A pebbled beach with a sunset and a distant bridge.

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Check availability on Shelter Island Heights Beach Hotel

Our top choices for Shelter Island Heights beach hotels

Cribs (free), rollaway beds (surcharge), WiFi (free), bed sheets

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (321 reviews)
The price is CA $125
CA $144 total
includes taxes & fees
Jul 20 - Jul 21
Clinton Motel
Exterior

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1,000 reviews)
The price is CA $129
CA $148 total
includes taxes & fees
Jul 19 - Jul 20
Pier Blue Inn Old Saybrook - Essex
Exterior

Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (244 reviews)
The price is CA $111
CA $128 total
includes taxes & fees
Jul 19 - Jul 20
Lamplighter Motel - Clinton, Connecticut
Outdoor dining

The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (39 reviews)
The price is CA $532
CA $607 total
includes taxes & fees
Aug 11 - Aug 12
The Chequit
Private beach, sun loungers, beach umbrellas, beach towels

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (93 reviews)
  • cleanliness
    Unwind on a private sandy shoreline with loungers and umbrellas at this bayside retreat, where ocean-view dining meets coastal tranquility.
The price is CA $995
CA $1,251 total
includes taxes & fees
Aug 16 - Aug 17
The Pridwin Hotel
Beach nearby

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (42 reviews)
The price is CA $440
CA $503 total
includes taxes & fees
Jul 27 - Jul 28
West Neck Guesthouse
Front of property - evening/night

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (60 reviews)
The price is CA $444
CA $507 total
includes taxes & fees
Jul 30 - Jul 31
Shelter Island House
Deluxe Double Room, 1 King Bed, City View

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
2.0 star property
Hampton Bays
7.4 out of 10, Good, (93 reviews)
The price is CA $222
CA $254 total
includes taxes & fees
Jul 20 - Jul 21
Hampton Bays Hotel on Main
Beach nearby, white sand, beach towels

The Penny Lane

The Penny Lane
3.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (87 reviews)
The price is CA $320
CA $366 total
includes taxes & fees
Aug 11 - Aug 12
The Penny Lane
Exterior

Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (354 reviews)
The price is CA $398
CA $455 total
includes taxes & fees
Aug 16 - Aug 17
Zey Hotel
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.
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Choose what matters most at beach hotels in Shelter Island Heights

Pool
Breakfast included

Find out more about Shelter Island Heights

Shelter Island Heights and its attractions for beach lovers

For beach-loving travellers, Shelter Island Heights is a hidden gem offering a harmonious blend of relaxation and adventure. Start your day at Crescent Beach, a picturesque stretch perfect for sunbathing and swimming, where children can safely play in the gentle waves. Just a short stroll away, you can explore the serene grounds of the Shelter Island Historical Society, which hosts art exhibits and provides insights into the island’s charming past. For a touch of nature, head to the Mashomack Preserve, where you can hike scenic trails that lead to breathtaking views of the surrounding waters—an excellent spot for family picnics. After a day of exploration, unwind at Sunset Beach, renowned for its stunning sunset views and laid-back atmosphere, where you can sip on cocktails while your kids build sandcastles. The area boasts several quality hotels, such as The Chequit, blending modern comforts with a quaint, coastal aesthetic, ensuring your family enjoys attentive service and luxurious amenities. Staying here not only puts you within walking distance of these attractions but also allows you to immerse yourself in the local charm, making for an unforgettable beach getaway.

Find the best beach hotels and resorts in Shelter Island Heights

For those seeking a seaside escape in Shelter Island Heights, these hotels offer the perfect blend of beach access and comfortable amenities. Each hotel is designed to enhance your beach getaway experience.

The Pridwin Hotel

  • Why it's great for the ultimate beach vacation spot: The Pridwin Hotel is an exquisite choice for beach enthusiasts, offering unparalleled access to a private sandy beach. With an impressive guest review rating of 9.6, guests can indulge in ocean views and exclusive beach amenities including sun loungers and umbrellas for ultimate relaxation. The hotel also features an ocean-view restaurant, allowing guests to dine while soaking in the stunning surroundings.
  • Other amenities: In addition to its prime beach location, The Pridwin Hotel boasts a range of luxurious facilities including a spa with hydrotherapy treatments, a pool with sun loungers, and a fitness centre. Guests can unwind on the terrace or enjoy complimentary breakfast daily. The hotel also offers activities like billiards and has a concierge service to assist with local excursions, ensuring a memorable stay for all travelers.
  • Nearby attractions: Crescent Beach - 0.1 km, Sunset Beach - 0.9 km, Shelter Island Whale's Tail - 4 km

