Compare Shelter Island Cottage Rentals

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Featured Shelter Island Cottages

Direct waterfront renovated cottage.

Direct waterfront renovated cottage.

At this cottage, guests have access to features like laundry facilities. This beach cottage also has a garden.
Kitchen
Washer
Fabulous Waterfront Property in the Heart of Wine Country

Fabulous Waterfront Property in the Heart of Wine Country

Guests of this cottage enjoy access to a water park, laundry facilities, and a garden. This family-friendly cottage also has 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 .

Guests of this cottage enjoy access to a water park, laundry facilities, and a garden. This beach cottage also has barbecue grills.
Kitchen
Washer
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

$157 nightly
The price is $178 total per night
$178 total
Oct 21 - Oct 22
Total with taxes and fees
At this cottage, guests have access to barbecue grills.
Kitchen
Air conditioning
Sweet Cottage in Beach Community

Sweet Cottage in Beach Community

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

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

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

2 out of 5
$286 nightly
The price is $324 total per night
$324 total
Nov 5 - Nov 6
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
The gardners Cottage 1 mile from long Island Sound - pet friendly

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

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Dryer
Southampton cozy cottage by the beach

Southampton cozy cottage by the beach

$423 nightly
The price is $483 total per night
$483 total
Oct 20 - Oct 21
Total with taxes and fees
At this cottage, guests have access to barbecue grills.
Pet friendly
Free WiFi
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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

    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd, Old Saybrook, CT
    $89 nightly
    The price is $102 total per night from Oct 19 to Oct 20
    $102 total
    Oct 19 - Oct 20
    Total with taxes and fees
    7.8/10 Good! (1,007 reviews)
    Gurney's Montauk Resort & Seawater Spa

    Gurney's Montauk Resort & Seawater Spa

    290 Old Montauk Highway, Montauk, NY
    $358 nightly
    The price is $409 total per night from Nov 4 to Nov 5
    $409 total
    Nov 4 - Nov 5
    Total with taxes and fees
    8.2/10 Very Good! (670 reviews)
    Quality Inn Old Saybrook - Westbrook

    Quality Inn Old Saybrook - Westbrook

    100 Essex Rd, Old Saybrook, CT
    $94 nightly
    The price is $108 total per night from Nov 2 to Nov 3
    $108 total
    Nov 2 - Nov 3
    Total with taxes and fees
    7.6/10 Good! (1,005 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
209 Cottages
Lowest Price
$102
Highest Price
$483
Popular accommodation
Direct waterfront renovated cottage. , Fabulous Waterfront Property in the Heart of Wine Country, 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., 1-bedroom cottage with Grove Beach 🏖️ access., Sweet Cottage in Beach Community, Cozy cottage near downtown Clinton, Marina & Hammonasset Park, Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk, The gardners Cottage 1 mile from long Island Sound - pet friendly, Southampton cozy cottage by the beach