Vacation rentals with a fireplace in Southold

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Popular amenities for Southold fireplace rentals

House rentals with a fireplace

Guest favorite
A charming home is showcased, featuring cedar shake siding and a sloped roof. A wooden deck leads to the entrance, flanked by large front steps. Lush greenery borders the property, while a pebble pathway and manicured grass add texture to the welcoming outdoor space.
Home in Sag Harbor
5 out of 5 average rating, 5 reviews

Sag Harbor 3 bedrooms, Heated Pool

MichaelRating, 5 stars8 months ago
Just stayed for one night but was a beautiful place. Nice and private, set back from the road so it felt like you were completely secluded. The house was nice and cozy and clean!
Guest favorite
The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars3 weeks ago
It was wonderful stay and I’d go back anytime
Top guest favorite
A bright living area features comfortable seating on a light gray couch and armchair, accompanied by a decorative coffee table. A shelf filled with books and decor pieces adorns the blue wall. Natural light floods the room through large windows, complemented by indoor plants.
Home in North Fork
5 out of 5 average rating, 14 reviews

Peaceful Guesthouse

CherylRating, 5 stars1 week ago
Very nice house with lots of room to relax and a well-stocked kitchen to cook. The house was clean and the beds were comfortable. The neighborhood is quiet and close to so much! When we had a question, Ellen answered with a call within minutes. She was the perfect host!
Guest favorite
A stone pathway meanders through a lush garden, bordered by vibrant greenery and flowering plants. The charming home is partially visible, with warm light emanating from its windows, nestled amidst the natural surroundings.
Home in Hampton Bays
4.98 out of 5 average rating, 46 reviews

Sophisticated and Sweet

KarenRating, 5 stars8 months ago
This location was exactly like the picture but only better. The location is great and there's a lot to do in the area. The Kitchen was well stocked with essentials and had many appliances. All of the towels and linens were included and clean. Worth your visit.
Top guest favorite
A charming single-story house features a classic shingle exterior with a brick chimney. A spacious front deck is bordered by white railings and overlooks a manicured lawn surrounded by trees. Soft sunlight filters through the leaves, enhancing the serene setting.
Home in East Hampton
4.95 out of 5 average rating, 230 reviews

Private beach, fully updated house, on 2 acres.

CaitlynRating, 5 stars2 months ago
This home is beautiful and so spacious! Proximity to East Hampton and Springs, yet very private and peaceful. Couldn’t recommend enough!
Guest favorite
A well-maintained pool area is set against a backdrop of lush greenery, featuring a shimmering pool surrounded by lounge chairs. Sun umbrellas provide shaded spots, and a trampoline is visible in the distance, adding to the outdoor recreational space.
Home in Hampton Bays
5 out of 5 average rating, 9 reviews

Hampton Bays Hideaway!

Jho’LeeRating, 5 stars22 months ago
We had another great stay at Claudia's place! This was our third visit to this location, and likely not our last. Thank you!!
Top guest favorite
A bright kitchen features sleek white cabinetry and stainless steel appliances. A circular table sits centrally, complemented by a small potted plant. Natural light filters through the patterned window treatment, enhancing the modern atmosphere of the space.
Home in Westhampton Beach
5 out of 5 average rating, 18 reviews

Charming Home in WestHampton Beach

EileenRating, 5 stars7 months ago
Jenny's home was perfect for our family reunion in Quogue. Super clean and comfortable. If you like to cook, the kitchen has plenty of high quality pots and pans, dishes, sharp knives , wine glasses etc. Beautiful and private backyard was perfect for early morning coffee. I highly recommend and will definitely come back.
Guest favorite
The exterior of the Scandinavian cottage features a modern design with wooden paneling and a metal roof. Lush green grass surrounds the building, with mature trees providing shade. Outdoor seating is positioned beside the structure, contributing to a serene outdoor atmosphere.
Home in Southampton
4.94 out of 5 average rating, 50 reviews

Scandinavian Cottage

JacobRating, 5 stars4 months ago
The Scandinavian Cottage in Southampton was a delightful retreat. It was immaculately clean, well-appointed, and ideally located. I highly recommend it!

