Compare Shelter Island Cottage Rentals

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Featured Cottages in Shelter Island

North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
$267 nightly
The price is $305 total per night
$305 total
Oct 22 - Oct 23
Total with taxes and fees
North Fork Resort features free WiFi in public areas, a seasonal outdoor pool, and laundry facilities. If you decide to drive, there's free parking. Additional amenities include a gift shop, a picnic area, and barbecue grills.
Pool
Pet friendly
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton CT
$183 nightly
The price is $207 total per night
$207 total
Oct 21 - Oct 22
Total with taxes and fees
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Air conditioning
Cozy cottage on Fort Pond Lake.

Cozy cottage on Fort Pond Lake.

Montauk NY
At this cottage, guests have access to features like local meal delivery service. This smoke-free cottage also has barbecue grills.
Kitchen
Pet friendly
Cottage on Beach front Estate Walk to Village

Cottage on Beach front Estate Walk to Village

greenport NY
At this cottage, guests have access to features like laundry facilities. This beach cottage also has barbecue grills.
Kitchen
Washer
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

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

Cutchogue NY
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

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

greenport NY
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton CT
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Fabulous Waterfront Property in the Heart of Wine Country

Fabulous Waterfront Property in the Heart of Wine Country

Peconic NY
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Direct waterfront renovated cottage.

Direct waterfront renovated cottage.

Madison CT
At this cottage, guests have access to features like laundry facilities. This beach cottage also has a garden.
Kitchen
Washer
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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.

Hotel Options in Shelter Island

    Gurney's Montauk Resort & Seawater Spa

    Gurney's Montauk Resort & Seawater Spa

    290 Old Montauk Highway Montauk NY
    $397 nightly
    The price is $454 total per night from Nov 10 to Nov 11
    $454 total
    Nov 10 - Nov 11
    Total with taxes and fees
    Water's Edge Resort & Spa

    Water's Edge Resort & Spa

    1525 Boston Post Road Westbrook CT
    $216 nightly
    The price is $248 total per night from Nov 3 to Nov 4
    $248 total
    Nov 3 - Nov 4
    Total with taxes and fees
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd Old Saybrook CT
    $77 nightly
    The price is $89 total per night from Oct 19 to Oct 20
    $89 total
    Oct 19 - Oct 20
    Total with taxes and fees
    8/10 Very Good! (1,003 reviews)

Cottages

Book a cottage in Shelter Island
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Shelter Island. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Shelter Island better.

Cottage apartments in Shelter Island range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Shelter Island
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Shelter Island and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Shelter Island cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Shelter Island. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Shelter Island Cottages essential information

Accommodation
201 Cottages
Lowest Price
$89
Highest Price
$454
Popular accommodation
North Fork Resort, 1-bedroom cottage with Grove Beach 🏖️ access., Cozy cottage on Fort Pond Lake., Cottage on Beach front Estate Walk to Village, 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 ., Cozy cottage near downtown Clinton, Marina & Hammonasset Park, Fabulous Waterfront Property in the Heart of Wine Country, Direct waterfront renovated cottage.