House on Chase Creek

  • Why it's great for the ultimate beach vacation spot: The House on Chase Creek is a charming and affordable retreat for those looking to enjoy the beach. With a solid review rating of 9.4, this hotel is just a short distance from nearby sandy beaches, making it a convenient option for beach lovers. Guests can enjoy a relaxed atmosphere with access to a terrace and a patio, perfect for soaking up the sun.
  • Other amenities: This quaint guesthouse offers complimentary toiletries and features a fireplace for cozy evenings. Guests will appreciate the self-parking options and air conditioning for comfort. For those keen on golfing, nearby courses provide excellent recreational opportunities, making it an ideal spot for a beach and golf getaway.
  • Neighborhood: The Heights
  • Nearby attractions: Crescent Beach - 2.1 km, Sunset Beach - 1.9 km, Shelter Island Country Club - 0.9 km

The Chequit

  • Why it's great for the ultimate beach vacation spot: The Chequit is a stylish hotel that appeals to beach lovers with its close nearby the shoreline, receiving an excellent guest review rating of 8.8. This charming hotel offers a relaxed atmosphere with beautifully decorated rooms and easy access to nearby beaches, making it an inviting choice for those looking to soak up the sun and surf.
  • Other amenities: Guests will appreciate the premium bedding and access to self-parking. The hotel features a delightful garden area for relaxation and is known for its welcoming service. While it may not have direct beach amenities, the nearby beach is just a short stroll away, allowing travelers to enjoy the coastal experience without compromise.
  • Neighborhood: The Heights
  • Nearby attractions: Crescent Beach - 2.2 km, Sunset Beach - 1.8 km, Shelter Island Country Club - 0.9 km

Shelter Island House

  • Why it's great for the ultimate beach vacation spot: Shelter Island House is a delightful mid-range option for beachgoers, a review rating of 8.4. Located conveniently near the beach, this hotel provides a comfortable stay with the added bonus of a free breakfast. Guests can enjoy easy access to the sandy shoreline while also having a relaxing space to unwind after a day in the sun.
  • Other amenities: The hotel features a terrace and a garden, allowing guests to embrace the outdoors. Sheltered from the hustle and bustle, travelers can enjoy complimentary toiletries and air conditioning for a refreshing retreat. With options for dining and a concierge service, this hotel ensures that guests have everything they need for a memorable beach holiday.
  • Nearby attractions: Crescent Beach - 0.8 km, Sunset Beach - 0.6 km, Shelter Island Whale's Tail - 2.7 km

West Neck Guesthouse

  • Why it's great for the ultimate beach vacation spot: West Neck Guesthouse is a cozy option for those seeking a beach getaway, reflected in its review rating of 8.2. Conveniently located near the beach, this guesthouse provides a comfortable atmosphere with essential amenities for a relaxed stay, including a complimentary breakfast to start the day off right.
  • Other amenities: Guests can enjoy accessible parking and a kitchenette for added convenience. The hotel also features air conditioning, a lovely garden, and daily housekeeping to ensure a comfortable experience. With its commitment to guest comfort and access to nearby beach activities, West Neck Guesthouse is a great choice for beach travelers.
  • Nearby attractions: Crescent Beach - 1.1 km, Sunset Beach - 0.9 km, Shelter Island Whale's Tail - 2.2 km

Top Shelter Island Heights Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Love the Dolce Cabana beach area, store and upstairs bar area!"
Marco LaMonte 2-night trip
Posted 20 hours ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

What are the best beach hotels in Shelter Island Heights?
For top-rated beach hotels in Shelter Island Heights, consider The Pridwin Hotel, The Chequit, and The Rams Head Inn.

The 4-star Pridwin Hotel, with a 9.6 rating, offers a private beach on site and many rooms feature ocean views. Guests frequently comment on the beautiful, clean rooms and delicious food.

The Chequit, a 3-star hotel rated 9.0, is located very near a beach and provides free self-parking. Reviewers often mention its comfortable premium bedding.

The 4-star Rams Head Inn, with a 7.6 rating, boasts a private beach for its guests and provides complimentary continental breakfast. It also features dining options specifically for couples.
How much does a beach hotel in Shelter Island Heights cost?
Prices for beach hotels in Shelter Island Heights vary, but you can find a great deal from CA $128 on Expedia. You're likely to find lower rates if you're travelling during the off-peak season or mid-week. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.
Which Shelter Island Heights hotels are near the best beaches?
For hotels near the best beaches in Shelter Island Heights, consider The Pridwin Hotel, The Chequit, or The Rams Head Inn.

The 4-star Pridwin Hotel, with a 9.6 rating, offers a private beach on site, with many rooms providing partial or full ocean views. Guests frequently comment on the beautiful, clean rooms and the amazing amenities.

The Chequit, a 3-star hotel with a 9.0 rating, is located near the beach. It offers free self-parking and free WiFi, and even allows pets to stay free.