Apartment rentals with a fireplace

Top guest favorite
A cozy living area features wood-paneled walls and abundant natural light from four windows. A circular dining table accompanied by four chairs is positioned near the entrance, while a gray sofa and a side table provide additional seating options. A decorative wall art piece enhances the space.
Apartment in Southampton
5 out of 5 average rating, 8 reviews

Sugarloaf Annex

DianaRating, 5 stars3 months ago
Really cute and clean place, so happy we stayed here! It was perfect little place for a getaway to relax, even in the winter months. Everything inside was up to date and it had everything we needed. It even looked better in real life than the photos. Highly recommend!
A tranquil backyard features a winding pool with clear blue water, bordered by a stone patio. Lush greenery and organized seating areas complement the serene environment, while well-maintained landscaping adds to the overall appeal.
Apartment in Medford
5 out of 5 average rating, 4 reviews

Medford Seclusive Getaway Nice !

SandraRating, 5 stars2 weeks ago
Hosts were very pleasant and accommodating. We would highly recommend them and would stay there again.
Guest favorite
The living area features an arrangement of antique furnishings, including a cozy sofa and various seating options. A rustic brick fireplace serves as a focal point with a decorative mirror above it. Natural light floods the space through large windows, enhancing the inviting atmosphere.
Apartment in Sag Harbor
4.93 out of 5 average rating, 153 reviews

Whaling Captain Pierson's Cottage

AngeloRating, 5 stars4 months ago
Paris is a wonderful host. His property and cottage is a perfect retreat for two. Charming accommodations with a beautiful view and an easy walk to town. We’ll be back soon! Angelo C.
Guest favorite
The living area features a light-filled space with large windows, allowing natural light to illuminate the room. A comfortable sofa and two leather chairs are arranged around a coffee table. Decorative elements include a fireplace and potted plants, creating a welcoming atmosphere.
Apartment in Hampton Bays
4.84 out of 5 average rating, 133 reviews

Vacation at the Beach: Entire Home

EmilyRating, 5 stars8 months ago
We had a great stay! This was our first time in the Hamptons and the space was welcoming, well located to the beach, and a nice place to chill with a beautiful garden. Check in was smooth and all instructions were clear.
Guest favorite
An open studio space features high ceilings and natural light. A modern kitchenette with a small countertop sits adjacent to a dining table with four white chairs. Greenery decorates the walls, and a pendant light hangs from the ceiling, creating a bright atmosphere.
Apartment in Center Moriches
4.85 out of 5 average rating, 78 reviews

Welcome spring in this beautiful quiet studio

BridgetRating, 5 stars1 month ago
Very peaceful spot, responsive host, close to the highway but super quiet.
Top guest favorite
A cozy interior space features white walls and a wooden ceiling with recessed lighting. A guitar leans against a wall, near a stone fireplace. A sofa and a modern wooden coffee table are arranged for relaxation. A spacious bed is positioned in the corner by a window.
Apartment in Hampton Bays
4.97 out of 5 average rating, 104 reviews

Walk to Bay and Ocean-Newly Renovated

JudyRating, 5 stars6 months ago
Lovely, clean, comfortable, well-designed space. Hosts are friendly, responsive, and respectful of guests’ privacy. Would stay again!
A cozy living area features a dark sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, topped with a lantern and fresh flowers. A dining table with wooden chairs is positioned beside a window, allowing natural light to enter the space.
Apartment in Southampton
4.72 out of 5 average rating, 18 reviews

Cozy Hideout

OlaRating, 5 stars8 months ago
Had a great night in this AirBNB. It was just what we needed for a quick stay. The bathroom was great including the shower. The bed was very comfortable. We didn’t make much use of the kitchenette but it had the basics. Some pots and pans would have been helpful or microwaveable cups (I wanted to boil water for tea). The host was communicative and even gave us some recommendations. I’d definitely stay here again!
Superhost
A comfortable bedroom features a spacious bed with neutral bedding and decorative pillows. Two accent chairs are located in one corner, and a wall-mounted TV is visible. Natural light enters through a small window, and textured wall decor adds a touch of elegance.
Apartment in Selden
5 out of 5 average rating, 9 reviews

