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Shelter Island Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Shelter Island Vacation Homes

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Relax by the serene pool surrounded by tall trees and a well-maintained lawn.

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (12)
"Great place! Great communication with property owner!"
The price is CA $403
CA $764 total
includes taxes & fees
Aug 8 - Aug 9
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Hamptons Retreat
Terrace/patio

Hamptons Retreat

Hamptons Retreat
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Outdoor spa tub

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (133)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Stunning Hampton Holiday Family Fantasy for your Team
Relax in a spacious room with expansive views of the surrounding greenery, featuring a comfortable seating area and a glass door leading to an outdoor patio.

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (69)
"Everything was great!!!"
Stunning Hampton Holiday Family Fantasy for your Team
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
Walk along the beach, flanked by pine trees and a wooden fence.

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

10.0 out of 10, Exceptional, (1)
"Perfect location."
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Relax by the serene pool surrounded by lush greenery and mature trees.

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (29)
"We stayed here for my friend’s bachelorette party and it was perfect for what we needed! Dave even allowed us to check in a little early to decorate for her arrival! Would definitely stay again!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Cozy sun drenched beach cottage private beach, walk to town, hot tub
Property grounds

Cozy sun drenched beach cottage private beach, walk to town, hot tub

9.8 out of 10, Exceptional, (20)
"A very cozy and peaceful escape, loved the hot tub!"
Cozy sun drenched beach cottage private beach, walk to town, hot tub
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
Relax in this spacious living area with a mezzanine level, plush sofa, and modern kitchen.

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

10.0 out of 10, Exceptional, (6)
"The is great!!! Very convenient location and plenty to do."
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking
Enjoy the serene beach scene with a clear view of the ocean and a picturesque wooden fence.

Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

10.0 out of 10, Exceptional, (38)
"Very clean well kept property near beach - host very welcoming and receptive. Enjoyed our stay!"
Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking
The Cooper-Burke House
Relax on the beach with a bench and picnic table nearby, surrounded by a natural wooden fence.

The Cooper-Burke House

10.0 out of 10, Exceptional, (27)
"Nice location and house "
The Cooper-Burke House
Another rental season is coming up.
Relax by the pool surrounded by a covered seating area and lounge chairs.

Another rental season is coming up.

10.0 out of 10, Exceptional, (18)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Another rental season is coming up.
Walk to town, Bike to beach, Private pool oasis !
Relax by the serene pool surrounded by lush greenery.

Walk to town, Bike to beach, Private pool oasis !

10.0 out of 10, Exceptional, (18)
"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."
Walk to town, Bike to beach, Private pool oasis !
Work and Play Special! Extended Stay Discount
Relax by the pool surrounded by lush gardens and comfortable lounge chairs.

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (48)
"We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!"
The price is CA $1,241
CA $2,143 total
includes taxes & fees
Sep 4 - Sep 5
Work and Play Special! Extended Stay Discount
Brand New Waterfront - Chic & Sophisticated unit #701
Relax on the seating area with a sofa and chairs, surrounded by a pergola with string lights.

Brand New Waterfront - Chic & Sophisticated unit #701

10.0 out of 10, Exceptional, (3)
"Great home and location. Enjoyed our stay!"
Brand New Waterfront - Chic & Sophisticated unit #701
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Relax on the deck overlooking the serene water's edge, where you can enjoy a meal or unwind in a peaceful setting.

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (133)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Charming Village home in the heart of Southampton
Cozy up by the fireplace, surrounded by abstract art and lush views.

Charming Village home in the heart of Southampton

10.0 out of 10, Exceptional, (22)
"Great location, clean, easy checkin, slept 7 comfortably"
Charming Village home in the heart of Southampton
The SandPiper
Relax on the covered porch with a single chair and small table, surrounded by lush greenery and a residential neighborhood view.

The SandPiper

9.8 out of 10, Exceptional, (24)
"My friends and I stayed here for a night after a wedding. It was the perfect place to stay after a long day. Host was kind and helpful with anything I needed! "
The SandPiper
American Beech in Greenport - Petite King Room 7
Enjoy dining al fresco in a serene outdoor setting with lush greenery and ambient lighting.

American Beech in Greenport - Petite King Room 7

8.8 out of 10, Excellent, (3)
"We thoroughly enjoyed our stay!"
The price is CA $328
CA $491 total
includes taxes & fees
Aug 14 - Aug 15
American Beech in Greenport - Petite King Room 7
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
Relax on the beach with two comfortable chairs facing the calm sea, overlooking a wooden pier extending into the water.

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

4.8 out of 10, (3)
"Overall, my girlfriends and I had a good stay at this accommodation. Transparently, there were some hiccups in communication between the property manager and I in the week leading up to our trip that were not clearly stated in the home's description prior to us booking our stay, however, I felt that they were able to address my concerns and came up with solutions that felt satisfactory to my group and I. The property manager was overall understanding and receptive to my feedback through our...
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms
Relax by the serene pool surrounded by lush greenery and a stunning sea view.

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

10.0 out of 10, Exceptional, (32)
"This home fit everyone perfectly. The great room was a stunner and the bay views awesome! "
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms
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 Hotel Reviews

Greenporter Hotel

Greenporter Hotel

10/10 Excellent
"Everything was perfect!"
Elina 1-night trip
Posted 11 hours ago
Greenporter Hotel