Superhost

Cottage in North Fork

4.92 out of 5 average rating, 52 reviews

Beautiful cottage on East End

Beautiful cozy cottage in the heart of wine country. Perfect for a family or a couples weekend away. Close to wineries, breweries, beach, outlets, restaurants, all that the North Fork has to offer. King master with bath two queen size bedrooms all on one floor Additional bathroom. Wood burning fireplace, washer dryer Absolutely NO PETS!!! Families Or rentals for people 30 and over Please be aware we require at least a 5 night stay during the summer months. There IS NOT a pool on the property

Top Guest favourite

Cottage in Sag Harbor

5 out of 5 average rating, 49 reviews

Luxury Gem At The Heart of Sag Harbor Village

An impeccably renovated, luxury cottage at the heart of Sag Harbor village. Walkable within minutes to the downtown shops, restaurants, marinas and local beach! In one of the most coveted historic streets, enjoy this two-bedroom house, its large living & dining rooms, two fireplaces, designer kitchen (and latest appliances). Countless details and gorgeous wide planked floors, mixed with technology throughout the house. The private backyard has a brick patio, landscaped garden and outdoor shower.

Guest favourite

Home in Southampton

4.9 out of 5 average rating, 20 reviews

Southampton Shinnecock Hills SummerFall 25 rentals

Southampton Shinnecock Hills Summer Rental 2024. Lovely brick home with private parking with a wrap around deck. 3 bedrooms, 6 beds, 2.5 baths, living room, dining room, and kitchen. Huge T.V., fireplace, and indoor barbecue. Brand new washer and clothes dryer. Big backyard. Near Coopers Beach, Tiana Beach, Ponguogue Beach, and Meshutt Beach. Plenty of parking for 4 cars. Vis NOTE: PLEASE REFER TO "OTHER THINGS TO NOTE" REGARDING NYS SALES TAX/SUFFOLK COUNTY HOTEL/MOTEL OCCUPANCY TAX

Guest favourite

Home in North Fork

4.98 out of 5 average rating, 100 reviews

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's, and recently & lovingly fully renovated and restored. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

Superhost

Home in Shirley

4.78 out of 5 average rating, 312 reviews

Beautiful home with Game Room

Beautiful home with modern farmhouse decor located near the beach, the vineyards and the Hamptons! We have board games, a ping pong table, a poker table and a tv with Hulu! Hangout by the firepit on chilly nights or stay in the Central A/C on those hot days. Play outside with the kids or watch them play from the hammock. Grill some burgers and hang on the back patio. Everything you need for a fantastic stay. Come check it out! We promise you won’t be disappointed :) *No Parties*

Guest favourite

Home in North Fork

4.94 out of 5 average rating, 127 reviews

⭐️Modern Farmhouse Long Island Wine Country🍷

Long Island’s North fork Long Island Wineries. Luxurious, clean , modern peaceful farmhouse. Top of the line fully stocked kitchen, stainless steel appliances, granite countertops. Keurig Coffee maker, Tea, Hot Coco. Coffee grinder . 2 fully stocked Spa like bathrooms w/ luxurious towels .4 Lg. Bedrooms. w/ luxurious linens .Cozy fireplace in Living room. Spacious dining room. Close to Farms, Wineries, Corn Mazes, Haunted Attractions, Sunflower Mazes. Pumpkin 🎃 Apple 🍎 Picking

Guest favourite

Tiny home in Mastic

4.94 out of 5 average rating, 115 reviews

Cozy craftsman style home close to beaches

Feel refreshed when you stay in this rustic gem. 10 minutes from the fire island beaches this newly renovated home will take your breath away. 20 minutes from local wineries theres no shortage of things to do. This is a single dwelling home. There is a basement apartment with a separate entrance. The tenant does not have access to the house. Everything pictured is yours to use! Kick your feet up and enjoy the details of this handcrafted home. Tree house inside and out!

Top Guest favourite

Home in East Hampton

4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

Guest favourite

Home in North Fork

4.94 out of 5 average rating, 33 reviews

Bailey House

The Bailey House is a 1,900 square foot, fully renovated, 2 bed 2 bath home, with a modern rustic style. It has a working fireplace, baby grand piano, updated appliances, large smart tv and built in bluetooth speakers throughout. The backyard is fully fenced in with a pool, koi pond and barn. The barn has a wood burning stove. It is not insulated and has barn doors that do not fully seal it off from the elements. not included in square footage.

Guest favourite

Home in North Fork

4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.