Photo by Erisa Dilo

Search Vacation Homes in Shelter Island Heights

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 1664 Vacation Homes in Shelter Island Heights with updated reviews, rates, and availability.

Property grounds
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
8.0 out of 10, Very Good, (1)
"The property was perfect for our needs! My husband was able to work from the desk in the primary bedroom during the day while my mom and I shopped and explored nearby! Our dog LOVED the backyard and space to explore. We didn’t even need to go venture to the nearby dog park, but that was also super close! As out of towners, unfamiliar with locale, we would recommend bottled water for drinking. Everywhere we went was 5-15 min drive, we very much enjoyed our stay and grateful for the opportunity to...
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Exterior
Enjoy the North Fork of Long Island at Our Lovely Home
Enjoy the North Fork of Long Island at Our Lovely Home
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (83)
"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"
The price is $950
$1,314 total
includes taxes & fees
May 28 - May 29
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Outdoor pool, a heated pool
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (22)
"Celebrated the holidays with my grown children to be near my dad and brother. The house is lovely. We had a wonderful time. My daughter suggested we come back in the summertime to take advantage of the amenities - beautiful pool and nearby beaches. Highly recommend!!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Fridge, microwave, oven, stovetop
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
10.0 out of 10, Exceptional, (41)
"Very nice place. Would definitely stay there again (actually this our second stay at the property). Clean, well equipped and the pictures are accurate."
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
Property grounds
Waterfront Beach House
9.6 out of 10, Exceptional, (33)
"The cottage is a perfect cozy stay on the water - we stayed in the winter and still were able to enjoy the sand and the sunrises right outside the window. House is well-appointed and well-located within area with access to restaurants and shops in Clinton, Madison, Westbrook, Old Saybrook, etc."
Waterfront Beach House
Property grounds
The SandPiper
9.4 out of 10, Exceptional, (3)
"This listing was exactly as described and was a great little apartment in Greenport with everything we needed. About a 10 minute walk to downtown area which was very convenient. It sits on a busy street so there is some noise from the road but it did not bother us too much and the host provided noise machines in the bedrooms which was very helpful. Overall I recommend this apartment and would definitely stay in the future!"
The SandPiper
Private kitchen | Fridge, microwave, oven, stovetop
Beach Cottage, > .5 walk to beach, quaint, Beach community
10.0 out of 10, Exceptional, (1)
"Pretty gingerbread cottage, well appointed. Lovely area, 2 min walk to the beach. Owners super helpful. Overall beautiful, serene, highly recommmend."
The price is $162
$326 total
includes taxes & fees
May 29 - May 30
Beach Cottage, > .5 walk to beach, quaint, Beach community
Outdoor pool
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (27)
"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Interior
Airstream Art Studio Sculpture/Nature Preserve
10.0 out of 10, Exceptional, (1)
"I found it cozy, comfortable and very peaceful. Bonus wildlife visits of deer, geese and turkeys, Most people will understand this accommodation as quality “clamping”."
The price is $150
$237 total
includes taxes & fees
May 27 - May 28
Airstream Art Studio Sculpture/Nature Preserve
Fridge, microwave, stovetop, dishwasher
Remodeled Farmhouse in Waterford Near 2 Beaches!
10.0 out of 10, Exceptional, (60)
"Great stay, convenient location, very charming house with everything we needed."
Remodeled Farmhouse in Waterford Near 2 Beaches!
1 bedroom, WiFi, bed sheets
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
10.0 out of 10, Exceptional, (33)
"Perfect location!"
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Fridge, microwave, oven, stovetop
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
10.0 out of 10, Exceptional, (21)
"Our group of four friends in our 50s loved our stay here. Heather was a responsive, welcoming, flexible host who left us a card, bottle of wine and a prepped wood pile in the fire pit. The decor was tasteful and beautiful, clean and modern. The mattresses were firm, which we liked. We made use of the comfortable couch on the deck as well as the gas fireplace in the living room. The location is lovely and we had a short, 5-minute walk to the beach. Birders would enjoy the tremendous diversity of...
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
Property grounds
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
10.0 out of 10, Exceptional, (162)
"Got away for a girls weekend and this was perfect. It was close to wineries, and a short Uber away to Greenport. The house was comfortable, clean, and private with enough space for all 8 of us. The outside was also beautiful- right on the water. Highly recommend!!"
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
Pool
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
10.0 out of 10, Exceptional, (10)
"We had a big group with all different ages. Everybody enjoyed their stay. The home was clean, comfortable, and very thoughtfully decorated. The pool table, poker table and Pac-Man kept us all entertained during out time there. Hosts were friendly and responsive."
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
A heated pool
July month or weekly still available. Hampton 5br, pool, hot tub, private beach.
10.0 out of 10, Exceptional, (67)
"The house was great - just as listed and very comfortable / kid friendly. There wasn't a whole lot to do in the area over the holidays but we enjoyed the house, trampoline and jungle gym."
July month or weekly still available. Hampton 5br, pool, hot tub, private beach.
Fridge, microwave, oven, dishwasher
Close to Mystic, Stonington, Westerly. Room for everyone. 3 mins to Ocean Beach.
9.8 out of 10, Exceptional, (20)
"Nice quiet neighborhood. Plenty of bedrooms, really great comfy beds, & 3 bathrooms! WONDERFUL!!! Large dining room table where you all can gather for meals. The very best guide book of how the house works, places to eat & general information that was so nice to know, not being from around there. Welcome snacks, a very nice touch! Would HIGHLY recommend to anyone looking to visit UConn, the navel academy or the Mystic Seaport area."
Close to Mystic, Stonington, Westerly. Room for everyone. 3 mins to Ocean Beach.
Don't see what you're looking for?
See all available properties in Shelter Island Heights
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Shelter Island Heights

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1021)
"Best affordable hotel in Montauk"
The price is $151
$192 total
includes taxes & fees
May 28 - May 29
Montauk Manor
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (296)
"We enjoyed our stay!"
The price is $169
$203 total
includes taxes & fees
Jun 12 - Jun 13
Montauk Oceanside Suites
On the beach, white sand
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (220)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is $161
$238 total
includes taxes & fees
May 28 - May 29
The Surf Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Shelter Island Heights Vacation Homes information

Number of reviews
554
Accommodation
1664 Vacation Homes
Lowest Price
$150
Highest Price
$950

Recent reviews of Shelter Island Heights hotels
Expedia verified reviews

The Niantic Inn

The Niantic Inn

5/5 Excellent
Excellent hotel!
"Our experience in Niantic and at the Niantic Inn was great! The owner was very friendly and helpful. There was EVERYTHING you could need provided in the clean and comfortable room, with many extras such as bottles of water and snacks. The location of the hotel was better than we imagined as the owner told us about a lovely and scenic 1 mile walk along the boardwalk along the bay, which started right across the street from the Niantic Inn! . She gave suggestions for coffee shops and anything else we asked about. Personal and professional. A delightful stay! Thank you’ "
A verified traveler stayed at The Niantic Inn
Posted 1 day ago
The Niantic Inn