Photo by Erisa Dilo

Search Cottages in Shelter Island Heights

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Shelter Island Heights

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, (68)
"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, (8)
"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."
Sweet Cottage in Beach Community
'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 .
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.
Charming and Bright Cottage with Salt Water Pool
Smart TV

Charming and Bright Cottage with Salt Water Pool

10.0 out of 10, Exceptional, (6)
"What a beautiful cottage. Clean and bright. Would definitely stay again!"
Charming and Bright Cottage with Salt Water Pool
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, (71)
"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
Luxurious 3 BR Cottage w/ Ocean View Balcony
A heated pool

Luxurious 3 BR Cottage w/ Ocean View Balcony

10.0 out of 10, Exceptional, (1)
Luxurious 3 BR Cottage w/ Ocean View Balcony
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, (25)
"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 short walk to Chalker Beach
Smart TV, books

Charming 3-bedroom cottage short walk to Chalker Beach

10.0 out of 10, Exceptional, (1)
"We recently stayed here and have to say the owners went above and beyond our expectations!!! The home was just as described in the listing, very clean, organized and is in a great location. I would definitely stay here again. I would absolutely recommend this home for your next stay in CT.Thank you Karen for everything!!!"
Charming 3-bedroom cottage short walk to Chalker Beach
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, (13)
"We had a fantastic weekend at Nancy’s cottage in Flanders! The cottage is extremely comfortable - a nice sitting room, an open and well-lit kitchen, eating area, a spacious deck, and an incredible backyard (the best part). The bedrooms are comfortable as well. The backyard is set with a lovely deck We had a truly amazing time at this home! When we arrived we were greeted by Rick( the caretaker)with a helpful welcome binder and a truly beautiful house. It was clean, spacious and exactly what was...
CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE
Charming secluded island cottage
Outdoor dining

Charming secluded island cottage

Charming secluded island cottage
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

The price is AED 1,759
AED 3,496 total
includes taxes & fees
27 Jul - 28 Jul
Southampton cozy cottage by the beach
Charming Westbrook Cottage, Steps to Private Beach
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils

Charming Westbrook Cottage, Steps to Private Beach

9.8 out of 10, Exceptional, (6)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (26)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is AED 575
AED 1,153 total
includes taxes & fees
26 Jul - 27 Jul
1-bedroom cottage with Grove Beach 🏖️ access.
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, (15)
"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
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

10.0 out of 10, Exceptional, (1)
"We had the absolute best time! The property is right on the beach and you just can’t beat the view from your porch. Our toddlers loved being able to go back and forth throughout the day and it had all the amenities we could have asked for, even double ply toilet paper! Ely was a wonderful host and we’re looking forward to staying again in the future! "
Direct LI sound waterfront cottage, one level living in Hawks Nest Beach
Direct waterfront renovated cottage.
TV, books

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (74)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
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, (2)
"Wonderful stay in a remodeled stone house. Host was great and the house is very comfortable. We really enjoyed the beautifully restored building and all the touches throughout. "
The price is AED 1,157
AED 1,962 total
includes taxes & fees
16 Jul - 17 Jul
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
Enchanted Waterfront Cottage
Smart TV, fireplace, books

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"Easy process, owner was very responsive!"
Enchanted Waterfront Cottage
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Fridge, microwave, oven, stovetop

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

9.6 out of 10, Exceptional, (36)
"We had such a nice stay, the house was clean and had everything we needed."
The price is AED 970
AED 1,955 total
includes taxes & fees
16 Jul - 17 Jul
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

How much do cottages in Shelter Island Heights cost?
Rates for cottages in Shelter Island Heights range between AED 575 and AED 1,759 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 234 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.