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Search Shelter Island Cottage Rentals from CA $176

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Shelter Island Cottages

1-bedroom cottage with Grove Beach 🏖️ access.
Enjoy a casual outdoor space with a front porch, potted plant, and Adirondack chairs.

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (28)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is CA $176
CA $343 total
includes taxes & fees
Aug 12 - Aug 13
1-bedroom cottage with Grove Beach 🏖️ access.
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
The price is CA $962
CA $1,704 total
includes taxes & fees
Aug 14 - Aug 15
Southampton cozy cottage by the beach
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Situated in a lush environment, this two-story house features a wooden door and windows, surrounded by trees and shrubs, with a garden in the foreground.

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Location and views! Located directly on Shinnecock Bay!
Relax in a comfortable living area with a flat-screen TV, sofa, and dining table.

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (27)
"Cute beach bungalow vibe. The outdoor space, grill, and firepit made this property worthwhile! Lori's a wonderful, accomodating host."
Location and views! Located directly on Shinnecock Bay!
Cozy cottage on Fort Pond Lake.
Situated lakeside, this charming building features a large American flag on its roof and a garage door.

Cozy cottage on Fort Pond Lake.

10.0 out of 10, Exceptional, (16)
"The lake house was a perfect retreat, perfectly located to town, train, trails and beach. We can’t wait to visit again !"
Cozy cottage on Fort Pond Lake.
Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach
Stunning historical building with a central tower and traditional pitched roof.

Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach

9.2 out of 10, Wonderful, (7)
"It was nice and relaxing...walking, swimming, biking, kayaking and beaching. The house was super cool...150 years old! Nice old fashioned laid back beach vacation! Mary the host was wonderful!"
Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach
Fairy Tale Guest Cottage in Magic Garden by Pool
Charming single-story house with a front entrance, porch, and well-manicured lawn.

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool
Sweet Cottage in Beach Community
Stroll along the garden pathway to a charming home with a cozy porch and lush surroundings.

Sweet Cottage in Beach Community

10.0 out of 10, Exceptional, (10)
"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."
Sweet Cottage in Beach Community
Direct waterfront renovated cottage.
Enjoy outdoor dining or relaxation on the covered patio with comfortable seating and tables.

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (77)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
The gardners Cottage 1 mile from long Island Sound - pet friendly
Traditional cottage with a front porch and garden, offering a peaceful retreat.

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (16)
"Robin was a great resource about the area. Her property was amazing the cottage was fantastic. Very comfortable and clean. We had a relaxing stay and a great time. We would love to go back again and again!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Relax on the porch with a view of lush greenery, featuring a wicker sofa and a small table.

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (115)
"Lovely cottage on the Peconic Bay. We enjoyed our stay; found more than everything we needed. "
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Lovely Cottage in the Heart of Long Island Wine country
Cozy cabin with a front porch, surrounded by a deck and a fenced yard, perfect for outdoor dining and relaxation.

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (26)
"Our family stayed at this quaint cottage in the North Fork. The cottage has a nice kitchen, gas fireplace, and well appointed bedrooms. I would love to visit in summer, it must be wonderful!"
Lovely Cottage in the Heart of Long Island Wine country
CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE
Relax on the ocean-view deck with a wooden railing, surrounded by lush greenery and a small table for dining or relaxation.

CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE

10.0 out of 10, Exceptional, (13)
"We had a wonderful stay here while visiting for a wedding. the bedrooms were both upstairs, FYI which I wasn't aware of from the listing but we made it work. The grounds were beautiful and lots of birds to enjoy. "
CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE
Charming 4-bedroom beach front cottage in beautiful Old Lyme Ct
Exterior

Charming 4-bedroom beach front cottage in beautiful Old Lyme Ct

Charming 4-bedroom beach front cottage in beautiful Old Lyme Ct
Beachfront Cottage with panoramic views of Long Island Sound in Madison CT
Exterior

Beachfront Cottage with panoramic views of Long Island Sound in Madison CT

Beachfront Cottage with panoramic views of Long Island Sound in Madison CT
Luxury Tiny Home In Niantic
Situated in a forested area, this cabin features a cozy front porch with a seating area and a stone wall.

Luxury Tiny Home In Niantic

10.0 out of 10, Exceptional, (4)
"This property is perfect for 2-3 guests and located within short distance to town. The house is well built and very clean. Five Stars"
Luxury Tiny Home In Niantic
Town walking distance-Bridgehampton Cottage
Situated in a lush environment, this charming house features a front porch and well-maintained gardens.

Town walking distance-Bridgehampton Cottage

9.4 out of 10, Exceptional, (10)
"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."
Town walking distance-Bridgehampton Cottage
Direct LI sound waterfront cottage, one level living in Hawks Nest Beach
Stylish single-story home with a gabled roof and chimney, featuring a front entrance and wooden deck.

Direct LI sound waterfront cottage, one level living in Hawks Nest Beach

9.0 out of 10, Wonderful, (2)
"Perfect little beachfront cottage right on the water ...a few steps across your own beach. We had a very relaxing, comfortable visit."
Direct LI sound waterfront cottage, one level living in Hawks Nest Beach
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
Surrounded by lush greenery, this charming house boasts a cozy balcony overlooking the forest.

Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more

10.0 out of 10, Exceptional, (3)
"Lovely location and host."
The price is CA $433
CA $735 total
includes taxes & fees
Aug 17 - Aug 18
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Enjoy ocean views and outdoor activities in a serene backyard with a covered grill area and deck.

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

9.8 out of 10, Exceptional, (72)
"We stayed at this property last year and again this year. You can’t beat the location and the house is perfect for a group of family or friends. We had a lovely time and look forward to another stay in the future!"
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Thank you Adrian. She was wonderful and made my mother’s birthday special. Every interaction we had with the staff was positive. The halyard served a delicious lobster roll in a beautiful setting. We will be back. "
Joseph 1-night trip
Posted 1 day ago
Sound View Greenport