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

Whaling Captain Pierson's Cottage
Whaling Captain Pierson's Cottage is at a waterfront property. A unique environmental experience, nestled in nature but only a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only cottage offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets and a private low-tide beach. (See my reviews from my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Apartment TOO".)

Serenity + privacy; 1 block to waterfront dining
Enjoy the space and privacy of your own home! Located near all of the best Hampton's attractions. Enjoy your large home surrounded by nature and serenity. Swim in your pool, spark up the BBQ + firepit, enjoy al fresco dining under the stars. Stream on your 80' TV + cook in your fully stocked Chef's kitchen. Stroll just 1 block to the best waterfront dining + cafe for drinks/dinner/morning coffee on the sea. You will be 8 mins to Main St., 10 mins to beaches, close to museums, coffee + more!

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!

Private & Pristine with Pool and Kid’s Playard
INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

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!

Artists Sag Harbor Village Retreat
This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Fully self contained and private. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking in driveway close to entrance. Not suitable for infants or children.

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.

Hay Beach Family Home: Fire Pit, Playroom, Yard
Two blocks from Hay Beach, this family-and-dog-friendly 3BR sleeps 6 in a quiet Shelter Island neighborhood. Fenced yard, fire pit, playroom, crib, toddler toys, beach gear, and bikes included. The home was built for families: open living area with wood-burning fireplace, full kitchen, 2 full baths, basement playroom, and workout space. Outside: fully fenced yard, fire pit, sun loungers, propane grill, Big Green Egg. Winter stays: $0 cleaning fee Nov–Mar.

Modern Farmhouse Steps to Beach & Love Lane
Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

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.

Renovated Townhouse, Walk to All
Discover the North Fork from our stylishly renovated 100-year-old townhouse! Perfectly located, you can walk to town, beaches, and a local brewery. This bright, airy home features a new kitchen, central AC, and a private patio with a grill. Comfortably sleeping up to 8 guests, it's the ideal base for families or groups exploring Long Island's wine country. Park your car and enjoy a walkable getaway!

Cozy Cottage on the Great Pond near beach.
In the heart of wine country is the adorable , nautical inspired cottage surrounded by nature, on a beautiful freshwater pond, a quick walk or bike ride away from a beautiful beach on Long Island Sound. Hiking, fishing, wine tours, farmstands abound!
Popular amenities for Shelter Island fireplace rentals
House rentals with a fireplace

Private beach, fully updated house, on 2 acres.

Silver House: 3BR Home with Private Beach Access

Luxe Southampton Home w/Pool 5 Min Walk to US Open

Cottage by the beach

Designer home in Sag Harbor : 5BR walk to beach

Scandinavian Cottage

Family Retreat with Heated Pool, Hot Tub, Sauna.

Montauk Private Beach Bungalow
Apartment rentals with a fireplace

Lovely Loft Apartment with Private Beach Access!!

Medford Seclusive Getaway

Vacation at the Beach: Entire Home

Greenport Condo with Stunning Views & Beach Access

Stedley Creek

Cozy Studio 15 Min From Hampton Beaches

Rustic Log Cabin, Long Island Vineyards

Walk to Bay and Ocean-Newly Renovated
Villa rentals with a fireplace

Year-Round Heated Pool Villa - 3 blocks from town

Just renovated Southampton retreat w/ heated pool

Southampton Private Retreat with Ocean Views

Hamptons Retreat | Pool, Hot Tub, Sleeps 10

TREETOPS! An upscale, unique 5 bdrm home with POOL

11 Min from Shinnecock Hamptons Bungalow with Pool
When is the best time to visit Shelter Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 2,391 | ﺩ.ﺇ 1,443 | ﺩ.ﺇ 2,156 | ﺩ.ﺇ 2,204 | ﺩ.ﺇ 2,618 | ﺩ.ﺇ 2,754 | ﺩ.ﺇ 3,030 | ﺩ.ﺇ 2,938 | ﺩ.ﺇ 2,648 | ﺩ.ﺇ 2,204 | ﺩ.ﺇ 2,376 | ﺩ.ﺇ 2,251 |
| 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 vacation rentals with a fireplace in Shelter Island

Total vacation rentals
Explore 80 vacation rentals in Shelter Island

Nightly prices starting at
Shelter Island vacation rentals start at ﺩ.ﺇ 551 per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Shelter Island vacation rentals include wi-fi access

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

4.9 Average rating
Shelter Island stays are highly rated by guests—averaging 4.9 out of 5!
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- Family-friendly rentals Shelter Island
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- Rentals with outdoor seating Shelter Island
- Rentals with a patio Shelter Island
- Rentals with a fireplace Suffolk County
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- Rentals with a fireplace United States
- Beach
- Yale University
- Cooper's Beach, Southampton
- Fairfield Beach
- Charlestown Beach
- East Matunuck State Beach
- Mohegan Sun
- Ocean Beach Park
- Foxwoods Resort Casino
- Mystic Seaport Museum
- Sunken Meadow State Park
- Point Judith Lighthouse
- Hammonasset Beach State Park
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Long Island Aquarium
- Blue Shutters Beach
- Wölffer Estate Vineyard
- Mount Southington Ski Area
- Orient Beach State Park
- Ocean Beach
- Meschutt Beach
- Mystic Aquarium





