Shelter Island Heights Holiday Rentals, New York: Private House Rentals

Our top choices for Shelter Island Heights hotels

The Pridwin Hotel

Shelter Island Heights

Rita

฿23,016 total

includes taxes & fees

24 Jun - 25 Jun

Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

Shelter Island Heights

Leslie

฿8,234 total

includes taxes & fees

24 Jun - 25 Jun

House on Chase Creek

The Heights

Robert

฿10,387 total

includes taxes & fees

16 Jun - 17 Jun

Shelter Island House

Shelter Island Heights

Dorothy

฿7,583 total

includes taxes & fees

15 Jun - 16 Jun

The Chequit

The Heights

Peter

฿21,464 total

includes taxes & fees

22 Jun - 23 Jun

Clinton Motel

Clinton

Bryan

฿3,711 total

includes taxes & fees

23 Jun - 24 Jun

Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Quality Inn Old Saybrook - Westbrook

Old Saybrook

Pamela

฿4,288 total

includes taxes & fees

21 Jun - 22 Jun

The Captain Stannard

Westbrook Center

GAIL

฿8,549 total

includes taxes & fees

17 Jun - 18 Jun

Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Freddy

฿3,878 total

includes taxes & fees

18 Jun - 19 Jun

Best Western Niantic - New London/Mystic Area

Niantic

Melanie

฿4,096 total

includes taxes & fees

12 Jul - 13 Jul

Lamplighter Motel - Clinton, Connecticut

Clinton

Edward

฿2,991 total

includes taxes & fees

23 Jun - 24 Jun

Inn at Harbor Hill Marina

Niantic

Mary Jo

฿10,582 total

includes taxes & fees

15 Jun - 16 Jun

The Niantic Inn

Niantic

Joshua

฿7,191 total

includes taxes & fees

14 Jun - 15 Jun

Motel 6 Niantic, CT - New London

Niantic

Linda

฿3,407 total

includes taxes & fees

18 Jun - 19 Jun

The Hampton Maid

Hampton Bays

Dawn

฿14,753 total

includes taxes & fees

23 Jun - 24 Jun

Water's Edge Resort & Spa

Westbrook Center

Maria Felicitas

฿14,189 total

includes taxes & fees

18 Jun - 19 Jun

The Scranton Seahorse Inn

Madison Center

Brian

฿12,937 total

includes taxes & fees

24 Jun - 25 Jun

Zey Hotel

Greenport

Jill

฿6,783 total

includes taxes & fees

25 Jun - 26 Jun

Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

Robert

฿3,049 total

includes taxes & fees

22 Jun - 23 Jun

Westbrook Inn B&B

Westbrook Center

Ashley

฿11,797 total

includes taxes & fees

14 Jun - 15 Jun

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Where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas for the activities you enjoy most.

The Heights

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

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view of wetland from the Marine Park Salt Marsh Nature Trail in brooklyn, new york (with gil hodges bridge to the rockaways int he background) cloud reflections in bay, water (shell bank creek)

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.

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Stay near popular Shelter Island Heights attractions

Crescent Beach

4.7/5 (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.

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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

Top Shelter Island Heights Hotel Reviews

Ocean Resort Inn

10/10 Excellent

"You can’t beat the location of this hotel, steps from the beach, and steps from town. Our room was very beachy, had great AC, and very clean. This property has a nice pool as well. I would not hesitate to book this property again."

Zey Hotel

10/10 Excellent

"Pros: Rooms were very clean and decorated nicely. Helpful staff welcoming. One parking spot Per room in back off Street. Had a nice seating areas throughout the games quiet corners to read. Plenty of shopping and restaurants been walking distance. Con: say it's early in the season as I stayed in the beginning of June. But the outdoor patio and gardens needed some attention and trimming. I would assume once the season gets going that this will be a manicured better."

Beachcomber Resort at Montauk

6/10 Okay

"We stayed for Memorial Day weekend, I would assume a busy holiday for them, and the entire time they were doing construction on the room above ours. We heard banging, drilling, and stomping for hours on end. They should maybe have waited during the week or not a busy holiday to make these renovations. When we called the front desk they said other people have also complained and that they will get it figured out, but it did not stop. In fact, we heard them talking and the workers and staff were annoyed/frustrated about the complaints made by the guests. Definitely disrupted our stay as we were trying to have a relaxing vacation."

