Compare Shelter Island Cottage Rentals

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Featured Cottages in Shelter Island

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3 out of 5
690 Queen St Greenport NY
$203 nightly
The price is $232 total per night
$232 total
May 19 - May 20
Total with taxes and fees
North Fork Cottages & RV 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 gift shop, barbecue grills, and a picnic area.
Pool
Pet friendly
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton CT
$199 nightly
The price is $225 total per night
$225 total
May 18 - May 19
Total with taxes and fees
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Air conditioning
'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.
Kitchen
Washer
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 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
$320 nightly
The price is $362 total per night
$362 total
May 18 - May 19
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
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.
Kitchen
Washer
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.
Kitchen
Washer
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.
Kitchen
Dryer
NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access

Clinton CT
$556 nightly
The price is $630 total per night
$630 total
May 17 - May 18
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Washer
Dryer
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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
    $593 nightly
    The price is $677 total per night from May 17 to May 18
    $677 total
    May 17 - May 18
    Total with taxes and fees
    8.4/10 Very Good! (779 reviews)
    Montauk Manor

    Montauk Manor

    236 Edgemere St. Montauk NY
    $185 nightly
    The price is $212 total per night from May 21 to May 22
    $212 total
    May 21 - May 22
    Total with taxes and fees
    9.2/10 Wonderful! (1,343 reviews)
    Montauk Yacht Club

    Montauk Yacht Club

    32 Star Island Rd Montauk NY
    $347 nightly
    The price is $396 total per night from May 17 to May 18
    $396 total
    May 17 - May 18
    Total with taxes and fees
    8.6/10 Excellent! (1,000 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
222 Cottages
Lowest Price
$212
Highest Price
$677
Popular accommodation
North Fork Cottages & RV 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 Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk, Cozy & Warm Getaway Cottage in Beach Community, 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