A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights hotels from HK$736

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Check prices for these dates

Tonight
10 Sept - 11 Sept
Tomorrow
11 Sept - 12 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

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Our top choices for Shelter Island Heights hotels

Terrace/patio
Beach
Pool
Room

1. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
HK$3,975
HK$4,996 total
includes taxes & fees
13 Sept - 14 Sept
The Pridwin Hotel
Outdoor dining
Room
View from room
Room

2. The Chequit

The Chequit
The Heights
United States
Kathleen
HK$1,623
HK$1,855 total
includes taxes & fees
4 Oct - 5 Oct
The Chequit
View from property
Exterior
A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.
Property grounds

3. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
HK$1,688
HK$1,929 total
includes taxes & fees
5 Oct - 6 Oct
House on Chase Creek
Front of property – evening/night
Property amenity
Property amenity
Terrace/patio

4. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
HK$1,578
HK$1,803 total
includes taxes & fees
12 Oct - 13 Oct
Shelter Island House
Room
Property grounds
Living room
Parking

5. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
HK$2,458
HK$2,809 total
includes taxes & fees
16 Sept - 17 Sept
West Neck Guesthouse
Beach bar
Room
Room
Beach

6. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sirikhwan
HK$2,166
HK$2,475 total
includes taxes & fees
12 Oct - 13 Oct
Silver Sands Motel & Beach Bungalows
Property entrance
Lobby
Restaurant
Meeting facility

7. The Menhaden

The Menhaden
Greenport
United States
Lisa
HK$3,029
HK$3,775 total
includes taxes & fees
13 Sept - 14 Sept
The Menhaden
Terrace/patio
Pool
Room
Room

8. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Michael
HK$2,040
HK$2,554 total
includes taxes & fees
4 Oct - 5 Oct
The Harbor Front Inn
Exterior
Bar (on property)
Restaurant
Room

9. Zey Hotel

Zey Hotel
Greenport
United States
Renee
HK$1,323
HK$1,512 total
includes taxes & fees
15 Sept - 16 Sept
Zey Hotel
Resort view
Restaurant
Beach
Yoga

10. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
HK$2,083
HK$2,604 total
includes taxes & fees
1 Oct - 2 Oct
Sound View Greenport
Terrace/patio
Room
Room
Beach

11. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
HK$2,266
HK$3,288 total
includes taxes & fees
5 Oct - 6 Oct
Cliffside Resort Condominiums
Pool
Restaurant
Lobby
Exterior

12. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
HK$2,698
HK$3,399 total
includes taxes & fees
12 Oct - 13 Oct
Oyster Estate
Terrace/patio
View from property
Bar (on property)
Restaurant

13. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
HK$2,437
HK$3,098 total
includes taxes & fees
21 Sept - 22 Sept
American Beech Hotel
Living area
Living room
Balcony
Private kitchen

14. North Fork Resort

North Fork Resort
Greenport
United States
Lisa
HK$2,520
HK$2,879 total
includes taxes & fees
28 Sept - 29 Sept
North Fork Resort
Exterior
Restaurant
Private kitchen
Front of property

15. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
HK$1,583
HK$2,004 total
includes taxes & fees
1 Oct - 2 Oct
The Shoals Suites and Slips
Building design
Breakfast area
Lobby
Lobby lounge

16. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Loretta
HK$2,541
HK$2,903 total
includes taxes & fees
4 Oct - 5 Oct
Sag Harbor Inn
Pool
Lobby lounge
Reception
Restaurant

17. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Joseph
HK$3,741
HK$4,701 total
includes taxes & fees
5 Oct - 6 Oct
Faraway Sag Harbor
Lobby
Breakfast area
Lobby sitting area
Pool

18. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Theresa
HK$793
HK$912 total
includes taxes & fees
4 Oct - 5 Oct
Quality Inn Old Saybrook - Westbrook
Living area
Room
Business centre
Exterior

19. The Captain Stannard

The Captain Stannard
Westbrook Center
United States
Deborah
HK$1,834
HK$2,036 total
includes taxes & fees
17 Sept - 18 Sept
The Captain Stannard
Bar (on property)
Exterior
Restaurant
Exterior

20. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
United States
DONNA
HK$1,406
HK$1,752 total
includes taxes & fees
7 Oct - 8 Oct
Water's Edge Resort & Spa
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Where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas for the activities you enjoy most.
A calm lake reflecting trees and a clear sky.
Photo by Erisa Dilo

The Heights

If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

When in Hay Beach, you can plan a visit to Greenport Carousel and Greenport Harbor Brewing Company, some noteworthy sights in the nearby area.

Stay near popular Shelter Island Heights attractions

Crescent Beach

9.4/10 (13 reviews)
Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
See properties

Shelter Island Country Club

10.0/10 (3 reviews)
Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.
See properties

Menhadden Lane Beach

8.8/10 (3 reviews)
Why not spend a care-free afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?
See properties

Sylvester Manor

8.8/10 (3 reviews)
You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets.
See properties

Learn more about Shelter Island Heights

Victorian homes line the streets of this charming hamlet where you can rent bikes to explore the island's quiet beaches. Reserve a table at one of the waterfront restaurants for sunset views or take the short ferry to Greenport for more dining options.

See all hotels in Shelter Island Heights
A pebbled beach with a sunset and a distant bridge.

