A pebbled beach with a sunset and a distant bridge.

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Check availability on Shelter Island Heights Beach Hotel

Tonight
Aug 31 - Sep 1
Tomorrow
Sep 1 - Sep 2
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Shelter Island Heights beach hotels

Outdoor dining
Superior King
View from room
Frette Italian sheets, premium bedding, Tempur-Pedic beds

1. The Chequit

The Chequit
The Heights
CA $366
CA $418 total
includes taxes & fees
Sep 9 - Sep 10
The Chequit
Restaurant
Standard Room, 1 King Bed, Bay View | Room amenity
A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.
Exterior

2. House on Chase Creek

House on Chase Creek
The Heights
CA $342
CA $390 total
includes taxes & fees
Sep 8 - Sep 9
House on Chase Creek
Private beach, sun loungers, beach umbrellas, beach towels
Seasonal outdoor pool, pool umbrellas, sun loungers
Premium bedding, iron/ironing board, WiFi (free), individually furnished
Terrace/patio

3. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
  • Unwind on a private sandy shoreline with loungers and umbrellas at this bayside retreat, where ocean-view dining meets coastal tranquility.
CA $743
CA $934 total
includes taxes & fees
Sep 15 - Sep 16
The Pridwin Hotel
Front of property - evening/night
Bar (on property)
Property amenity
Property amenity

4. Shelter Island House

Shelter Island House
Shelter Island Heights
CA $440
CA $502 total
includes taxes & fees
Sep 1 - Sep 2
Shelter Island House
Beach nearby
Suite, 1 King Bed, Kitchenette (Living Room) | Bathroom
Free self parking
Deluxe Room, 1 King Bed

5. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
CA $436
CA $498 total
includes taxes & fees
Sep 1 - Sep 2
West Neck Guesthouse
Exterior
Private Suite, 1 King Bed, Non Smoking (Private Suite - Adults Only)
Bar (on property)
Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking

6. Zey Hotel

Zey Hotel
Greenport
CA $276
CA $315 total
includes taxes & fees
Sep 7 - Sep 8
Zey Hotel
Private beach, sun loungers, beach umbrellas, beach towels
Waterfront Beach Shack Studio
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Mini-fridge

7. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
  • Bask on a private sandy shore with seaside dining, umbrellas, and loungers at this waterfront escape in a nature reserve.
CA $489
CA $558 total
includes taxes & fees
Sep 23 - Sep 24
Silver Sands Motel & Beach Bungalows
Suite, 1 Bedroom, Terrace, Harbour View | Terrace/patio
Studio (Suite, King)
View from room
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers

8. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Beachside bliss awaits with sun loungers, umbrellas, and complimentary beach towels just a short 4-minute drive from this harborfront haven.
CA $328
CA $414 total
includes taxes & fees
Oct 1 - Oct 2
The Harbor Front Inn
Private beach
Condo
Flat-screen TV
Condo | Terrace/patio

9. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind on pristine shores with direct beach access, stunning sunsets, and spacious accommodations at this tranquil seaside aparthotel.
CA $420
CA $604 total
includes taxes & fees
Sep 21 - Sep 22
Cliffside Resort Condominiums
Lobby
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Lobby
Restaurant

10. Oyster Estate

Oyster Estate
Greenport
CA $412
CA $519 total
includes taxes & fees
Sep 7 - Sep 8
Oyster Estate
View all properties

Choose what matters most at beach hotels in Shelter Island Heights

Pool
Breakfast included
4 stars
5 stars
All-inclusive

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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Pleasant one night stay in our trek"
Carolyn 2-night trip
Posted less than an hour ago
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

10/10 Excellent
"Always a nice place and staff. Property dated a bit but always clean."
Gerard M 1-night trip
Posted less than an hour ago
Budget Host East End
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Everything"
Theresa 2-night trip
Posted 15 hours ago
Saybrook Point Resort & Marina
Kenny's Tipperary Inn

Kenny's Tipperary Inn

8/10 Good
"Room was clean and comfortable. Our room was on the second floor, steps were a chore"
Dennis 1-night trip
Posted 16 hours ago
Kenny's Tipperary Inn
Montauk Yacht Club

Montauk Yacht Club

8/10 Good
"Resort is beautiful, small lake, beautiful harbor, restaurants and hotel stunning. Room had a couple dirty, worn areas…lampshades, shower but overall nice."
mahsa 1-night trip
Posted 18 hours ago
Montauk Yacht Club
Marram

Marram

10/10 Excellent
"none"
ITALO 1-night trip
Posted 3 days ago
Marram

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 $315 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?
There are plenty of ways to save on a beach hotel in Shelter Island Heights. Join One Key™, our free travel rewards program, to unlock instant discounts with Member Prices across a range of hotels. Typically, booking in advance will help you save on your hotel. If you're feeling spontaneous, be sure to check for 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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