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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 225 Cottages in Shelter Island with updated reviews, rates, and availability.

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Living area

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Charming 3-bedroom cottage short walk to Chalker Beach
Smart TV, books

Charming 3-bedroom cottage short walk to Chalker Beach

Charming 3-bedroom cottage short walk to Chalker Beach
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
Smart TV

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.2 out of 10, Wonderful, (23)
"Always a pleasure staying here!"
The price is SAR 356
SAR 679 total
includes taxes & fees
6 Apr - 7 Apr
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
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, (13)
"The cottage is cozy and clean. It has everything I need. and perfect for me and my dogs. We enjoyed our stay and had a nice winter break. We hope to come back next year. Thank you, Robin!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Enchanted Waterfront Cottage
Smart TV, fireplace, books

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
Orient Village — Historic Bayfront Cottage — 2025 Season
Exterior

Orient Village — Historic Bayfront Cottage — 2025 Season

10.0 out of 10, Exceptional, (20)
"We had an amazing time enjoying the house and exploring the area. Fishing wasn’t fantastic, but that’s nobody’s fault. Would definitely go back!"
The price is SAR 4
SAR 1,125 total
includes taxes & fees
10 Apr - 11 Apr
Orient Village — Historic Bayfront Cottage — 2025 Season
Hampton Cottage.
Smart TV

Hampton Cottage.

10.0 out of 10, Exceptional, (3)
"we had a great stay at this property. the house was perfect. great value for the price. it is new and modern and extremely clean. the area itself was also nice. on a dead end street so nice and secluded. the host also included many amenities for guests to use which was a plus. would definitely stay here again. "
The price is SAR 784
SAR 1,103 total
includes taxes & fees
6 Apr - 7 Apr
Hampton Cottage.
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Miscellaneous

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

9.8 out of 10, Exceptional, (91)
"We stayed for the weekend and couldn't have had a better time! The home is clean and lovely with a well stocked kitchen, comfortable beds and an unbeatable views! Very close to wineries, downtown Greenport and the Shelter Island ferry. Patrick, the owner, had great tips on local activities and was an all around great guy. Thank you! We'll be back! Patrick"
'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!

9.2 out of 10, Wonderful, (23)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun loungers, beach towels

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Charming Old Lyme Cottage, Steps to Private Beach!
Coffee/tea maker

Charming Old Lyme Cottage, Steps to Private Beach!

8.6 out of 10, Excellent, (7)
"We booked last minute as we decided to join family staying in Old Lyme. This cottage was just perfect for our needs. My husband and I along with our 19 year old stayed here. Clean, newly remodeled and amenities to meet our needs for a 3 day beach retreat. Simple, but practical. Close to beach and a/c was a treat during the heat wave! ⭐️⭐️⭐️⭐️⭐️"
Charming Old Lyme Cottage, Steps to Private Beach!
Charming Westbrook Cottage, Steps to Private Beach
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils

Charming Westbrook Cottage, Steps to Private Beach

10.0 out of 10, Exceptional, (2)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (70)
"We had a magical Christmas here. I fulfilled a lifelong dream to host my family for Christmas Eve Smorgasbord and the jigsaw puzzle had all of the pieces! "
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Beach nearby, sun loungers

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

10.0 out of 10, Exceptional, (14)
"This rental is so unique with the 2 sides, and was absolutely perfect for our wedding weekend. We had the groom’s friends staying on one side, and my friends staying on the other side. The two sides are connected through the sunroom and the backyard space is great which made bringing the whole group together so easy. The setup was also perfect for me to get ready on my own separate side the day of the wedding so that my now husband wouldn’t see me. The decor and cleanliness of the house were...
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Beach nearby, sun loungers, beach towels

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

10.0 out of 10, Exceptional, (25)
"Before my trip even began, communication with Bill was exceptional. Bill was very responsive throughout my entire 3 day stay. The entire house was recently renovated, and I can tell not only did they invest a lot of money in the renovation, but they were very thoughtful in all the upgrades they made. The neighborhood is also very peaceful. Whether you make a left or right, you’re only a couple blocks from the beach. My wife and I really enjoyed staying at this house. It was perfect for us as a...
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Direct waterfront renovated cottage.
TV, books

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (71)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Beach nearby

'Grandma's Cottage' w/ Sunroom: Walk to Beach

8.0 out of 10, Very Good, (3)
"Terrific location. 1 block from the beach."
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Beach Cottage
Fridge, microwave, oven, stovetop

Beach Cottage

10.0 out of 10, Exceptional, (3)
"Excellent experience. Great host. Clean, inviting property near beach. Cozy home. Good value. Will stay again. Thank you. "
The price is SAR 1,122
SAR 2,118 total
includes taxes & fees
2 Apr - 3 Apr
Beach Cottage
Hamptons Vacation Rental w/ Seasonal Pool!
Fridge, microwave, stovetop, dishwasher

Hamptons Vacation Rental w/ Seasonal Pool!

10.0 out of 10, Exceptional, (5)
"My family enjoyed staying at this lovely property. The backyard was especially great! My kids splashed in the heated pool and jumped on the trampoline every day! The location was ideal and very close to the beach. We would definitely return. "
Hamptons Vacation Rental w/ Seasonal Pool!
Charming 3-bedroom cottage in fabulous Greenport
Beach towels

Charming 3-bedroom cottage in fabulous Greenport

Charming 3-bedroom cottage in fabulous Greenport
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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Other property types in Shelter Island

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1143)
"the location is great and price is reasonable. "
The price is SAR 536
SAR 685 total
includes taxes & fees
14 Apr - 15 Apr
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (367)
"Had a great stay here . Staff was friendly and check in and out was a breeze . Was very clean and comfortable. Only complaint was I couldn’t get a hot shower . Otherwise place is excellent. Shops , restaurants and bars are all a short walk . "
The price is SAR 510
SAR 624 total
includes taxes & fees
9 Apr - 10 Apr
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"2nd loft bedroom/bath was especially nice"
The price is SAR 494
SAR 646 total
includes taxes & fees
8 Apr - 9 Apr
Windward Shores Ocean Resort
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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