Summer after summer, the hills roll, the marshes rustle and the waves lap the crescent beaches. The hospitality scene is similarly constant: a dozen or so bed-and-breakfasts, and six small hotels.
Here's a rundown of Shelter Island's hotels. Be forewarned that in most cases, hotels require a two- or three-day minimum stay, and rates may vary depending on the month or day of the week.
Since it was built in 1872 as a retreat for Methodists, The Chequit (23 Grand Ave., 631-749-0018, thechequit.com) has occupied the high ground in Shelter Island Heights, the island's "downtown." Salt Hotels, which operates two boutique inns in Provincetown, Massachusetts has owned The Chequit since 2015. The design is sleek without sacrificing any rustic, seaside charm and all the rooms have modern baths and luxuriously appointed beds.
Highlights of The Chequit on Shelter Island: Adjacent to restaurants, shops and the Shelter Island Heights Pharmacy (an old-fashioned drugstore-luncheonette), the Chequit is the only hotel on the island that's within walking distance of anything else. No TVs in the rooms, but iPads with streaming services are complimentary.
The hotel's restaurant, Red Maple serving a seasonally inspired New American menu in a minimalist rustic atmosphere. The grab-and-go White Hill Café sells sandwiches, baked goods and espresso. Breakfast is a continental buffet for hotel guests.
The Chequit features a 12,120-square foot main building with 19 rooms, a restaurant and porch offering water views. The "Cottage House," at 5,406 square feet, includes 11 rooms and the 1,200-square foot "Summer House" offers six rooms. Rates per night are $275 to $895.
Shelter Island House
Shelter Island House (11 Stearns Point Rd.; 631-749-1633, shelterislandhouse.com)
The wooded property is owned by sisters Suzanne Walsh and Janet Rogler, who have summered on the island since they were children. "We wanted to recreate the Shelter Island experience we had when we were kids," Walsh said. The inn is upscale with some Euro flair (check out the pétanque courts in the front yard), with decor that falls under "beachy-chic."
Highlights of the Shelter Island House: Shelter Island House excels in outdoor seating -- there's always another porch, patio or deck around the corner as well as a pool, and those petanque courts. Bicycles are available. TVs in all rooms.
The Shelter Island House inn has 10 rooms, ranging from $275 to $595 per night. The "Osprey suite," with three bedrooms, two baths and a full kitchen is $1,900 per two nights. Open year round.
Pridwin Resort Hotel
Year after year, families return to the Pridwin Resort Hotel (81 Shore Rd., 631-749-0476, pridwin.com) spend their summer vacations on Shelter Island in classic fashion. The almost-century-old beachfront hotel overlooking Peconic Bay has been owned by the Petry family since 1962, and they've made very few changes. In fact, said their son Glenn Petry, recent redesigns have reclaimed the property's midcentury splendor from some ill-advised decorative missteps in the 1970s.
Highlights at Pridwin Resort Hotel: Kids and active adults have plenty to do at the Pridwin: there's a large pool and a private beach, three tennis courts, kayaks and paddleboards to rent. During dinner, kids can watch movies in a supervised room while parents dine in peace. TVs in all rooms.
The Pridwin's dining room is open for breakfast, lunch and dinner. The huge waterfront deck offers one of Shelter Island's best views. The menu is American and features fish caught by the owners themselves. Breakfast, lunch and dinner are served in the restaurant. Wednesday night there's an all-you-can-eat cookout.
The Pridwin Resort Hotel consists of 40 rooms and nine cottages; prices range from $275 to $385 per night. Open until Oct. 14.
The Ram's Head Inn
Cut off as Shelter Island is from the rest of Long Island, the Ram's Head Inn (108 Ram Island Dr., 631-749-0811, theramsheadinn.com) is even more remote. The lush outcropping is connected to the rest of Shelter Island by a narrow causeway. There, among the handful of luxurious dwellings, is the Ram's Head Inn, which overlooks Coecles Harbor and Gardiners Bay. The gracious 90-year-old inn has a classic Hamptons look -- cedar shake exterior, antique-accented decor.
Highlights of The Ram's Head: There may be no more serene spot on the island than the lawn, strewn with Adirondack chairs, that gently slopes down to the inn's 800-foot private beach. Sailboats, paddle boards, kayaking are available for guests' use (or moor your own boat) as is a tennis court / basketball court. TVs in common rooms.
The restaurant, whose executive chef is Joseph Smith, serves a New American menu with upscale flair (including Crescent Farm Long Island duck breast and local oysters on the half shell.) Lunch and dinner are served, as is Sunday brunch. (Guests receive a complimentary buffet continental breakfast from 8 a.m.-10 a.m.)
The Ram's Head has 17 rooms. Rooms on the weekends with shared bathrooms are $175 per night; rooms with private bathrooms, $315 per night; two-bedroom suites, $400 per night. Prices lower on weeknights. Open April through October.
Sunset Beach Hotel
When seated in one of the rattan chairs at the seaside restaurant of the Sunset Beach Hotel (35 Shore Rd., 631-749-2001, sunsetbeachli.com), you may momentarily think you're in France. The menu, the decor and the vibe -- not to mention the accents of many of the employees and guests -- are strikingly Gallic. The hotel was opened in 1997 by hotelier-to-the-stars André Balazs (Hollywood's Chateau Marmont, Chiltern Firehouse in London and Manhattan's The Mercer) and it brought a previously unknown European chic to staid Shelter Island. A restaurant, bar, rooftop lounge and a small boutique hug the shoreline; the rooms are housed in a separate building; each has a private deck with water views. Nudity is allowed.
Highlights of Sunset Beach Hotel: As befits the crowd, accommodations here feature luxe linens and flat-screen TVs with DVDs. Crescent Beach is right at your door, and there are complimentary bikes and paddleboards.
The restaurant specializes in the coastal cuisines of France and Italy (rack of lamb with provençal vegetables, casareccia pasta with shrimp, asparagus, orange-fennel butter and Sunset Bouillabaisse). Breakfast, lunch and dinner are served.
Sunset Beach Hotel rates for the 20 rooms differ from month to month; in July they range from $ 525 to $545 per night and can rise to more than $660 in August and September. Open through Sept. 2.
The Dering Harbor Inn
The Dering Harbor Inn (13 Winthrop Rd., 631-749-0900, deringharborinn.net) isn't really an inn but a collection of 20 privately owned apartments perched on a bluff overlooking Dering Harbor. In the rental program, two modest studios are located in a main building that also houses a yoga studio and fitness room. One two-bedroom suite and 15 one-bedroom suites most of which are either on the water or face it are also available. Each property has been furnished by its owner; photos are available on the website.
Highlights of the Dering Harbor Inn on Shelter Island: A great place for kids (children under 12 stay free), the complex has a large pool and plenty of green space for running around. Guests have free access to the yoga studio and gym; access to the tennis courts (or lessons) are extra. No pets allowed.
At the Dering Harbor Inn, the four studios are $360 per night; one-bedroom suites are $425 to $455 per night; two-bedroom villas are $600 to $655 per night. Open through Oct. 20.
Shelter Island information
Shelter Island is only accessible by ferry. The North Ferry (631-749-0139, northferry.com) connects to Greenport on the North Fork. Rates are $16 same-day round-trip, $11 one way. The South Ferry (631-749-1200, southferry.com) connects to North Haven on the South Fork. Rates are $17 same-day round-trip, $14 one way.
On the island, car service is available from Shelter Island Go-Fors (631-749-4252). Bikes can be rented from Piccozzi's Bike Shop (177 N. Ferry Rd.; 631-749-0045, jwpiccozzi.com).