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Villas in Shelter Island Heights

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Dec 12 - Dec 14
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Villas in Shelter Island Heights

No exact matches found, but these alternatives could be just right

Recommended hotels in Shelter Island Heights

Exterior
House on Chase Creek

Guesthouse in The Heights

2.5 star property
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
$185 nightly
The price is $211
Dec 8 - Dec 9
Total with taxes and fees
House on Chase Creek
Exterior
The Rams Head Inn

Inn in Shelter Island Heights

4.0 star property
7.6 out of 10, Good, (18)
"Beautiful views and lovely service "
United States
Lana
$395 nightly
The price is $451
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Rams Head Inn
Outdoor pool, sun loungers
Daunt's Albatross Motel

Motel in Downtown Montauk

2.0 star property
9.0 out of 10, Wonderful, (287)
"The staff is the best, made my birthday stay extra special. Love the room and how clean and cute it was. Best hotel in town."
United States
Tiffany
$168 nightly
The price is $192
Dec 18 - Dec 19
Total with taxes and fees
Daunt's Albatross Motel
One Bedroom Condo King with Steam Shower | Terrace/patio
Offshore Residences

Condo in Downtown Montauk

4.5 star property
$579 nightly
The price is $662
Dec 7 - Dec 8
Total with taxes and fees
Offshore Residences
Ocean View 2 Queens | Premium bedding, pillowtop beds, blackout drapes, free WiFi
Offshore Montauk

Offshore Montauk

2.0 star property
9.2 out of 10, Wonderful, (74)
"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"
United States
Erica
$131 nightly
The price is $150
Jan 4 - Jan 5, 2026
Total with taxes and fees
Offshore Montauk
Hero King Patio Deluxe | Terrace/patio
Hero Beach Club

Motel in Montauk

4.0 star property
9.0 out of 10, Wonderful, (201)
"Great weekend trip "
United States
Timothy
$245 nightly
The price is $280
Dec 28 - Dec 29
Total with taxes and fees
Hero Beach Club
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn

Motel in Culloden Shores

2.0 star property
8.4 out of 10, Very Good, (878)
"Really clean and nice location"
United States
Tiara
$120 nightly
The price is $138
Jan 4 - Jan 5, 2026
Total with taxes and fees
Kenny's Tipperary Inn
Front of property - evening/night
Montauk Manor

Aparthotel in Montauk

3.5 star property
9.2 out of 10, Wonderful, (1265)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
$156 nightly
The price is $178
Dec 18 - Dec 19
Total with taxes and fees
Montauk Manor
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa

Resort in Montauk

4.0 star property
8.2 out of 10, Very Good, (695)
"Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities"
United States
Alex
$472 nightly
The price is $540
Dec 8 - Dec 9
Total with taxes and fees
Gurney's Montauk Resort & Seawater Spa
Frette Italian sheets, premium bedding, down comforters
The Roundtree, Amagansett

The Roundtree, Amagansett

4.5 star property
10.0 out of 10, Exceptional, (91)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
$624 nightly
The price is $713
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Roundtree, Amagansett
Exterior
Journey East Hampton

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (159)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
$207 nightly
The price is $237
Dec 8 - Dec 9
Total with taxes and fees
Journey East Hampton
Property grounds
Mill House Inn

Bed & Breakfast in Pantigo Road Historic District

5.0 star property
9.0 out of 10, Wonderful, (73)
"We stayed at the Inn for our anniversary last weekend. We are devotees of bed and breakfast hotels and loved this one. We arrived to find a huge, and I mean, huge, bouquet of the most beautiful white roses waiting for us in the suite that they upgraded us to. Totally unexpected. These folks could not do enough for us. Breakfast was extremely nice, cooked to order with quality ingredients. Bed was extremely warm and comfortable. The management, the staff, can't say anything negative about...
United States
margaret
$330 nightly
The price is $377
Dec 7 - Dec 8
Total with taxes and fees
Mill House Inn
Aerial view
East Hampton Art House Bed & Breakfast

Bed & Breakfast in Clearwater Beach

4.0 star property
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
$437 nightly
The price is $499
Dec 8 - Dec 9
Total with taxes and fees
East Hampton Art House Bed & Breakfast
Exterior detail
The Huntting Inn

