Compare Shelter Island Cottage Rentals

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Featured Shelter Island Cottages

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3 out of 5
690 Queen St Greenport NY
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, a picnic area, and barbecue grills.
Pool
Pet friendly
'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 of this cottage enjoy access to a water park, laundry facilities, and a garden. This beach cottage also has barbecue grills.
Kitchen
Washer
RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.

RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.

Westbrook CT
Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This family-friendly cottage also has barbecue grills.
Pool
Hot Tub
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
Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach

Hampton Bays NY
$398 nightly
The price is $455 total per night
$455 total
Dec 4 - Dec 5
Total with taxes and fees
At this cottage, guests have access to barbecue grills.
Kitchen
Pet friendly
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
Lovely Cottage in the Heart of Long Island Wine country

Lovely Cottage in the Heart of Long Island Wine country

Southold NY
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Free WiFi
Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town

Westbrook CT
At this cottage, guests have access to barbecue grills.
Kitchen
Pet friendly
Charming 3-bedroom cottage short walk to Chalker Beach

Charming 3-bedroom cottage short walk to Chalker Beach

Old Saybrook CT
Guests staying at this cottage have access to laundry facilities, barbecue grills, and 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
    $280 nightly
    The price is $320 total per night from Dec 11 to Dec 12
    $320 total
    Dec 11 - Dec 12
    Total with taxes and fees
    8.2/10 Very Good! (694 reviews)
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd Old Saybrook CT
    $73 nightly
    The price is $85 total per night from Dec 9 to Dec 10
    $85 total
    Dec 9 - Dec 10
    Total with taxes and fees
    7.8/10 Good! (1,002 reviews)
    Sound View Greenport

    Sound View Greenport

    58775 County Rd 48 Greenport NY
    $203 nightly
    The price is $232 total per night from Dec 2 to Dec 3
    $232 total
    Dec 2 - Dec 3
    Total with taxes and fees
    8.4/10 Very Good! (593 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
204 Cottages
Lowest Price
$85
Highest Price
$455
Popular accommodation
North Fork Cottages & RV Resort, 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston., Direct waterfront renovated cottage. , Seabreeze #3: Cozy Cottage by the beach, Totally Renovated Cottage on the North Fork 7 min. walk to the Beach, Lovely Cottage in the Heart of Long Island Wine country, Adorable Cottage with Cottage porch, walk to water & town, Charming 3-bedroom cottage short walk to Chalker Beach