Top Shelter Island Heights Hotel Reviews

Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"The staff were professional and very helpful. The room was clean and the view from the balcony was beautiful. The resort itself needs painting and updates otherwise everything else was wonderful."
Carmen 1-night trip
Posted 10 hours ago
Ocean Surf Resort
Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"Front desk staff was extremely knowledgeable, friendly and accommodating. The beach crew was excellent too. They set up and brought back all the necessities so all you had to do was relax."
Geraldine 1-night trip
Posted 1 day ago
Montauk Blue Hotel
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Very good"
Iosif 1-night trip
Posted 2 days ago
Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

10/10 Excellent
"Excellent service, beautiful property, accommodating staff."
Maria 3-night trip
Posted 2 days ago
Montauk Manor
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Welcoming, helpful, friendly, professional front desk staff. My room was impeccably clean and tidy. The property is centrally-located with ease of accessibility to main roads and major highways, yet far enough off Boston Post Road to ensure a quiet, peaceful and restful stay. Overall, an outstanding, no-frills property! I look forward to staying here once again!"
Marc 1-night trip
Posted 3 days ago
Pier Blue Inn Old Saybrook - Essex

More cheap stays in Shelter Island Heights

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
HK$640
HK$736 total
16 Sept - 17 Sept
includes taxes & fees
8/10 Very good! (1,001 reviews)
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
HK$698
HK$797 total
13 Sept - 14 Sept
includes taxes & fees
Budget Host East End
Kenny's Tipperary Inn

Kenny's Tipperary Inn

432 West Lake Drive Montauk NY
HK$843
HK$1,002 total
8 Oct - 9 Oct
includes taxes & fees
Kenny's Tipperary Inn
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
HK$935
HK$1,264 total
1 Oct - 2 Oct
includes taxes & fees
The Atlantic Hotel
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
HK$1,090
HK$1,586 total
27 Sept - 28 Sept
includes taxes & fees
8.6/10 Excellent! (309 reviews)
Ocean Surf Resort
Montauk Blue Hotel

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY
HK$1,133
HK$1,678 total
27 Sept - 28 Sept
includes taxes & fees
9.2/10 Wonderful! (270 reviews)
Montauk Blue Hotel

Hotels in Shelter Island Heights with star-rating

Frequently asked questions

Where is the best place to stay in Shelter Island Heights?
The Chequit is one of the top choices for your stay based on our traveller data. This hotel offers a restaurant and free parking. Other good choices for your stay include The Pridwin Hotel and West Neck Guesthouse. See all available top hotels, or vacation rentals in Shelter Island Heights.
What are some of the best holiday rentals that Shelter Island Heights has to offer?
Unobstructed Ocean Views ! A Beautiful Montauk Getaway: This holiday home rental outside of Shelter Island Heights is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden. See all vacation rentals in Shelter Island Heights.
If I need to cancel my hotel reservation in Shelter Island Heights, will I receive a refund?
Yes, most hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, you might still have the option to cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island Heights.
What's the best family accommodation in Shelter Island Heights?
The Pridwin Hotel is a hotel with a private beach and a restaurant, and it's a top choice on Expedia for families. Shelter Island House is another good choice for your child-friendly holiday. Also, attractions in the area such as East End Seaport Maritime Museum and Railroad Museum of Long Island are fun for children of all ages. Find more child-friendly accommodations in Shelter Island Heights.
What's the best dog-friendly accommodation option in Shelter Island Heights?
The Chequit is a top hotel for people travelling with their pets, and offers a restaurant and a coffee shop/cafe for its human guests. SEVEN - Shelter Island Guest House is another good option if you're bringing your pet along. See more pet-friendly hotel accommodations in Shelter Island Heights.
What's the best place to stay to stay near the beach in Shelter Island Heights?
The Pridwin Hotel is a top beachfront hotel offering a seasonal outdoor pool and free breakfast, located within a short 1-minute walk of Crescent Beach . See more stays near the beach in Shelter Island Heights.
What's the best accommodation for a golf trip to Shelter Island Heights?
Shelter Island House is a top hotel that has an adjacent golf course and features free WiFi. Other good options to stay near a golf course include House on Chase Creek and SEVEN - Shelter Island Guest House. You can tee off at Shelter Island Country Club during your trip. See more golf hotels in Shelter Island Heights.
What are some accommodation options with pools in Shelter Island Heights?
The Pridwin Hotel is a top hotel with a seasonal outdoor pool, a private beach and a full-service spa. View all hotels with pools in Shelter Island Heights.
What is the best spa hotel in Shelter Island Heights?
The Pridwin Hotel is a top spa hotel featuring a private beach, a fitness centre, a bar and a restaurant. Spend an afternoon at Pridwin Spa where you'll find facials, body scrubs, and Swedish massages and more. See all spa hotels in Shelter Island Heights.
How is it to stay in Shelter Island Heights?
Visitors to Shelter Island Heights will definitely enjoy the beaches. Tourists can also enjoy the city's golf courses, entertainment choices and theatres. In Shelter Island Heights, there are 45 hotels and other accommodation options to choose from. Find out more about Shelter Island Heights.
What should I do while I'm visiting Shelter Island Heights?
Natural beauty is on display at Sunset Beach, Crescent Beach and Menhadden Lane Beach. A couple of additional sights to add to your itinerary are Shelter Island Country Club and Sylvester Manor. Take a look at what more there is to see and do in Expedia's Shelter Island Heights guide.
What's the weather like in Shelter Island Heights?
The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island Heights is 1452 mm.

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