Top Shelter Island Holiday Cottages in 2025

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Featured Cottages in Shelter Island

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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.

Immerse yourself in local style in Shelter Island Cottages

If you're the sort of traveller who finds yourself seeking out local architecture wherever you visit, and relish the idea of getting a real feel for the cultural identity of destination as embodied by the local landmarks, then you'll probably love Shelter Island Cottages. That's because local styles and local architecture are what tend to set a cottage apart from the crowd. There's none of the cookie-cutter looks of large-scale hotels to be found in this type of accommodation. It's all about immersing yourself in the styles of the region – something that culture lovers are bound to enjoy. Just be ready to wake up in a place that really fits the bill and channels the Shelter Island vibe.

Getting cosy in Shelter Island Cottages

There are few accommodation types in Shelter Island that will have you feeling quite as cosy as a cottage. Quaint and charming, these little boltholes might be just a bed and a bathroom, snug and compact and nestled in their very own little gardens. Others are larger, suited to families looking for somewhere warm and welcoming. They could pack in kitchen areas and dining rooms, lounges with real fires or cushiony sofas, TVs and outdoor porches for curling up and watching the world go by.

A stay in a holiday cottage also brings the added comfort of seclusion. Whether you're a pair of honeymooners in search of somewhere a little more private than a sprawling holiday resort, or a family who need just a tad extra space to spread out, you can rest assured that you'll get it by opting for a cottage from ebookers.

Save money on Shelter Island Cottages

Shelter Island Cottages don't have to break the bank. Far from it. These cosy little nooks could actually help you save money on that next adventure. For starters, they tend to be smaller and more compact than large-scale pads, making them an affordable alternative to other popular family accommodations. What's more, many come with on-site kitchen areas. That means you can rustle up your own food whenever you want, using tasty produce from local markets and drinking wines from local farms. That all saves plenty, especially if you're skipping restaurant trips for the whole family.

Search ebookers to choose the best Shelter Island Cottages

With such a wide range of Shelter Island Cottages on offer on ebookers, you might think it would be tricky to home in on the one that's perfect for you. That's where our accommodation search and travel map come in. They let you filter out all other hotel types and discard cottages that don't have the facilities you're after. And you'll be able to zoom in and out of the destination to discover that hidden holiday cottage you've been pining for. All you need to do is enter the dates you're planning on travelling and ebookers will do the rest.

Shelter Island Cottages essential information

Accommodation
179 Cottages
Lowest Price
€188
Highest Price
€188
Popular accommodation
Beach Bungalow, large porch, 1/2 mile to the water. , 1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets, Luxury Cottage walking distance to Saybrook Point Marina, 2 King Beds, Fabulous Waterfront Property in the Heart of Wine Country, Pace's Place Close to North Fork Vineyards, Walk to Love Lane! Immaculately renovated private cottage., Beach access Cozy Cottage, Charming and Bright Cottage with Salt Water Pool, A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve, Southold Cottage w/ Patio & Grill - Walk to Beach!, Town walking distance-Bridgehampton Cottage, Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays, 70 Year old cottage on 2.8 acres, stunning views and sunsets, Location and views! Located directly on Shinnecock Bay!, Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round