House holiday rentals in Shelter Island
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Top-rated house rentals in Shelter Island
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Shelter Island
House rentals with a pool
Home in East Hampton
4.93 out of 5 average rating, 140 reviews1800 Historical East Hampton Home, 1 Mile to Town!
30 Sep – 7 Oct
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
3–10 Oct
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
23–30 Oct
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
31 Oct – 7 Nov
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
9–16 Jan
Home in Sag Harbor
4.81 out of 5 average rating, 109 reviewsSag Harbor Gem, private, 4 Bedrooms, Pool w Summer
6–13 Jun
Home in Water Mill
4.91 out of 5 average rating, 110 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
16–23 Nov
Home in Manorville
4.98 out of 5 average rating, 199 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
3–10 Oct
Weekly house rentals
Home in Sag Harbor
4.97 out of 5 average rating, 124 reviewsRelax into Coastal Life at a Sun-Drenched Sag Harbor Home
24 Nov – 1 Dec
Home in Westbrook
4.86 out of 5 average rating, 135 reviewsFamily-Friendly Cottage by The Shore
9–16 Oct
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
12–19 May
Home in Shelter Island
4.88 out of 5 average rating, 69 reviewsCharming 4BR Cottage on Shelter Island
22–29 Dec
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
1–8 Sep
Home in East Marion
4.83 out of 5 average rating, 6 reviewsPrivate North Fork Cottage- Walk to Beach!
6–13 Nov
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
16–23 Oct
Home in Southold
5.0 out of 5 average rating, 16 reviewsLe Petit Cottage Southold NY
7–14 Nov
Private house rentals
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
11–18 Jun
Home in Sag Harbor
5.0 out of 5 average rating, 92 reviewsSecluded Modern Beach Style House
8–15 Jun
Home in Greenport
5.0 out of 5 average rating, 36 reviewsBeachfront Greenport Villa
8–15 Apr
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
19–26 Apr
Home in Greenport
5.0 out of 5 average rating, 70 reviewsBeach House in L.I. Wine Country
24–31 Oct
Home in Cutchogue
5.0 out of 5 average rating, 24 reviewsNorth Fork paradise between beaches and vineyards
6–13 Oct
Home in East Hampton
5.0 out of 5 average rating, 14 reviewsHistoric East Hampton Home - Private Beach Access
3–10 Oct
Home in Greenport
5.0 out of 5 average rating, 19 reviewsThe Corwin House
16–23 May
Quick stats about house rentals in Shelter Island
Total rentals
100 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
1.8K reviews
Nightly prices starting at
€ 112 before taxes and fees
Destinations to explore
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