For a private beach experience, the 4-star Rams Head Inn (7.6 rating) also has a private beach on site. This hotel is also noted for its continental breakfast, which is free for guests.
Which beach hotels in Shelter Island Heights are good for families?
For families seeking a beach hotel in Shelter Island Heights, The Pridwin Hotel stands out.

The 4-star Pridwin Hotel, with a 9.6 rating, offers a private beach, allowing for easy access and a dedicated space for family enjoyment. Many rooms feature partial or full ocean views, and the hotel provides complimentary continental breakfast. Guests frequently comment on the beautiful, clean rooms and great facilities.
What are the best Shelter Island Heights hotels with ocean views?
For hotels in Shelter Island Heights with ocean views, The Pridwin Hotel is a top recommendation.

The Pridwin Hotel, a 4-star property with an impressive 9.6 rating, offers a variety of views including partial ocean, full ocean, partial sea, and general water views. Guests frequently praise its excellent facilities and delicious food, and it provides complimentary continental breakfast.
What are the top-rated beach hotels in Shelter Island Heights with a pool?
The Pridwin Hotel is a top-rated beach hotel in Shelter Island Heights that features a pool.

The 4-star Pridwin Hotel, with a 9.6 rating, offers a private beach location and many rooms provide partial or full ocean views. Guests can also enjoy the seasonal outdoor pool and a complimentary continental breakfast. Reviewers frequently highlight the beautiful and clean rooms, amazing amenities, and delicious food.
Which beach hotels in Shelter Island Heights are good for couples?
For couples looking for a beach hotel in Shelter Island Heights, The Rams Head Inn is a good option.

The Rams Head Inn, a 4-star property with a 7.6 rating, offers a private beach area, which can be ideal for a romantic and secluded experience. Couples often appreciate the included breakfast options, with both continental and full breakfast provided free of charge.
Which area of Shelter Island Heights is best to stay in for beaches?
The best area to stay in Shelter Island Heights for beaches is the northern coast, particularly around Crescent Beach, also known as Wades Beach.

This area is renowned for its easy access to the water and its generally calm, family-friendly environment. Crescent Beach is a long stretch of sand ideal for swimming and sunbathing, and it's well-equipped with amenities like restrooms and picnic areas. The roads here, such as Crescent Beach Road, often have direct pathways to the shoreline.

Families will find this area particularly appealing due to the shallow, gentle waters at Crescent Beach, which are great for children. There are also several accommodation options here that cater to families, offering activities and facilities aimed at a relaxing beach holiday.

For couples looking for a tranquil beach escape, the northern coast also offers a nice setting. You can enjoy quiet walks along the shore, watch the sunset over the water, and find restaurants with lovely views.
What is the best time of year to stay in a beach hotel in Shelter Island Heights?
The most popular time to stay in a beach hotel in Shelter Island Heights is during July and August. These months boast the warmest weather, with average temperatures hovering around 25°C, creating ideal conditions for enjoying the island's beautiful beaches and water activities.

During this peak season, the island truly comes alive, with all beach facilities, water sports rentals, and outdoor dining options fully operational and buzzing with activity. It's a wonderful time for families looking for a classic summer getaway, as the warm waters are superb for swimming and building sandcastles. You'll find a lively, yet relaxed, atmosphere, superb for making lasting holiday memories.

For those seeking a slightly more tranquil experience with excellent weather, June offers a fantastic alternative. While still warm and sunny, with temperatures often reaching the low 20s, it's before the absolute peak of the summer. You may find better value on hotel stays and it can be easier to secure reservations at the island's most sought-after restaurants.
How can I save on a beach hotel in Shelter Island Heights with Expedia?
With Expedia, you'll unlock our lowest prices by becoming a One Key™ member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Shelter Island Heights beach hotels. Typically, booking in advance will help you save on your hotel. If you're feeling spontaneous, check out the last-minute deals.
What beach activities should we do in Shelter Island Heights?
The best beach activities in Shelter Island Heights revolve around its serene waters and picturesque shorelines, with kayaking, paddleboarding, and relaxing on the sand being top choices.

For those who enjoy being on the water, kayaking and paddleboarding offer a fantastic way to explore the calm bays and inlets surrounding Shelter Island. You can rent equipment from local outfitters, often located near the main ferry landings or in the Heights area itself. These activities are particularly good for couples looking for a peaceful way to spend an afternoon together, allowing them to discover hidden coves and enjoy the natural beauty of the island from a unique perspective.

Families will find the beaches in Shelter Island Heights ideal for a relaxing day out. Crescent Beach, for instance, is well-known for its gentle waves and soft sand, making it superb for children to play and swim. There are also designated areas for picnicking, and the beach offers lovely views of the surrounding waters.
Is it cheaper to book flights and a beach hotel in Shelter Island Heights as a package?
Booking a beach hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking a beach vacation package well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.
Can I cancel my beach hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right beach hotel in Shelter Island Heights for you.

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