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Top 10 Shelter Island hotels and places to stay

Our top choices for Shelter Island hotels

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1013)
"Excellent Stay"
The price is £84
includes taxes & fees
15 Sept - 16 Sept
Quality Inn Old Saybrook - Westbrook

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (269)
"Great stay. Fantastic location. Wonderful motel providing everything you need. Clean, comfortable and excellent value."
The price is £67
includes taxes & fees
1 Sept - 2 Sept
Clinton Motel

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.8 out of 10, Good, (1014)
"Good budget friendly hotel"
The price is £68
includes taxes & fees
1 Sept - 2 Sept
Pier Blue Inn Old Saybrook - Essex

Liberty Inn

2.0 star property
7.4 out of 10, Good, (623)
"Service at front desk was very good!"
The price is £63
includes taxes & fees
2 Sept - 3 Sept
Liberty Inn

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
7.2 out of 10, Good, (445)
"Definitely an older property, but staff were helpful people and our room was clean and quiet. Easy car ride to get to the ocean."
The price is £65
includes taxes & fees
10 Sept - 11 Sept
Econo Lodge Inn & Suites Old Saybrook Westbrook

Shorewood Inn

2.5 star property
8.6 out of 10, Excellent, (676)
"Good place to stay"
Shorewood Inn

Super 8 by Wyndham Old Saybrook

2.0 star property
7.0 out of 10, Good, (896)
"It was clean and quiet"
The price is £69
includes taxes & fees
15 Sept - 16 Sept
Super 8 by Wyndham Old Saybrook

Greenporter Hotel

2.0 star property
9.4 out of 10, Exceptional, (196)
"Close to town and pool was great!"
Greenporter Hotel

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (74)
"Awesome all around! Staff was super nice "
The Pridwin Hotel

Hampton Bays Hotel on Main

2.0 star property
6.8 out of 10, (55)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
Hampton Bays Hotel on Main

Southampton Long Island Hotel

2.5 star property
8.6 out of 10, Excellent, (198)
"Good location. Nice people!! "
The price is £155
includes taxes & fees
1 Sept - 2 Sept
Southampton Long Island Hotel

Lamplighter Motel - Clinton, Connecticut

2.5 star property
6.2 out of 10, (214)
"Would stay again. "
The price is £59
includes taxes & fees
7 Sept - 8 Sept
Lamplighter Motel - Clinton, Connecticut

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (324)
"Great place!"
The price is £211
includes taxes & fees
29 Sept - 30 Sept
The Bentley Hotel Southampton

Hamlet Inn

2.0 star property
8.4 out of 10, Very good, (418)
"Very accommodating friendly people! "
The price is £150
includes taxes & fees
1 Sept - 2 Sept
Hamlet Inn

The Niantic Inn

2.0 star property
9.2 out of 10, Wonderful, (104)
"Enjoyed my stay"
The price is £139
includes taxes & fees
4 Sept - 5 Sept
The Niantic Inn

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (244)
"Everything was fantastic, will stay again!"
The Captain Stannard

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (160)
"Charming, beautiful inn; excellent food and service."
The price is £179
includes taxes & fees
23 Sept - 24 Sept
Westbrook Inn B&B

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (187)
"Nice place to stay out on the east end"
Ocean Vista Resort

Aqualina Inn Montauk

2.5 star property
9.6 out of 10, Exceptional, (472)
"The room was very clean and the staff accommodating ! "
The price is £121
includes taxes & fees
29 Sept - 30 Sept
Aqualina Inn Montauk

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (504)
"Had a fantastic room 324 in the newer building.. Breakfast was delicious and service terrific.."
The price is £238
includes taxes & fees
1 Sept - 2 Sept
Copper Beech Inn
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Where to stay in Shelter Island

Find the best Shelter Island areas for the activities you enjoy most. Learn more about Shelter Island
Learn more about Shelter Island

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Wades Beach and Sunset Beach.

Coecles Harbor

While Coecles Harbor isn't home to many top sights, Shelter Island Whale's Tail and Gardiner's Bay Country Club are some notable places to visit nearby.

Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Shorewood

While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wades Beach and Sunset Beach.

Accommodation near Shelter Island attractions

Gardiner's Bay Country Club

Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

Learn more about Shelter Island

Escape to Shelter Island! Enjoy its island views, natural setting and beaches.

Photo by tom owens
Open Photo by tom owens

Top Shelter Island Hotel Reviews

More cheap stays in Shelter Island

More cheap stays in Shelter Island

Find out more about Shelter Island

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Scenic Beaches: Shelter Island boasts stunning beaches, perfect for relaxation and sunbathing.
  • Outdoor Adventures: Enjoy activities like golfing, hiking, and water sports amidst picturesque landscapes.
  • Rich History: Explore historic buildings and local culture that add charm to the island.
  • Wine Tastings: Indulge in delightful wine tastings, showcasing the region's unique flavours.
  • Unique Accommodation: Choose from charming B&Bs to family-friendly resorts for a memorable stay.

