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Search Vacation Homes in Shelter Island

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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Vacation Homes in Shelter Island

Surf Cottage - Steps from Surf Lodge, Town, and Beach
Beach nearby, beach towels

Surf Cottage - Steps from Surf Lodge, Town, and Beach

9.6 out of 10, Exceptional, (72)
"Our home away from home"
Surf Cottage - Steps from Surf Lodge, Town, and Beach
3-bedroom Montauk Coastal Getaway
Microwave, oven, stovetop, dishwasher

3-bedroom Montauk Coastal Getaway

3-bedroom Montauk Coastal Getaway
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Pool

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

10.0 out of 10, Exceptional, (4)
"Great property for two people right next to the downtown. Our stay was comfortable and clean!"
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Large Charming Historic House close to Beaches
Fridge, microwave, oven, dishwasher

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (24)
"Had a wonderful stay. The house was large enough to allow us all to have our own rooms. Location was perfect and within walking distance of everything. "
Large Charming Historic House close to Beaches
The Cooper-Burke House
Beach nearby, beach towels

The Cooper-Burke House

10.0 out of 10, Exceptional, (26)
"Nice location and house "
The Cooper-Burke House
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Smart TV, fireplace, stereo

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (85)
"Rick was a gracious host; the house was clean, and the beach was nearby. We enjoyed our stay "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (7)
"Great place! Great communication with property owner!"
The price is SAR 827
SAR 1,733 total
includes taxes & fees
9 Jun - 10 Jun
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
On the beach

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

2.0 out of 10, (1)
"upon arrival to the house, they did not give us clear information as to which floor we were staying on. They gave us the information for both the first floor and the second floor without telling us which floor was ours. Then after checking in, we asked for the Wi-Fi password and had some other questions to which they did not respond or answer ever. At the end of our stay, they contacted Verbo directly and tried to charge me an additional 730. Safe to say I will never be booking with them again."
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
Stunning Waterfront Home with Private Beach!
Aerial view

Stunning Waterfront Home with Private Beach!

10.0 out of 10, Exceptional, (43)
"The property is immaculate, so clean and peaceful, views are stunning. Can’t recommend enough."
Stunning Waterfront Home with Private Beach!
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Smart TV, fireplace, printers

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

10.0 out of 10, Exceptional, (1)
"Great location to see all the eastern LI towns. The house is well appointed and nicely decorated. Easy communication with the host. "
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Cozy Westbrook Vacation Rental - Walk to Beach!
Aerial view

Cozy Westbrook Vacation Rental - Walk to Beach!

9.8 out of 10, Exceptional, (20)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!
Escape to Sag Harbor
Interior

Escape to Sag Harbor

10.0 out of 10, Exceptional, (47)
"Amazing house and location!! Would stay again "
Escape to Sag Harbor
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
A heated pool

Newly built ranch, beautifully landscaped with pool, large yard, patio,...

10.0 out of 10, Exceptional, (20)
"This property was gorgeous! It’s conveniently located right in the heart of Greenport and the nearby private beach was stunning! Highly recommend this location, can only imagine how perfect it’d be for the summer time!"
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
The SandPiper
Terrace/patio

The SandPiper

9.8 out of 10, Exceptional, (22)
"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
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
On the beach, sun loungers

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

10.0 out of 10, Exceptional, (19)
""Waterfront beauty in Niantic, CT.Ocean views, peaceful great place "
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
Historic Essex Home w/ Large Yard Near Downtown!
TV

Historic Essex Home w/ Large Yard Near Downtown!

10.0 out of 10, Exceptional, (48)
"A lovely home in a great area! We will be back!"
Historic Essex Home w/ Large Yard Near Downtown!
Charming beach home, complete with pool & cozy guest house!
Interior

Charming beach home, complete with pool & cozy guest house!

9.6 out of 10, Exceptional, (25)
"Wonderful property. Plenty of room for 7 adults. Would definitely stay there again. "
Charming beach home, complete with pool & cozy guest house!
Unique Modern Barn House in Sag Harbor
Smart TV, fireplace

Unique Modern Barn House in Sag Harbor

10.0 out of 10, Exceptional, (17)
"My family and I rented the house over the holidays and had an amazing stay. The house has great amenities and George was very attentive and helpful. Would definitely recommend and stay again "
Unique Modern Barn House in Sag Harbor
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
Fridge, microwave, oven, stovetop

Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

10.0 out of 10, Exceptional, (35)
"As advertised. Great spot and house. "
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
Aqua Vista
Sun loungers, beach towels

Aqua Vista

10.0 out of 10, Exceptional, (14)
"Place was very clean and easy to access. Great location for anyone staying in the area. Host was easy to talk to and very helpful in finding places nearby to visit. "
Aqua Vista
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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