Hyatt Place Long Island East End

10/10 Excellent

"The property itself was nice, and the breakfast was good with a decent selection of options. However, the cleanliness of the room was disappointing. There was a noticeable layer of dust on the tables, coffee machine, and even the glasses, which gave the impression that the room had not been thoroughly cleaned before my stay. While the hotel has some positive aspects, housekeeping standards need improvement."

Gurney's Montauk Resort & Seawater Spa

6/10 Okay

"Great location, excellent facilities. Staff very mixed - some incredible and some terrible. Cumulative number of issues but dealt with by a member of the management team after getting fed up of a number of things, Including: Dog mess left for > 24 hours after reporting it. Staff member laughed and clearly did nothing after reporting it. Not our dog. Had to call 4 times to get our daughters bed made up in the room. Despite being on the booking months in advance. Asked for an ice cream for our daughter and told i was lying when i said they’d done it for her the two proceeding days and they couldnt get her one. Not the kind of treatment or experience from a resort of this quality."

The Bentley Hotel Southampton

10/10 Excellent

"The room was clean and nice. Having 4 kids with us it was upsetting that the ac in the living room didn’t work and the shower head was not functioning properly and had very low water pressure. There’s 2 tvs but only 1 remote was provided. Other than the few things we enjoyed our stay."

The Pridwin Hotel

10/10 Excellent

"We had an absolutely enchanting long weekend at the Pridwin. This beautifully appointed property exudes timeless elegance, with thoughtful touches that made us feel truly pampered from the moment the staff reached out to us long before our stay. The complimentary breakfast, in-room snacks and drinks, outdoor fire pits with rocking chairs, and cozy nights spent by the fireplace with bar service turned our visit into a heartfelt home away from home — far warmer and more inviting than any sterile hotel experience. The outdoor heated pool was simply divine, backed by attentive and friendly service that made every swim a pleasure. Shelter Island offers the perfect backdrop for adventure and relaxation — exploring nearby vineyards to the north, or heading south by ferry to Sag Harbor and the broader Hamptons — all while knowing you can retreat each evening to this quiet, serene haven. A special shoutout to Tony, the bartender, whose genuine warmth and friendliness made us feel so welcome every time we crossed paths. Not to mention, he crafts exquisite cocktails and martinis that truly elevated our evenings."

More cheap stays in Shelter Island Heights

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

฿3,372

฿3,878 total

18 Jun - 19 Jun

includes taxes & fees

8/10 Very Good! (1,001 reviews)

Frequently asked questions

Where is the best place to stay in Shelter Island Heights?

The Pridwin Hotel is one of the top choices for your stay based on our traveller data. This hotel offers a full-service spa and a private beach. Two other choices for your stay in the area are Gurney's Montauk Resort & Seawater Spa and Montauk Manor. See all available top hotels, or 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 Railroad Museum of Long Island and East End Seaport Maritime Museum 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 breakfast. 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 41 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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Our top choices for Shelter Island Heights hotels

The Pridwin Hotel

West Neck Guesthouse

House on Chase Creek

Shelter Island House

The Chequit

Clinton Motel

Quality Inn Old Saybrook - Westbrook

The Captain Stannard

Pier Blue Inn Old Saybrook - Essex

Best Western Niantic - New London/Mystic Area

Lamplighter Motel - Clinton, Connecticut

Inn at Harbor Hill Marina

The Niantic Inn

Motel 6 Niantic, CT - New London

The Hampton Maid

Water's Edge Resort & Spa

The Scranton Seahorse Inn

Zey Hotel

Econo Lodge Inn & Suites Old Saybrook Westbrook

Westbrook Inn B&B

Where to stay in Shelter Island Heights

The Heights

Hay Beach

Stay near popular Shelter Island Heights attractions

Crescent Beach

Learn more about Shelter Island Heights

Top Shelter Island Heights Hotel Reviews

Ocean Resort Inn

More cheap stays in Shelter Island Heights

Pier Blue Inn Old Saybrook - Essex

Frequently asked questions

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