Find great hotels near Shelter Island

Whether you seek a charming bed and breakfast for a cosy retreat or an agritourism property for a unique experience, Shelter Island offers a delightful selection of accommodation options. From pet-friendly hotels to family-friendly resorts, you'll discover the perfect base for your adventure. Explore classic Shelter Island hotels that blend comfort with local character, ensuring a memorable stay in this picturesque destination.

  • Sound View Greenport: Experience the perfect blend of beachside leisure and business convenience at Sound View Greenport. Located a mere 2.5km from Shelter Island, this 3.5-star hotel caters to both holidaymakers and business travellers alike. The hotel boasts direct access to the beach, ideal for sun-seekers and those wishing to unwind by the sea. Business amenities such as meeting rooms and conference spaces make it an excellent choice for corporate retreats. Additionally, the hotel is pet-friendly, welcoming dogs and cats, ensuring that your furry companions can join in on the adventure.
  • The Harbor Front Inn: Situated just 1.9km from Shelter Island, The Harbor Front Inn offers a charming retreat for both leisure and business guests. This 3.5-star accommodation combines a pet-friendly atmosphere with essential business facilities, making it a versatile choice for all types of visitors. The hotel's amenities include in-room pet allowances and services for business travellers, ensuring a comfortable stay for everyone. Enjoy picturesque views and easy access to local attractions while relishing the relaxed coastal vibe of this delightful inn.
  • Sag Harbor Inn: Nestled 3.1km from Shelter Island, Sag Harbor Inn is a distinguished 3.5-star hotel ideal for business travellers seeking a serene escape. The inn offers essential amenities including meeting rooms, perfect for hosting corporate gatherings or conferences. Set in a tranquil location, it allows guests to unwind after a busy day while still being close to the vibrant local culture. With its emphasis on providing a professional yet comfortable environment, Sag Harbor Inn is an excellent choice for those seeking both productivity and relaxation.

Where to stay near Shelter Island

Discover the charm of Shelter Island, a picturesque destination perfect for outdoor adventures, romantic getaways, and beach relaxation. This tranquil locale offers a unique blend of scenic beauty and historical allure, making it an ideal spot for family-friendly excursions. Venture into nearby Long Island for more budget-friendly options and vibrant atmospheres, ensuring a memorable stay in this lovely part of the United States.

  • Hamptons: Situated 5.6km from Shelter Island, the Hamptons are renowned for their picturesque beaches and upscale charm. This area is a seasonal hotspot, particularly vibrant from May through August. Visitors flock here for romantic getaways, outdoor activities, and a laid-back beach experience. Notable attractions include pristine family-friendly beaches, scenic lakes, and renowned golf courses. The local music scene often features concerts, and numerous resorts provide luxurious accommodations. The Hamptons embody a quintessential coastal escape, making it a must-visit during your stay.
  • Greenport: Just 1.9km from Shelter Island, Greenport is a charming village that draws visitors year-round, peaking in the summer months of June to August. Known for its romantic aura and outdoor adventures, this quaint locality offers beautiful beaches and a variety of events throughout the year. The vibrant waterfront is perfect for leisurely strolls, while local golf courses and music concerts provide ample entertainment. Greenport is also home to notable event venues, making it an ideal spot for both relaxation and recreation.
  • Sag Harbor: Located 3.1km from Shelter Island, Sag Harbor is a historic whaling village that offers a unique blend of culture and coastal beauty. The area experiences moderate seasonal tourism, with the peak influx during the summer months. Visitors come for its outdoor activities, stunning beaches, and romantic ambience. The town boasts picturesque parks, family-friendly beaches, and local golf courses. With its charming streets lined with boutiques and eateries, Sag Harbor is a delightful destination for those looking to unwind and explore.

Things to do in and around Shelter Island

Discover the charm of Shelter Island, perfect for outdoor and romantic getaways. Enjoy activities such as golfing and skiing, while indulging in delightful wine tastings and exploring the island's picturesque landscapes. Whether you're lounging on the beach or immersing yourself in local attractions, Shelter Island offers a unique blend of relaxation and adventure for every visitor.

Shopping

For a delightful shopping experience, visit the Greenport Farmers' Market, only 1.9km away, for local produce and artisan goods. The Style Bar is a charming store just 3.1km away, offering stylish finds. If you're up for a drive, Victoria's Secret is 5.6km away for quality lingerie.

Recreation

Shelter Island Whale's Tail offers a fun mini-golf experience, perfect for families and adventure seekers. For relaxation, visit Cedar Point County Park, where you can unwind in nature’s embrace. Noyac Golf Club provides an outdoor sports atmosphere, ideal for enjoying a round of golf amidst stunning scenery.

Adventure

Experience the thrill at Splish Splash Water Park, located 14.3km from Shelter Island, offering exhilarating water rides. For aerial adventure, the Long Island Skydiving Center, 16.8km away, promises an unforgettable skydiving experience. Alternatively, enjoy the stunning scenery along the Walking Dunes Trailhead, 9.9km from the island.

