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Hotels in The Heights, Shelter Island Heights from CA $170

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The Heights hotels and places to stay

Sound View Greenport
Seasonal outdoor pool, pool umbrellas, sun loungers

Sound View Greenport

4.0 star property
8.4 out of 10, Very good, (493)
"Amazing view. Would stay here again. Breakfast limited but great croissants. "
The price is CA $252
CA $322 total
includes taxes & fees
Dec 30 - Dec 31
Sound View Greenport
Baron's Cove
Front of property - evening/night

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (200)
"The place was great and maintained very well. Staff always helpful. "
The price is CA $358
CA $449 total
includes taxes & fees
Dec 30 - Dec 31
Baron's Cove
The Harbor Front Inn
Harbor View King | View from room

The Harbor Front Inn

3.5 star property
8.8 out of 10, Excellent, (422)
"the lady at the desk is amazing "
The price is CA $218
CA $279 total
includes taxes & fees
Jan 6 - Jan 7, 2025
The Harbor Front Inn
The Atlantic Hotel
Outdoor pool

The Atlantic Hotel

2.5 star property
7.0 out of 10, Good, (826)
"Very clean, quiet location. Close to food locations. Lots of space"
The price is CA $170
CA $230 total
includes taxes & fees
Jan 3 - Jan 4, 2025
The Atlantic Hotel
The Bentley Hotel Southampton
Terrace/patio

The Bentley Hotel Southampton

2.0 star property
9.4 out of 10, Exceptional, (213)
"Just 10 minute drive to restaurants. Newly renovated hotel. Very friendly staff."
The price is CA $231
CA $263 total
includes taxes & fees
Jan 5 - Jan 6, 2025
The Bentley Hotel Southampton
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (121)
"close to amenities. "
The price is CA $291
CA $379 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Journey East Hampton
The Hampton Maid
Property grounds

The Hampton Maid

2.5 star property
9.0 out of 10, Wonderful, (582)
"A rustic setting but everything was modern and clean. It’s easy to get to and near the bay."
The price is CA $355
CA $406 total
includes taxes & fees
Dec 29 - Dec 30
The Hampton Maid
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (120)
"Amazing place. "
The price is CA $704
CA $809 total
includes taxes & fees
Dec 29 - Dec 30
Topping Rose House
The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (126)
"I really liked the manager Shelby. She went above and beyond to make us feel welcome. She was hospitable, warm and friendly. The room was new, however the bathroom was very small and it was challenging to adjust the water temperature in the shower .But overall it exceeded my expectations. "
The price is CA $229
CA $311 total
includes taxes & fees
Jan 5 - Jan 6, 2025
The Sagaponack
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
8.8 out of 10, Excellent, (59)
"Lovely building. Our room was great. Staff were very nice and accommodating. We would definitely return."
The price is CA $359
CA $410 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Mill House Inn
The Menhaden
Property entrance

The Menhaden

3.5 star property
9.6 out of 10, Exceptional, (135)
"Beautiful hotel! We really loved all the staff and cleanliness of it. The Galley was the best part!!! We will definitely come back. "
The price is CA $243
CA $335 total
includes taxes & fees
Jan 12 - Jan 13, 2025
The Menhaden
Sag Harbor Inn
Outdoor pool

Sag Harbor Inn

3.5 star property
9.4 out of 10, Exceptional, (495)
"The scenery is beautiful. Hotel is in great location. Hotel is Very nice and clean! Very important. Not modern but very nice. New bathrooms. People are very nice and helpful. Continental breakfast included On our way to try it now. "
The price is CA $300
CA $342 total
includes taxes & fees
Dec 24 - Dec 25
Sag Harbor Inn
Canoe Place Inn and Cottages
Garden

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (36)
"Everything is delightful, love all the thoughtful attention to detail and luxuries so much I’ve decided to extend my stay. "
The price is CA $562
CA $674 total
includes taxes & fees
Dec 26 - Dec 27
Canoe Place Inn and Cottages
East Hampton House Resort
Deluxe Studio | Living area

