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
$289 nightly
The price is $330 total per night
$330 total
Sep 7 - Sep 8
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 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
$196 nightly
The price is $222 total per night
$222 total
Sep 7 - Sep 8
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
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
2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

Westbrook CT
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
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
'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
Enchanted Waterfront Cottage

Enchanted Waterfront Cottage

Old Lyme CT
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Pet friendly
Charming 1920's no frills cottage in peaceful Old Saybrook

Charming 1920's no frills cottage in peaceful Old Saybrook

Old Saybrook CT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
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
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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
    $98 nightly
    The price is $113 total per night from Aug 10 to Aug 11
    $113 total
    Aug 10 - Aug 11
    Total with taxes and fees
    Sound View Greenport

    Sound View Greenport

    58775 County Rd 48 Greenport NY
    $351 nightly
    The price is $401 total per night from Sep 7 to Sep 8
    $401 total
    Sep 7 - Sep 8
    Total with taxes and fees
    Offshore Montauk

    Offshore Montauk

    71 S Emerson Ave Montauk NY
    $589 nightly
    The price is $673 total per night from Sep 7 to Sep 8
    $673 total
    Sep 7 - Sep 8
    Total with taxes and fees
    9.4/10 Exceptional! (171 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
215 Cottages
Lowest Price
$113
Highest Price
$673
Popular accommodation
North Fork Resort, 1-bedroom cottage with Grove Beach 🏖️ access., Cozy cottage on Fort Pond Lake., 2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard, Fairy Tale Guest Cottage in Magic Garden by Pool, 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., Enchanted Waterfront Cottage, Charming 1920's no frills cottage in peaceful Old Saybrook, Cozy cottage near downtown Clinton, Marina & Hammonasset Park