Holiday rentals in Shelter Island Heights

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Top-rated holiday rentals in Shelter Island Heights

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest house in Shelter Island
Lovely Island Cottage
Kick back and relax in this serene, stylish, sparkling adorable cottage. Large, airy living room with vaulted ceiling, fan, AC and full open kitchen. Cozy bedroom with queen size bed and luscious European linens. Spacious, bright bathroom with roomy stall shower. Newly painted with charming wicker furniture and cafe bistro table, Apple TV, Sonos and wifi. Enjoy the peace and beauty of Shelter Island living. Long time residents, we are happy to share all the ins and outs of the island.
16–23 NovIndividual Host,
€ 405 per night
4.95 out of 5 average rating, 22 reviews
Guest favourite
Apartment in Greenport
Beachside Waterview 2Br Condo w/ Pool in Greenport
Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat
22–29 MarIndividual Host,
€ 227 per night
4.91 out of 5 average rating, 107 reviews
Guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars. It is a week minimum during the peak season ( memorial day weekend until labor day weekend)
8–15 JulIndividual Host,
€ 416 per night
4.95 out of 5 average rating, 122 reviews

Popular amenities for Shelter Island Heights holiday rentals

Stay near Shelter Island Heights's top sights

American Beech52 locals recommend
Lucharitos51 locals recommend
Claudio's39 locals recommend
Claudio's Waterfront44 locals recommend
SALT Waterfront Bar & Grill34 locals recommend
Mashomack Preserve70 locals recommend

Other great holiday rentals in Shelter Island Heights

Guest favourite
Home in Greenport
Lovely 1st floor of farmhouse, wineries/downtown
29 Apr – 6 MayIndividual Host,
€ 281 per night
4.9 out of 5 average rating, 29 reviews
Guest favourite
Home in Greenport
Designer's Dream - Charming Boathouse
3–10 JanIndividual Host,
€ 415 per night
4.98 out of 5 average rating, 85 reviews
Guest favourite
Guest suite in Greenport
Private Suite in Greenport Historical District
22–29 JunIndividual Host,
€ 303 per night
5.0 out of 5 average rating, 45 reviews
Guest favourite
Cottage in Shelter Island
Waterfront Getaway on Shelter Island
14–21 NovIndividual Host,
€ 687 per night
4.88 out of 5 average rating, 16 reviews
Guest favourite
Home in Greenport
Walk to Beach or to Town …
13–20 OctIndividual Host,
€ 392 per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Greenport
North Fork Escape - Walk To Village, Beach, Parks
24 Feb – 3 MarIndividual Host,
€ 548 per night
4.9 out of 5 average rating, 84 reviews
Guest favourite
Home in Greenport
Beach House in L.I. Wine Country
24 Sep – 1 OctIndividual Host,
€ 541 per night
5.0 out of 5 average rating, 68 reviews
Guest favourite
Home in Greenport
Historic Stunner in Heart of Village
17–24 FebIndividual Host,
€ 534 per night
5.0 out of 5 average rating, 29 reviews
Guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
9–16 JunProfessional Host,
€ 695 per night
4.96 out of 5 average rating, 90 reviews
Guest favourite
Home in Shelter Island
Spacious house with pool.
30 Jul – 6 AugIndividual Host,
€ 895 per night
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Shelter Island
Modern, spacious SI home with pool
9–16 OctIndividual Host,
€ 941 per night
4.97 out of 5 average rating, 76 reviews
Guest favourite
Flat in Greenport
The Crow's Nest
2–9 NovIndividual Host,
€ 248 per night
5.0 out of 5 average rating, 31 reviews

Quick stats about holiday rentals in Shelter Island Heights

Total rentals

290 properties

Rentals with a pool

90 properties have a pool

Pet-friendly rentals

100 properties allow pets

Family-friendly rentals

210 properties are a good fit for families

Total number of reviews

8.5K reviews

Nightly prices starting at

€ 92 before taxes and fees

Destinations to explore