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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select Shelter Island Cottages

Our top choices for Shelter Island cottages

1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (29)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is CA $161
CA $328 total
includes taxes & fees
Sep 1 - Sep 2
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 $692
CA $1,356 total
includes taxes & fees
Aug 24 - Aug 25
Southampton cozy cottage by the beach
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
On the beach

'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!
Smart TV

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (28)
"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.
Exterior

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
Exterior

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

9.4 out of 10, Exceptional, (8)
"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
Property grounds

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
Fridge, microwave, oven, stovetop

Sweet Cottage in Beach Community

10.0 out of 10, Exceptional, (11)
"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."
Sweet Cottage in Beach Community
Direct waterfront renovated cottage.
TV, books

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (78)
"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
Property grounds

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)!
Terrace/patio

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
Sun loungers

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
Property grounds

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

10.0 out of 10, Exceptional, (14)
"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
Beach

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

Charming 4-bedroom beach front cottage in beautiful Old Lyme Ct
DIRECT WATERFRONT PRIVATE BEACH
Private beach

DIRECT WATERFRONT PRIVATE BEACH

9.6 out of 10, Exceptional, (24)
"This rental was perfect. Super clean and comfy with the most amazing views. Loved that it’s right on the water with a private beach. We will definitely book this property again."
DIRECT WATERFRONT PRIVATE BEACH
Luxury Tiny Home In Niantic
Exterior

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"
The price is CA $361
CA $628 total
includes taxes & fees
Aug 27 - Aug 28
Luxury Tiny Home In Niantic
Town walking distance-Bridgehampton Cottage
Beach nearby

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
Interior

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
Property grounds

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 $437
CA $744 total
includes taxes & fees
Sep 1 - Sep 2
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
On the beach, sun loungers, beach towels

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

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Walkable to the beach. Have to cross a highway which was not as wide or busy, so it was easy."
Srini 2-night trip
Posted 1 day ago
Beachcomber Resort at Montauk