
Holiday rentals with a fireplace in Southold
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Top-rated rentals with a fireplace in Southold
Guests agree: these rentals with a fireplace are highly rated for location, cleanliness and more.

Modern Southampton Cottage | Heated Pool & Peloton
Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

Cozy Farmhouse Retreat in North Fork, NY
A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

Silver House: 3BR Home with Private Beach Access
Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Summer Retreat at the beach , enjoy Wine Country
* We provide a Beach Parking Pass for all Southold Town Beaches * 10 min walk to neighborhood sandy beach! * 5 min walk to vineyard with tasting room. Spacious Contemporary home. Master Bedroom plus 2 more bedrooms and 2 bathrooms on the second floor. Living room & kitchen on main floor. Wake up to beautiful garden view. Large kitchen and dining area for the whole family. Just minutes from Long Island's wineries and wedding venues. This home comes complete with everything you need!

Charming Southampton Light filled Cottage
Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

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 with modern updates. 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.

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.

Northfork Townhouse-walk to all/Newly Renovated
Fully Renovated Townhouse walking distance to town, beaches, parks, brewery and short bike to wineries. Brand new Kitchen, bathrooms & bedrooms. Enjoy all the North Fork has to offer: wineries, breweries, amazing restaurants, shops and beaches! 3 Bedrooms 1.5 bathrooms. We welcome you to come stay in our beautiful home and take in all the beauty of the North Fork. You can park your car and not have to drive again till you leave!

Greenport Beach house Mini Resort Spa & Catering
Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Exclusive Sag Harbor Compound
A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

Beautiful condo on Long Islands Northfork
This condo is beautifully decorated and has a wonderful stone fire place. Gorgeous shiplap walls with Navy accents. There is also a new deck and wonderful dinning set outside. This unit has capabilities to be handicap accessible. Both bedroom have private bathrooms. The living room sectional opens up to a full sleeper making this condo able to sleep six people. All rooms have flat screen smart tv's.
Popular amenities for rentals with a fireplace in Southold
House rentals with a fireplace

Mastic Beach Surf House

Spectacular Southampton Retreat!

Historic East Hampton Home - Private Beach Access

Private beach, fully updated house, on 2 acres.

Hamptons - Shelter Island Farmhouse

Breezy Waterfront Home With private Dock

1800 Historical EH Home, 1 Mile to Town!

Secluded Luxury: New Gunite Pool, Walk to Bay
Apartment rentals with a fireplace

Get Salty Abode

Hamptons Waterfront Escape/ Hot Tub/ Resort Style

Sugarloaf Annex

The Vineyard Studio of the Hamptons.

Whaling Captain Pierson's Cottage

Vacation at the Beach: Entire Home

Quiet and comfy studio near the Hamptons

Greenport Condo with Stunning Views & Beach Access
Villa rentals with a fireplace

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

Luxe| Pool|Game Room |Outdoor Movie|HotTub|Firepit

Year-Round Heated Pool Villa - 3 blocks from town

Just renovated Southampton retreat w/ heated pool

Southampton Private Retreat with Ocean Views

Hamptons Bungalow With Pool
When is the best time to visit Southold?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $720 SGD | $703 SGD | $686 SGD | $748 SGD | $720 SGD | $798 SGD | $874 SGD | $886 SGD | $755 SGD | $720 SGD | $720 SGD | $779 SGD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Quick stats about holiday rentals with a fireplace in Southold

Total holiday rentals
Explore 120 holiday rentals in Southold

Nightly prices starting at
Southold holiday rentals start at $117 SGD per night before taxes and fees

Verified guest reviews
Over 2,090 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
120 of Southold holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Southold rentals

4.9 Average rating
Southold stays are highly rated by guests – averaging 4.9 out of 5!
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