Vacation rentals with a fireplace in Southold

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Top-rated fireplace rentals in Southold

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Guest favorite

A heated pool is surrounded by lounge chairs, inviting relaxation on warm days. Lush greenery and tasteful landscaping create a serene outdoor space, while a wooden deck offers an elevated view of the pool area, enhancing the overall ambiance of the backyard.

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

An open-plan living space features a cozy seating area with a sofa and large windows allowing natural light. A dining table with white chairs is situated next to a marble countertop kitchen, equipped with modern appliances. A ladder provides access to an upper loft area.

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.

Top guest favorite

A spacious living area features a light-colored sectional sofa and a round coffee table. A modern fireplace with a flame provides warmth, while natural light enters through large windows. Neutral colored rugs bring a sense of comfort and style to the room.

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 favorite

A spacious bedroom features a large bed with a gray blanket and decorative pillows. A cream-colored sofa sits near the window, providing natural light. The light walls and chair rail contribute to a calming atmosphere, while a fireplace is positioned against the wall.

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

A modern kitchen features white cabinets and wood accents. A wooden island with seating for four is positioned in the center, complemented by a stylish pendant light above. Stainless steel appliances and an open layout create a welcoming cooking environment.

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 favorite

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 favorite

The interior features a bright, open space with wooden beams and rustic decor. A comfortable couch with a plaid throw faces a wall-mounted TV. A staircase with unique railings leads to the upper level, while a dining area is visible to the side.

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 favorite

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

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 favorite

A three-level home is surrounded by lush greenery, featuring large glass doors that open to balconies. An above-ground pool is visible within the fenced yard, complemented by a spacious outdoor area. The property embodies a coastal aesthetic with a combination of stone and wood exterior.

Vacation home in Westbrook

4.88 out of 5 average rating, 33 reviews

Modern Coastal Home with Pool

Welcome to Salty Marsh! This stylish 3-level home is perfect for just about anyone looking for beautiful sunsets, coastal vibes, and a comfortable and unique vacation. Every inch of this space has been thoughtfully designed and decorated to make you feel at home while on vacation. A perfect location for a family gathering, a few couples get away, girls weekend or any excuse to escape. This unique property offers 3-levels of living with two equipped kitchens.

Top guest favorite

Home in Miller Place

4.96 out of 5 average rating, 56 reviews

Cozy Cottage Close to the Sound

Enjoy the winter water view of Long Island Sound in this cozy completely renovated getaway. TV's in every room. ensuite bathroom in master bedroom with king bed . All new everything including bathrooms with pebble floored showers . Wood burning fireplace and outdoor firepit. New refrigerator with beverage draw and lots of other amenities. Deck and an enclosed porch. Close to Cedar Beach, Mt Sinai Harbor , Port Jefferson Ferry, and Stony Brook University

Guest favorite

A serene backyard features a inviting pool surrounded by lush green grass and vibrant plant life. A natural stone sits at the pool’s edge, and a rustic barn is positioned to the side, suggesting a peaceful outdoor retreat.

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 favorite

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.