Shelter Island Heights Vacation Rentals

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Our top choices for Shelter Island Heights vacation rentals

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,293 reviews)
"Nice pool, great restaurant "
United States
April
The price is ¥21,415
¥27,490 total
includes taxes & fees
Feb 16 - Feb 17
Montauk Manor

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is ¥28,749
¥73,797 total
includes taxes & fees
Mar 3 - Mar 4
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is ¥20,358
¥26,620 total
includes taxes & fees
Feb 12 - Feb 13
Windward Shores Ocean Resort

Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is ¥15,296
¥148,992 total
includes taxes & fees
Feb 12 - Feb 13
Blackberry: Private home with jacuzzi year-round

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (35 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is ¥12,376
¥27,807 total
includes taxes & fees
Feb 23 - Feb 24
1-bedroom cottage with Grove Beach 🏖️ access.

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is ¥8,498
¥69,375 total
includes taxes & fees
Feb 12 - Feb 13
Seabreeze #3: Cozy Cottage by the beach

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (15 reviews)
"We enjoyed our stay! We were able to fit a pack and play for our 1 year old in the game room, which was a fun space. The fenced-in back yard was perfect for our dog. "
United States
Christine S.
The price is ¥25,718
¥53,467 total
includes taxes & fees
Feb 16 - Feb 17
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is ¥18,387
¥31,069 total
includes taxes & fees
Feb 24 - Feb 25
American Beech in Greenport - Petite King Room 7

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
9.6 out of 10, Exceptional, (23 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ¥15,296
¥206,538 total
includes taxes & fees
Feb 17 - Feb 18
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
The price is ¥74,010
¥102,211 total
includes taxes & fees
Feb 25 - Feb 26
Offshore Residences

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
United States
Panagiota K.
The price is ¥41,022
¥110,946 total
includes taxes & fees
Feb 12 - Feb 13
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is ¥50,216
¥98,153 total
includes taxes & fees
Feb 12 - Feb 13
Immaculate Waterfront 2 bedroom!

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (9 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is ¥26,282
¥61,413 total
includes taxes & fees
Feb 24 - Feb 25
Beach Cottage, private beach and pass

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is ¥39,350
¥87,596 total
includes taxes & fees
Feb 12 - Feb 13
Renovated Townhouse walk to all

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is ¥38,647
¥86,613 total
includes taxes & fees
Feb 12 - Feb 13
Northfork Townhouse walk to all

Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.2 out of 10, Wonderful, (9 reviews)
"Great location and a nice room!"
United States
Angela M.
The price is ¥14,261
¥33,077 total
includes taxes & fees
Feb 15 - Feb 16
Freeboard at Soundview · Beach+Ocean+Sunrise

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is ¥42,941
¥90,629 total
includes taxes & fees
Feb 18 - Feb 19
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"We loved our stay!"
United States
Deana L.
The price is ¥35,134
¥85,531 total
includes taxes & fees
Feb 13 - Feb 14
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Cottage on Beach front Estate with Dockage .Walk to Village

Cottage on Beach front Estate with Dockage .Walk to Village
Pipes Cove
10.0 out of 10, Exceptional, (75 reviews)
"Wonderful stay at such a special spot. "
United States
Meg B.
The price is ¥46,353
¥59,667 total
includes taxes & fees
Feb 28 - Mar 1
Cottage on Beach front Estate with Dockage .Walk to Village

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (43 reviews)
"Great property, would stay here again."
United States
charles b.
The price is ¥38,608
¥80,080 total
includes taxes & fees
Feb 16 - Feb 17
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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.
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Top Shelter Island Heights Hotel Reviews

Find out more about Shelter Island Heights

Search for holiday rentals in Shelter Island Heights on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island Heights using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Shelter Island Heights?

Yes, you can find vacation rentals close to the most popular attractions in Shelter Island Heights, or you can select a more remote option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the beaches in Shelter Island Heights. Make sure you have time to check out the golf courses and entertainment choices during your trip.

What's the top vacation rental that Shelter Island Heights has to offer?

Gorgeous private Hamptons house with pool and volleyball court: You might want to consider this vacation rental near Shelter Island Heights, which offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a fridge, an oven, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a pool table.

How many vacation rentals are there in Shelter Island Heights?

With 32 Expedia vacation rentals, you're sure to find just the right place for your Shelter Island Heights stay.

What’s there to see and do in Shelter Island Heights?

Sunset Beach and Crescent Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Shelter Island Country Club and Sylvester Manor.

What’s a vacation rental in Shelter Island Heights like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Shelter Island Heights. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.