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Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Shelter Island Heights vacation rentals
1. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
William
$289 nightly
The price is $330
Nov 26 - Nov 27
Total with taxes and fees
2. The SandPiper
The SandPiperPipes Cove
9.6 out of 10, Exceptional, (58 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
Manuela C.
$197 nightly
The price is $225
Nov 10 - Nov 11
Total with taxes and fees
3. Harbor Heights
Harbor HeightsPipes Cove
10.0 out of 10, Exceptional, (29 reviews)
"Perfect spot to stay on the North Fork!"
Steven R.
$197 nightly
The price is $225
Nov 15 - Nov 16
Total with taxes and fees
4. Aqua Vista
Aqua VistaPipes Cove
10.0 out of 10, Exceptional, (53 reviews)
"Great location and nice spot."
Kerri L.
$206 nightly
The price is $235
Nov 18 - Nov 19
Total with taxes and fees
5. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + OfficePipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
Callie E.
$297 nightly
The price is $339
Nov 10 - Nov 11
Total with taxes and fees
6. Beach Block Hideaway
Beach Block HideawayPipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
Teresa C.
$365 nightly
The price is $417
Nov 11 - Nov 12
Total with taxes and fees
7. North Fork Resort
North Fork ResortGreenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
Altynai
$299 nightly
The price is $341
Nov 15 - Nov 16
Total with taxes and fees
8. American Beech in Greenport - Petite King Room 7
American Beech in Greenport - Petite King Room 7Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
Paul F.
$247 nightly
The price is $282
Nov 10 - Nov 11
Total with taxes and fees
9. Montauk Manor
Montauk ManorMontauk
9.2 out of 10, Wonderful, (1,422 reviews)
"We’ve been to Montauk Manor many times. The inside pool area is updated and nice to use. Gavin a restaurant there is quite convenient. The units are comfortable and lovely with fully stocked kitchens."
barbara
$156 nightly
The price is $178
Nov 30 - Dec 1
Total with taxes and fees
10. Northfork Townhouse walk to all
Northfork Townhouse walk to allGreenport
9.4 out of 10, Exceptional, (9 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"
Beth R.
$506 nightly
The price is $578
Nov 10 - Nov 11
Total with taxes and fees
11. Renovated Townhouse walk to all
Renovated Townhouse walk to allGreenport
9.6 out of 10, Exceptional, (15 reviews)
"The place was as advertised and in great walking distance to everything in town! "
Liz H.
$450 nightly
The price is $514
Nov 10 - Nov 11
Total with taxes and fees
12. Windward Shores Ocean Resort
Windward Shores Ocean ResortNapeague
8.8 out of 10, Excellent, (333 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
Banessa
$167 nightly
The price is $190
Nov 23 - Nov 24
Total with taxes and fees
13. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.Southold
9.6 out of 10, Exceptional, (10 reviews)
"Overall we had a great stay, we weren’t in the apartment much and really only needed it for a place to stay at night. The space is the basement of a home with little natural sunlight. Overall it was ok for a weekend stay."
Kelly V.
$403 nightly
The price is $460
Nov 10 - Nov 11
Total with taxes and fees
14. 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 TownGreenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
Jeannette M.
$723 nightly
The price is $826
Dec 1 - Dec 2
Total with taxes and fees
15. American Beech in Greenport - Deluxe King 6
American Beech in Greenport - Deluxe King 6Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
Jeffrey
$279 nightly
The price is $319
Nov 10 - Nov 11
Total with taxes and fees
16. Montauk Oceanside Suites
Montauk Oceanside SuitesDowntown Montauk
8.4 out of 10, Very good, (461 reviews)
"The room was very clean and well taken care of."
Mitchell
$146 nightly
The price is $166
Nov 23 - Nov 24
Total with taxes and fees
17. Beachfront Greenport Villa
Beachfront Greenport VillaGreenport
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home, great views and host!"
Kate R.
$770 nightly
The price is $879
Nov 10 - Nov 11
Total with taxes and fees
18. Lovely studio with AC in charming Sag Harbor
Lovely studio with AC in charming Sag HarborSag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
Emily t.
$423 nightly
The price is $483
Nov 10 - Nov 11
Total with taxes and fees
19. Year round Jacuzzi - Blackberry East Hampton Home
Year round Jacuzzi - Blackberry East Hampton HomeEast Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
Suzanne R.
$1,275 nightly
The price is $1,342
Nov 10 - Nov 11
Total with taxes and fees
20. Steps to the beach | Seabreeze Cottage #3
Steps to the beach | Seabreeze Cottage #3Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils.
The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off.
The last straw was the huge spider that jumped down from the closet onto me.
We ended up leaving after less than 24 hours and...
Lydia
$417 nightly
The price is $440
Nov 15 - Nov 16
Total with taxes and fees
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
The Chequit
The ChequitThe Heights
10/10 Excellent
We went for a nice weekend getaway and we were not disappointed. The room was really nice, the coffee shop was perfect for a morning latte and cup of coffee. We went to the bar and restaurant both days and the staff were absolutely amazing and professional and provided quality service. The food and drinks were amazing. We wanted peace and tranquility and that’s exactly what we got.
Joseph
