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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.
$205 nightly
The price is $234
Nov 30 - Dec 1
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.
$196 nightly
The price is $223
Nov 15 - Nov 16
Total with taxes and fees
4. Aqua Vista
Aqua VistaPipes Cove
10.0 out of 10, Exceptional, (53 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
Carey D.
$212 nightly
The price is $242
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.
$305 nightly
The price is $348
Nov 12 - Nov 13
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.
$375 nightly
The price is $428
Nov 12 - Nov 13
Total with taxes and fees
7. North Fork Resort
North Fork ResortGreenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
Altynai
$321 nightly
The price is $367
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.
$254 nightly
The price is $290
Nov 12 - Nov 13
Total with taxes and fees
9. Montauk Manor
Montauk ManorMontauk
9.2 out of 10, Wonderful, (1,424 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.
$493 nightly
The price is $563
Dec 1 - Dec 2
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.
$469 nightly
The price is $535
Nov 12 - Nov 13
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
$170 nightly
The price is $194
Nov 12 - Nov 13
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.
$414 nightly
The price is $473
Nov 12 - Nov 13
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.
$712 nightly
The price is $813
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
$287 nightly
The price is $328
Nov 16 - Nov 17
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 25 - Nov 26
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.
$793 nightly
The price is $906
Dec 1 - Dec 2
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.
$435 nightly
The price is $497
Nov 12 - Nov 13
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.
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
$429 nightly
The price is $454
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.
Find vacation rentals that suit your style
Apartments
Aparthotels
Top Shelter Island Heights Hotel Reviews
Silver Sands Motel & Beach Bungalows
Silver Sands Motel & Beach BungalowsGreenport
10/10 Excellent
We had a lovely stay.
Nicole
