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

Private beach, fully updated house, on 2 acres.
Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

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".)

Spacious Oceanfront Getaway with Spectacular Views
Perfect vacation getaway! Awaken to the sun rising over Long Island Sound! Panoramic waterfront views from 70 ft of windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, fish, read a book, or watch the sailboats go by! (Not suitable for children/pets/events.)

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!

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.

Beautiful beach home with pool & water views!
Perfectly situated just past the Island Boatyard and Salt in a blissful neighborhood surrounded by water on 3 sides. 4 town landings and beach access right across the street. Newly renovated gourmet kitchen with large island and beautiful quartz counters. Back deck offers full outdoor dining space with propane Weber grill, wicker seating area with beautiful propane Firepit for hours of evening enjoyment and chaise lounges by the pool.

Elegant Modern Artist's Residence
This simple and serene home is set against a farm preserve, exposed to beautiful light and views and biking distance to the beach. Very relaxing - a terrific, creative space for a couple or small group. We are a pet friendly home so if allergic please be aware. A large vegetable garden is maintained on the property and is available for guests to harvest as they like. Fresh salad greens, herbs, vegetables for you to enjoy!
Popular amenities for Shelter Island fireplace rentals
House rentals with a fireplace

Private & Pristine with Pool and Kid’s Playard

1800 Historical EH Home, 1 Mile to Town!

Renovated Southampton Home+Pool

Cottage by the beach

5BR/3BA: Shelter Island, Waterview, Close to beach

Designer home in Sag Harbor : 5BR walk to beach

Luxury by the Sea!!

Chic greenport village home
Apartment rentals with a fireplace

Lovely Loft Apartment with Private Beach Access!!

Sugarloaf Annex

Hamptons Waterfront Suite | Private Hot Tub

A 1 BR Luxury Apt to relax w/hot tube

Hamptons The Vineyard Studio

Vacation at the Beach: Entire Home

Greenport Condo with Stunning Views & Beach Access

Cozy Studio 15 Min From Hampton Beaches
Other vacation rentals with a fireplace

Charming Scandinavian Inspired Beach Cottage

Sag Harbor Hamptons hideaway

Stylish Montauk Village Escape for Any Season

The Melody Too

East Hampton Rental w/ Pool, Moments to Amenities

Peaceful cottage

Steps to Train, Dining & Beach US Open Golf

The Olde Church in Greenport
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.ﺇ2,391 | ﺩ.ﺇ1,443 | ﺩ.ﺇ2,156 | ﺩ.ﺇ2,204 | ﺩ.ﺇ2,618 | ﺩ.ﺇ2,754 | ﺩ.ﺇ3,030 | ﺩ.ﺇ2,938 | ﺩ.ﺇ2,648 | ﺩ.ﺇ2,204 | ﺩ.ﺇ2,376 | ﺩ.ﺇ2,251 |
| 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.ﺇ551 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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Rentals with a fire pit Shelter Island
- Family-friendly rentals Shelter Island
- Rentals with pools Shelter Island
- Rentals with a hot tub Shelter Island
- Rentals with a washer and dryer Shelter Island
- House rentals Shelter Island
- Pet-friendly rentals Shelter Island
- Rentals with beach access Shelter Island
- Waterfront rentals Shelter Island
- Rentals with outdoor seating Shelter Island
- Rentals with a patio Shelter Island
- Rentals with a kayak Shelter Island
- Beachfront rentals Shelter Island
- Fitness-friendly rentals Shelter Island
- Rentals with a fireplace Suffolk County
- Rentals with a fireplace New York
- 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





