Shelter Island accommodations — from gracious waterfront inns to elegant guesthouses, to sumptuous B&Bs — are ready for the summer with special measures for the safety of guests and staff.
Please note, all locations are following best practices in response to the pandemic; some amenities may not be fully accessible at this time due to continued restrictions.
Here is a selection of places to stay while visiting Shelter Island. When booking any property, deal directly with the establishments to get the best rates.
1. Dering Harbor Inn
A tranquil harborside retreat, built in the mid-60s the Dering Harbor Inn offers waterfront villas and suites, one-bedroom water view suites, and king and queen hotel suites.
The 1960s architecture is featured notably on the Inn’s beautiful mahogany doors. The Inn turned into a private co-op in 1981 under the name Winthrop Manor for the road that it’s located on.
The Inn is a short walk from the town’s shops and restaurants as well as the North Ferry terminal for easy access to transportation. With rates for every budget, accommodations offer waterfront access, daily osprey aerial displays, and breathtaking sunset views. Long-term guests will enjoy the best deals, and there are even a couple of units for sale.
As more COVID-19 restrictions are lifted, fabulous amenities across the child-friendly property are becoming available such as the fitness center, tennis courts, heated pool, deep water dock, and a juice bar/cafe.
The Inn is open seasonally and co-op properties are open year-round. For more information about sales, call the main office.
13 Winthrop Road | 631- 749-0900 | deringharborinn.net
2. The Ram’s Head Inn
Built in 1929, The Ram’s Head Inn is a Shelter Island gem with world-class hospitality, accommodations, and fine dining. It retains old-fashioned seaside charm but has been kept up to date by owners Linda and James Eklund now cruising into their 37th year of operating the Inn.
“The whole property has been readjusted to ensure social distancing,” Linda Eklund said in a phone conversation with the Gazette. For example, the corn hole and bocce equipment are UV sanitized. The staff has delineated squares on the lawn for the use of guests and their families.
Guests also enjoy exclusive use of a private beach, kayaks, tennis, and on-site dining, with live music on Tuesdays, Thursdays, and Sundays.
“Phase Two was a big thing, it had been a very long time, bringing in staff and focusing on the guests has been really nice,” Linda said. The inn has lost all its summer weddings through cancellations or postponements to the fall of 2021. “Without the weddings, we will focus on regular guests and really enjoy a quieter time.”
108 South Ram Island Drive | 631-749-0811 | theramsheadinn.com
3. SEVEN on Shelter
Mornings start with a to-go style Beach Breakfast Basket filled with fresh fruit, granola, creamy yogurt, artisanal cheese, local hard-boiled organic eggs, freshly baked chocolate croissants, and baguettes with gourmet jams.
The newly restored 1902 farmhouse is a 21st-century bed-and-breakfast that provides guests with a low-key hideaway while offering all the luxuries a modern globetrotter needs.
Amenities include sustainable toiletries, walk-in tile showers, flat-screen TVs, and quality beds topped with goose-down comforters. Plus, there are bicycles to let, yard games to play, and a fire pit to enjoy on cool evenings. The inn features contemporary art and kinetic sculptures throughout the property.
Long term stays are encouraged at SEVEN, which is registered with the Town of Shelter Island, Rental Registration #19W-0007.
Contact SEVEN directly for the best rate, and to organize flowers, wine, champagne, or chocolate-covered strawberries for your guest room to make your stay extra special. SEVEN is dog friendly, upon request.
7 Stearns Point Road | 347-326-3259 | sevenonshelter.com
4. Candlelite Inn and Guest Cottages
This beautiful Victorian Inn, conveniently located in the center of Shelter Island, features a wrap-around porch and deep, shady lawn. The Candlelite Inn has five guest rooms with private baths, central AC, high-speed Wi-Fi, and continental breakfast.
Guests looking for additional privacy can check out the Honeymoon Cottage. The 350 square foot cottage features antique furniture, a private entrance, king sleigh bed, a six-foot double whirlpool, a spacious shower, television, and AC. A minimum two-night stay is required. Cottages are available for those considering a long-term stay.
The Candlelite Inn is walking distance from a several shops and restaurants, farm stands, the local weekly farmer’s market, and the idyllic 2,039-acre Mashomack Preserve. With advance notice and extra charge, the Inn can also schedule hair services available in JBS, the on-premise salon, which features hair design and styling, highlighting, and color. This property does not accommodate children or pets.
3 South Ferry Road | 631-749-0676 | thecandleliteinn.com
5. Shelter Island House
Shelter Island House offers a luxurious stay with opulent accommodations. Built in the 1800s, the inn has been reinvented with distinction, warmth, and intimacy. Guests can enjoy architectural historic details and chic elegance. Owners and sisters Suzanne Walsh and Janet Rogler offer hospitality for those looking to escape in style, close to the beach.
Amenities include luxurious gardens, on-site pool, petanque courts, free bicycles, and a restaurant and bar. The hotel has eight guest rooms all with modern updated private baths plus a three-bedroom suite with a wrap-around porch and private entrance.
The sisters own a second property just a short walk away called West Neck Guesthouse (see the next slide for details).
11 Stearns Point Road | 631-749-1633 | shelterislandhouse.com
6. West Neck Guesthouse
A sister property to Shelter Island House, this former private residence has been converted to an intimate guest house conveniently located within walking distance to Crescent Beach, shops, restaurants, and activities. Each room offers a unique sweetness with luxurious king-size beds, private baths, and chic furnishings.
West Neck Guesthouse shares amenities with Shelter Island House and has its own relaxing private garden area and petanque courts.
31 West Neck Road | 631-599-3430 | westneckhouse.com
7. Two South Ferry
This renovated 1930s farmhouse gives a flavor of Shelter Island local hospitality to make you feel at home. Open year-round, all rooms offer free Wi-Fi, private baths, and AC. The location in the center of the Island makes for ease of activities. Each of the four guest rooms has its own wing with a private deck. They open onto a common room where an extended Continental breakfast is offered.
“It is what it is, we have had a few reservations and a few calls,” owner Chrissy Edwards told the Gazette. The B&B is not booking back-to-back stays and is not providing daily chamber maid service in an effort to keep guests and staff safe.
2 South Ferry Road | 631-749-3208 | twosouthferrybandb.com
8. House On Chase Creek
House on Chase Creek is your getaway in the heart of Shelter Island Heights. This B&B offers classic charm and antiques plus all the modern amenities and conveniences. Open year-round with just four rooms, guests can enjoy quiet relaxation with a beautiful view of Chase Creek. Set amid the charming homes, shops, and restaurants of the Shelter Island Heights Historic District, the house is within walking distance of the North Ferry, and so to Greenport, and its train and bus connections to New York City.
“The coronavirus has been the best thing to happen to me for my business in years, mostly because so many other hotel properties and Airbnbs on Shelter Island are closed, so new guests are finding me and loving it,” said owner Bill Cummings in a recent phone call with the Gazette.
3 Locust Ave | 631-559-2296 | chasecreek.com
