
Vacation rentals with a fireplace in Shelter Island
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Top-rated accommodations with a fireplace in Shelter Island
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Popular amenities for Shelter Island accommodations with a fireplace
House rentals with a fireplace

Cozy Springs Getaway
This house is in a quiet safe neighborhood, 30 mins from Montauk Beach and half the cost for 5 guests. Overall we loved it! The host recommended restaurants which is helpful. When we-reported a problem, someone was there to fix it the next morning. Kitchen well stocked, plenty of outdoor seating, comfy couches. Strange full bathroom cotton curtains a bit long and no liner, difficult to dry. The bath off the master bedroom the floor floods because curtain in there is lined but a bit short. Gotta keep a towel down. Garage is wonderful, laundry in basement handy. Decks off bedroom and patio off dining room both lovely. are beautiful lovely place to stay.

Hamptons Retreat | Pool, Volleyball, Jacuzzi
Aida’s house is very nice place to stay for a getaway in the Hamptons. Amazing outdoor area. Great for traveling with kids. Aida is a great host!

Welcome To Piper's Rest
It was wonderful stay and I’d go back anytime

Boulder Lake House Retreat
This lake house was absolutely beautiful! Brought my girls there as a little get away in preparation for my wedding day. Jhismery was responsive so quickly and so accommodating with some questions I had. Stunning view of the lake and the house had this homey feel to it. I would book it again as a weekend getaway again!

Peaceful Guesthouse
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!

Hampton Bays Hideaway!
We had another great stay at Claudia's place! This was our third visit to this location, and likely not our last. Thank you!!

Charming Home in WestHampton Beach
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.

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.
Apartment rentals with a fireplace

Lyon's den by Wooster Square!
We enjoyed our stay at Dariel’s very much. Convenient location for our needs. Everything was spotless and had everything we needed for our stay. Would definitely choose this location again and recommend to others!

Sugarloaf Annex
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!

Wooster SQ | Downtown Yale |Skyline Deck | Laundry
Great location. Right next to cherry blossoms and the famous pizza spots. Comfy beds

The Professors Flat
The location and comfort can’t be beat. We stayed at the professor’s flat for a full semester while I was teaching at Yale and it was perfect for a couple and a cat. We even had a couple of friends visit and stay over comfortably during that time. We truly lived in the place like it was our home, because it felt like it: it was cozy, and despite a smaller kitchen than we’re used to, it was well equipped, and we were able to cook a lot and even host dinner parties. It’s very conveniently located to everything in New Haven/the East Rock neighborhood & we walked everywhere. Also very convenient to the freeway. A parking spot was included in our rent as well. Remy, Hilary and Sal were always responsive and ready to take care of anything that needed attention. Remy also gave us and all the tenants extras like baked goods, and samples of her great Italian cooking on occasion (around the holidays). They also gave us fire logs for the fireplace we used our entire last month in town.

Whaling Captain Pierson's Cottage
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.

Elegant Apartment
This is my 3rd stay here. I sometimes come on my own to visit my daughter at Yamaha and I pay extra per night to stay at this comfy relaxing spot so I feel at home. I have private parking, easy entry, close to downtown Yale shopping and minutes from raved Whooster Villlage. Don’t be hesitate because it is on the corner of the busy street, it allows for spreading out of family and each bedroom with own bathroom/TV sitting area. The upstairs room can get warm but use the AC unit in room and it is cool in no time! This will be my home away from home for my daughter’s next 3 years at UNH. My only suggestion is the main floor bedroom does not have King size bed but the room Itself is gorgeous! Enjoy and highly recommend this spot!

Walk to Bay and Ocean-Newly Renovated
Lovely, clean, comfortable, well-designed space. Hosts are friendly, responsive, and respectful of guests’ privacy. Would stay again!

King 1BR W/ Parking, Pool & Gym
Great place! Extremely spacious and exceptionally clean. Also very quiet. Free parking was a plus, with a huge fitness center. Communication was also excellent. I’ll definitely stay here again.
Villa rentals with a fireplace

Year-Round Heated Pool Villa - 3 blocks from town
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!

Oasis Event Venue
It was perfect for the holidays it made everything better for me and my family

Luxury| Pool| GOLF Sim| HotTub| MovieTheater| Arcade
We had a lovely stay this April. House was spotless and newly refurbished. Pool area great (early in season so braved a cold plunge!!!) and appreciated the separate hot tub too. Pool furniture all brand new and special mention of the best kitted out games room I have ever seen! Location great. Very quiet but short car ride to East Hampton proper. Sammi’s beach a 10 min walk away. A fantastic stay and would not hesitate to recommend to others.

TREETOPS! An upscale, unique 5 bdrm home with POOL
Very spacious house in charming town. Right next to hiking trails.

Hamptons Bungalow With Pool
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 Shelter Island
Total rentals
80 properties
Nightly prices starting at
$207 CAD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Jennings Beach
- Walnut Public Beach
- Seaside Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Shennecossett Beach
- Sunken Meadow State Park
- Connetquot River State Park Preserve
- Outer Beach at Smith Point County Park
- Long Island Aquarium
- Groton Long Point Main Beach
- Attawan Beach
- East Beach