Bed & Breakfast in Egypt Lane Historic District

3.5 star property
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
$393 nightly
The price is $447
Dec 17 - Dec 18
Total with taxes and fees
The Huntting Inn
Garden
The 1770 House Restaurant & Inn

Inn in East Hampton

4.0 star property
9.8 out of 10, Exceptional, (160)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
$279 nightly
The price is $363
Dec 8 - Dec 9
Total with taxes and fees
The 1770 House Restaurant & Inn
Garden
The Maidstone

The Maidstone

4.0 star property
8.0 out of 10, Very Good, (150)
"We had a wonderful stay "
United States
Sabrina
$260 nightly
The price is $298
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Maidstone
Exterior
Wainscott Woods Retreat

Wainscott Woods Retreat

2.5 star property
7.0 out of 10, Good, (9)
"Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area."
United States
Ivan
$299 nightly
The price is $342
Dec 7 - Dec 8
Total with taxes and fees
Wainscott Woods Retreat
Front of property
The Sagaponack

Bed & Breakfast in Wainscott

3.0 star property
8.8 out of 10, Excellent, (210)
"Clean & amenities, staff friendly Thank you "
United States
Archil
$178 nightly
The price is $204
Dec 15 - Dec 16
Total with taxes and fees
The Sagaponack
Terrace/patio
Inn at Harbor Hill Marina

Bed & Breakfast in Niantic

3.5 star property
9.4 out of 10, Exceptional, (1002)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
$159 nightly
The price is $183
Dec 7 - Dec 8
Total with taxes and fees
Inn at Harbor Hill Marina
Front of property
Topping Rose House

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (136)
"Great rooms, staff and food"
United Kingdom
Alexandra
$553 nightly
The price is $636
Dec 16 - Dec 17
Total with taxes and fees
Topping Rose House
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

Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

10/10 Excellent
"We stayed for three nights and no issues at all. Place is well taken care. "
Dominick 3-night trip
Posted 2 days ago
Sleep Inn & Suites Niantic North

Find out more about Shelter Island Heights

Shelter Island Heights Villas information

Number of reviews
5,108
Accommodation
41 Villas
Lowest Price
$138
Highest Price
$713

Frequently asked questions

How much do villas in Shelter Island Heights cost?
Villas in Shelter Island Heights range between $138 and $713 per night. These stays provide the privacy of your own space at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Shelter Island Heights?
Expedia guests love staying at Villa Lavender. Base yourself at this 3.5-star property which comes with a terrace and a garden. Villa Machis is another sought-after option worth shortlisting. Spend your break at this 3.5-star stay and you'll have access to amenities such as a garden and a terrace. There are multiple villas in Shelter Island Heights with a total average guest review rating of 8.8.
How many villas are there in Shelter Island Heights?
Shelter Island Heights has 41 villas to choose from. Find your perfect stay quickly and easily by clicking the "Villa" checkbox under the "Property type" tab in our filter tool.
Are there any family-friendly villas in Shelter Island Heights?
A lot of visitors in search of a family-friendly villa in Shelter Island Heights pick Villa Lavender. With a 3.5-star rating and useful amenities like a barbecue grill and WiFi, it'll get your crew's seal of approval. Villa Machis is a 3.5-star stay that's also well-frequented by vacationing families. A nearby zoo and WiFi help make it an awesome base for your Shelter Island Heights getaway. Shelter Island Heights has no shortage of family-friendly attractions to check out that'll keep the kids entertained. 67 Steps Beach and Orient Beach State Park promise fun for travelers of all ages.
Why book your villa in Shelter Island Heights with Expedia?
Reserving a villa in Shelter Island Heights is as simple as deciding on your travel dates and choosing the option that checks your boxes. Searching for something inexpensive or upscale, or a stay that also offers a kitchen and laundry? Use Expedia's search filters to narrow your results and find your ideal pad.
How can I find cheap villas in Shelter Island Heights?
An excellent way to track down cheap villas in Shelter Island Heights is with Expedia's convenient filter tool. Narrow down your search by star rating, amenities and budget to land awesome deals in only a couple of clicks.
What is there to do near my villa in Shelter Island Heights?
After you've settled into your villa, set out and discover the incredible things Shelter Island Heights has for you to experience. Sylvester Manor is a top attraction to add to your must-do list.

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