Home Away From Home

GabryellaRating, 5 stars1 month ago
My sister and I stayed here for a weekend as she was visiting from MA. The place was perfect, with adequate space and clean facilities. The only issue we ran into was the listing describes 2 beds, or at least a futon; however upon staying here we learned there is not one. There is a king bed in the main bedroom, and then narrow couches, one in the bedroom and one downstairs. We had planned on two beds so this was a bit of a surprise. Otherwise, our stay was seamless and we felt very safe and comfortable. The bed was amazing and soft. Hosts were mostly responsive and respectful. A warning for those who use or medicate with cannabis, make sure your car doesn’t smell, as we were parked in front about to go out, one of the hosts insisted we had broken their smoking rules while which definitely was not the case as prior to our stay I had clarified my intent to them to follow all rules and respect their smoking policy. Otherwise, we really enjoyed our weekend and would recommend.

Villa rentals with a fireplace

Top guest favorite
Villa in Southampton
5 out of 5 average rating, 96 reviews

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

IkhelowaRating, 5 stars3 months ago
This place was awesome and the host was extremely gracious.
Top guest favorite
Villa in East Hampton
5 out of 5 average rating, 23 reviews

Luxe| Pool,Jeep w Beach Pass, GameRm, Movie Nights

BrandonRating, 5 stars1 week ago
We absolutely loved our springtime stay! Incredible space inside and outside that enabled our kids ample room to explore and have fun. Ann Marie was extremely responsive and went above and beyond to ensure our stay was memorable!
Superhost
A modern outdoor space features a rectangular pool with crystal clear water, framed by a wooden deck. Comfortable seating arrangements, including two chairs with cushions and a dining table set for six, are complemented by an umbrella for shade.
Villa in North Fork
4.88 out of 5 average rating, 56 reviews

Year-Round Heated Pool Villa - 3 blocks from town

JaimieRating, 5 stars2 weeks ago
George was an excellent Air BnB host!!!! His responses were prompt and answered any questions we had. The location was ideal in Greenport as everything was walking distance. We had an amazing time!
An outdoor space features a well-maintained lawn bordered by a paved pathway. A covered gazebo is visible alongside a pool area, where multiple red chairs are arranged. A garden shed and trees create a serene backdrop for gatherings.
Villa in Medford
4.68 out of 5 average rating, 28 reviews

Oasis Event Venue

ChakraRating, 5 stars3 months ago
It was perfect for the holidays it made everything better for me and my family
Guest favorite
An outdoor living area features comfortable seating with soft cushions, arranged around a coffee table. A spacious pool is visible in the background, surrounded by lounge chairs, with lush greenery providing a serene backdrop.
Villa in Hampton Bays
4.94 out of 5 average rating, 17 reviews

Picturesque 5-bedroom Hamptons villa with pool

MaureenRating, 5 stars7 months ago
Our second year staying at Tony's house! All the comforts of home, with plenty of room for our family. Clean, very comfortable furnishings. Lovely, plentiful linens. The pool area and yard are fantastic! Once again, it was a pleasure to stay there. We hope to go back next year!
Top guest favorite
Villa in Guilford
5 out of 5 average rating, 27 reviews

TREETOPS! An upscale, unique 5 bdrm home with POOL

DoloresRating, 5 stars1 month ago
Very spacious house in charming town. Right next to hiking trails.
Top guest favorite
An open-concept living space displays high ceilings with exposed beams. A modern kitchen features wooden cabinetry and stainless steel appliances. Two stylish cream-colored chairs are positioned on a light wood floor, with large windows allowing natural light to illuminate the room.
Villa in Hampton Bays
5 out of 5 average rating, 16 reviews

Hamptons Bungalow With Pool

LiliRating, 5 stars7 months ago
Wow, this has been one of the most beautiful homes I have stayed at. Straight out of Architectural Digest indeed - Jenna has a true eye for outstanding decor! Jenna is a host to dream of! Thank you we had a beautiful weekend!

Quick stats about vacation rentals with a fireplace in Southold

  • Total rentals

    110 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    1.9K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    40 properties have a pool

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