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
$273 nightly
The price is $312 total per night
$312 total
Jun 9 - Jun 10
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. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include a picnic area, a gift shop, and barbecue grills.
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton CT
$159 nightly
The price is $180 total per night
$180 total
Jun 4 - Jun 5
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
'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, barbecue grills, and a garden.
Fairy Tale Guest Cottage in Magic Garden by Pool

Fairy Tale Guest Cottage in Magic Garden by Pool

Bridgehampton NY
At this cottage, guests have access to an outdoor pool and a garden.
Pool
Free WiFi
Cozy & Warm Getaway Cottage in Beach Community

Cozy & Warm Getaway Cottage in Beach Community

Niantic CT
At this cottage, guests have access to a gym, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Waterford CT
$347 nightly
The price is $393 total per night
$393 total
Jun 8 - Jun 9
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.

1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.

Water Mill NY
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton CT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access

Clinton CT
$236 nightly
The price is $268 total per night
$268 total
Jun 3 - Jun 4
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
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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
    $781 nightly
    The price is $892 total per night from Jun 11 to Jun 12
    $892 total
    Jun 11 - Jun 12
    Total with taxes and fees
    8.4/10 Very Good! (789 reviews)
    Montauk Manor

    Montauk Manor

    236 Edgemere St. Montauk NY
    $286 nightly
    The price is $327 total per night from Jun 3 to Jun 4
    $327 total
    Jun 3 - Jun 4
    Total with taxes and fees
    9.2/10 Wonderful! (1,355 reviews)
    The Atlantic Hotel

    The Atlantic Hotel

    1655 County Road 39 Southampton NY
    $221 nightly
    The price is $252 total per night from Jun 3 to Jun 4
    $252 total
    Jun 3 - Jun 4
    Total with taxes and fees
    7.2/10 Good! (1,002 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
230 Cottages
Lowest Price
$180
Highest Price
$892
Popular accommodation
North Fork Resort, 1-bedroom cottage with Grove Beach 🏖️ access., 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., Fairy Tale Guest Cottage in Magic Garden by Pool, Cozy & Warm Getaway Cottage in Beach Community, Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk, 1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum. , The gardners Cottage 1 mile from long Island Sound - pet friendly, NEW Coastal Cottage 2 Miles to Beach + Lake Access