Compare Shelter Island Cottage Rentals

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Featured Shelter Island Cottages

Fairy Tale Guest Cottage in Magic Garden by Pool

Fairy Tale Guest Cottage in Magic Garden by Pool

At this cottage, guests have access to an outdoor pool and a garden.
Pool
Kitchen
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
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Cozy cottage on Fort Pond Lake.

Cozy cottage on Fort Pond Lake.

At this cottage, guests have access to features like local meal delivery service. This smoke-free cottage also has barbecue grills.
Kitchen
Pet friendly
Location and views! Located directly on Shinnecock Bay!

Location and views! Located directly on Shinnecock Bay!

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

At this cottage, guests have access to barbecue grills.
Kitchen
Air conditioning
Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday

Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has 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
Charming and Bright Cottage with Salt Water Pool

Charming and Bright Cottage with Salt Water Pool

At this cottage, guests have access to a garden.
Pool
Kitchen
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, a garden, and barbecue grills.
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

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
229 Cottages
Lowest Price
Highest Price
Popular accommodation
Fairy Tale Guest Cottage in Magic Garden by Pool, Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk, Cozy cottage on Fort Pond Lake., Location and views! Located directly on Shinnecock Bay!, 1-bedroom cottage with Grove Beach 🏖️ access., Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday, The gardners Cottage 1 mile from long Island Sound - pet friendly, Charming and Bright Cottage with Salt Water Pool, Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Cottages in Shelter Island

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