Nightlife

Experience the whimsical Greenport Carousel, just 1.9km away, perfect for family fun. For a cultural evening, visit the Bay Street Theatre, 3.1km out, offering a blend of entertainment and romance. Catch a film at Regal UA East Hampton, 6.8km away, ideal for a cosy night out.

Booking tips and Expedia advantages for Shelter Island

To save money on your trip to Shelter Island, consider visiting between January and March when hotel prices are at their lowest. Tuesday is the cheapest day to stay, while Saturdays tend to be pricier. Use Expedia to find eco-friendly accommodations and filter options by price to secure the best deals. Additionally, combine your hotel, flights, and activities for potential savings. To explore the area, utilise affordable public transport or enjoy free activities such as walking along the beach or visiting local parks.

  • The most and least expensive months on average to stay in a hotel: The hotel pricing in Shelter Island is moderately seasonal. The cheapest months to stay in Shelter Island are January to March, where the prices are moderately lower. This is in comparison to June to August, where prices are moderately higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Shelter Island is Tuesday. The most expensive day to stay in Shelter Island is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your choices based on your budget, desired location, and the type of hotel you prefer. For instance, selecting the Eco-certified option will showcase sustainable and environmentally-friendly hotels that are currently available. To discover the best prices and offers, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially save money by combining your Shelter Island hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Shelter Island

Ideal for outdoor and romantic getaways, Shelter Island offers a delightful mix of beaches, historic buildings, and urban parks. Visitors can immerse themselves in the local culture while enjoying scenic spots like Sunset Beach. Whether you're seeking relaxation or adventure, the island caters to all, providing a perfect backdrop for a memorable holiday experience.

  • Gardiner's Bay Country Club: Enjoy a round of golf at this picturesque course, nestled within the serene landscapes of Shelter Island. With well-maintained greens and stunning views of Gardiner’s Bay, it offers a tranquil escape for both seasoned golfers and beginners alike.
  • East Hampton Main Beach: Just 7.5km away, this beautiful beach is perfect for sunbathing and swimming, offering a quintessential beach vibe. Stroll along the sandy shores or partake in water sports while enjoying the vibrant atmosphere.
  • Orient Point County Park: Located 5.0km from Shelter Island, this family-friendly park features lush greenery and outdoor activities. Ideal for picnics and leisurely strolls, it provides a refreshing urban escape amidst nature.

Best time to go to Shelter Island

The best time to visit Shelter Island is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyAverageModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageAverage
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyHighAverage
July73.0°F (22.8°C)Light RainMostly SunnyHighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyHighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageModerately High
October59.7°F (15.4°C)Light RainMostly SunnyLowAverage
November49.6°F (9.8°C)Light RainMostly SunnyLowAverage
December42.1°F (5.6°C)Light RainMostly CloudyLowModerately Low

The nearest major airports for your trip to Shelter Island

To visit Shelter Island, you have several airport options. Islip, NY (ISP-MacArthur) is 27.3km away, with nearby hotels like the 3.5-star Hyatt Regency Long Island, situated 2.5km from the airport, and Jake's 58 Casino Hotel - Adult Only, also 2.5km away. Montauk, NY (MTP) is closer at 13.7km, offering accommodations such as the 4-star Gurney's Montauk Resort & Seawater Spa, 3.1km from the airport. New Haven, CT (HVN-Tweed - New Haven Regional) is 19.9km away, with options like the Omni New Haven Hotel at Yale, located 1.9km from the airport. Each hotel provides convenient access to its respective airport.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

When is the best time to go to Shelter Island?
The most popular time to visit Shelter Island is during the summer months, particularly July. This is when the island truly comes alive with vibrant outdoor activities, charming events, and a bustling atmosphere. With average temperatures around 25°C, visitors can enjoy the warm weather while exploring the island's beautiful beaches, scenic walking trails, and delightful local shops.

During the peak season from June to August, Shelter Island attracts a diverse crowd of travellers, making it an exciting time to experience the community vibe. You'll find plenty of opportunities for outdoor adventures, whether it's kayaking in the calm waters, cycling along the picturesque paths, or simply relaxing on the sandy shores. The long, sunlit days provide ample time for sightseeing and enjoying the island's natural beauty.

For those who appreciate a quieter experience, consider visiting in September. The summer crowds begin to dwindle, yet the weather remains pleasantly warm, often still hovering around 22°C. This month also offers a wonderful opportunity to enjoy local events without the hustle and bustle of high season. You can take leisurely walks through the vineyards or indulge in fresh seafood at waterfront restaurants, all while soaking in the stunning autumnal scenery.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Shelter Island.
How can I save on a Shelter Island hotel booking with Expedia?
Before booking your Shelter Island hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia.
How much is the nightly rate at a Shelter Island hotel?
Prices for hotels in Shelter Island often vary, but you can find a great deal from £59 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.