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Search Cottages in Shelter Island Heights

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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 230 Cottages in Shelter Island Heights with updated reviews, rates, and availability.

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

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

9.0 out of 10, Wonderful, (22)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is SAR 330
SAR 649 total
includes taxes & fees
24 Mar - 25 Mar
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
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
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!
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)
"A five star review is not enough for this beautiful property! It is so well appointed, with everything you can possibly imagine to make your stay nothing less than perfect! It is an immaculate place that is decorated beautifully and the moment you open the door here you know you’ve chosen a charming and beautiful place to stay. The owner, Bill, was readily available prior to arriving to answer any questions we had. Even after we were here, he was in communication with us, which is always a...
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
'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
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
Classic Cottage in Best Private Community in Old Lyme CT.
Beach nearby, sun loungers, beach towels

Classic Cottage in Best Private Community in Old Lyme CT.

10.0 out of 10, Exceptional, (27)
"Great little house very close to the sound. Met our needs perfectly!"
Classic Cottage in Best Private Community in Old Lyme CT.
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 1,124 total
includes taxes & fees
10 Apr - 11 Apr
Orient Village — Historic Bayfront Cottage — 2025 Season
'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
Lovely Cottage in the Heart of Long Island Wine country
Beach

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (24)
"we had such a fun weekend out in southold! Cottage was perfect for us for a cold rainy weekend. Everything was so close to the house. Will definitely be back in the summer!"
Lovely Cottage in the Heart of Long Island Wine country
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
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!
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 1,121
SAR 2,118 total
includes taxes & fees
20 Mar - 21 Mar
Beach Cottage
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
Direct waterfront 3-bedroom cottage in Old Lyme, Hawks Nest Beach
Beach

Direct waterfront 3-bedroom cottage in Old Lyme, Hawks Nest Beach

Direct waterfront 3-bedroom cottage in Old Lyme, Hawks Nest Beach
Charming 3-bedroom cottage in fabulous Greenport
Beach towels

Charming 3-bedroom cottage in fabulous Greenport

Charming 3-bedroom cottage in fabulous Greenport
Charming Old Saybrook Cottage < 1 Mi to Beach
Fridge, microwave, stovetop, dishwasher

Charming Old Saybrook Cottage < 1 Mi to Beach

10.0 out of 10, Exceptional, (27)
"Was close to the beach and town. "
Charming Old Saybrook Cottage < 1 Mi to Beach
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 Heights

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1140)
"Great place. Love it in the off season for the quietness."
The price is SAR 491
SAR 634 total
includes taxes & fees
20 Mar - 21 Mar
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (366)
"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
24 Mar - 25 Mar
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)
"Great cozy place"
The price is SAR 494
SAR 646 total
includes taxes & fees
26 Mar - 27 Mar
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.

Frequently asked questions

How much do cottages in Shelter Island Heights cost?
Rates for cottages in Shelter Island Heights range between SAR 4 and SAR 1,121 per night. No matter your budget, you’ll find an ideal place to get in touch with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Shelter Island Heights?
You can choose from 230 cottages in Shelter Island Heights. Whether you’re traveling with the little ones or organizing a weekend escape with your closest amigos, Expedia can help you find the ideal space to enjoy the surrounding nature.
Why book your cottage in Shelter Island Heights with Expedia?
Expedia has some excellent cottages in Shelter Island Heights, so get set for a memorable stay close to nature. If you’re on a budget, select how much you’re willing to spend and the star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We’ll help you find the perfect digs whatever your escape looks like.
How can I find cheap cottages in Shelter Island Heights?
Expedia can help you easily track down cheap cottages in Shelter Island Heights. To book your perfect stay in a few quick keystrokes, try out our handy filter tool to refine your search results by budget, star rating and amenities.