East Hampton House Resort

3.0 star property
9.0 out of 10, Wonderful, (241)
"There is value in this if you think it is the most expensive neighborhood in L.I. Large garden, pool. Vicinity to Carissa and Goldberg for breakfast."
The price is CA $266
CA $335 total
includes taxes & fees
Jan 6 - Jan 7, 2025
East Hampton House Resort
Hamlet Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

2.0 star property
8.4 out of 10, Very good, (379)
"Wonderful stay "
Hamlet Inn
Southampton Inn
Traditional Single Room, 1 King Bed

Southampton Inn

3.0 star property
8.6 out of 10, Excellent, (510)
"Beautiful boutique hotel in awesome Southampton. Outdoor heated pool. Beautiful gardens. Easy walk to restaurants and shops. Nice venue for small wedding or event."
The price is CA $287
CA $351 total
includes taxes & fees
Dec 27 - Dec 28
Southampton Inn
Southampton Long Island Hotel
Desk, free WiFi, bed sheets

Southampton Long Island Hotel

2.5 star property
8.4 out of 10, Very good, (186)
"Nice hotel conveniently located "
The price is CA $171
CA $203 total
includes taxes & fees
Jan 20 - Jan 21, 2025
Southampton Long Island Hotel
The Roundtree, Amagansett
Beach nearby, white sand, sun loungers, beach umbrellas

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (85)
"My wife and I stayed a couple nights in October. We felt very pampered. Felix served us up late night snacks with homemade cookies and ice cream! Beautiful and charming hotel with attentive staff."
The price is CA $854
CA $1,024 total
includes taxes & fees
Dec 26 - Dec 27
The Roundtree, Amagansett
American Beech Hotel
Gift shop

American Beech Hotel

3.5 star property
9.0 out of 10, Wonderful, (170)
"Good customer service at check-in. Received a text at 1pm to note that room was clean and we could check in early. Also received a discount voucher to use at their restaurant for my husband’s birthday. Nice touch! The room was beautiful and clean, with all the amenities. Enjoyed the breakfast picnic basket included with the room the next morning. We loved everything except the room was cold and we couldn’t seem to operate the remote to increase the temperature. Also, our room was above a...
The price is CA $193
CA $277 total
includes taxes & fees
Jan 20 - Jan 21, 2025
American Beech Hotel
Hotel Moraine
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas

Hotel Moraine

2.0 star property
9.6 out of 10, Exceptional, (18)
"Quiet beautiful property "
The price is CA $284
CA $373 total
includes taxes & fees
Jan 9 - Jan 10, 2025
Hotel Moraine
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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Frequently asked questions

What is The Heights like?

Guests are sure to enjoy their time checking out all that Shelter Island Heights's The Heights neighborhood has to offer. Be sure to check out Sunset Beach and Shelter Island Country Club as part of your The Heights travel plans.

Where is the best place to stay in The Heights?

Based on Expedia customer reviews, The Chequit is the highest ranked property in The Heights. This hotel offers a restaurant and free parking.

How many hotels will I find in the The Heights area?

If you're searching for places to stay in Shelter Island Heights, choose from one of Expedia's 15 hotels and other accommodations in The Heights.

If I need to cancel my hotel reservation in The Heights, will I receive a refund?

Yes, most hotel bookings are fully refundable if cancelled prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best options available in The Heights.

Where can I learn more about changing or cancelling my trip to The Heights?

To find more details about picking new dates or cancelling your trip to The Heights, click here.

What are the top things to see and do in The Heights?

A few attractions you might want to check out while you're in The Heights are Sunset Beach and Shelter Island Country Club. While you're out sightseeing, Sylvester Manor and Crescent Beach are a couple of additional sights to visit in Shelter Island Heights.