The Heights Hotels near Shelter Island Heights

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Sep 25 - Sep 26
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Sep 26 - Sep 27
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Sep 26 - Sep 28
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Oct 3 - Oct 5

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Top Trending Hotels Near The Heights, Shelter Island Heights

House on Chase Creek
View from property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (76)
"It was a peaceful and serene as it gets what a nice overnight stay we will have to come back again to explore more sometime soon. "
The price is P12,332
P14,090 total
includes taxes & fees
Oct 2 - Oct 3
House on Chase Creek
The Chequit
Exterior

The Chequit

3.0 star property
9.0 out of 10, Wonderful, (36)
"Everyone was amazing "
The Chequit
The 1770 House Restaurant & Inn
Garden

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (157)
"The staff was incredibly genuine and the property felt intimate and comfortable."
The price is P18,677
P25,533 total
includes taxes & fees
Oct 6 - Oct 7
The 1770 House Restaurant & Inn
Silver Sands Motel & Beach Bungalows
Beach bar

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (127)
"We had a great time, it’s a beautiful property and there’s plenty to do downtown. It was our first time here and we’ll definitely be back. "
Silver Sands Motel & Beach Bungalows
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
9.8 out of 10, Exceptional, (168)
"Beautiful place and wonderful staff"
The price is P12,755
P14,158 total
includes taxes & fees
Oct 2 - Oct 3
Westbrook Inn B&B
Canoe Place Inn and Cottages
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Canoe Place Inn and Cottages

4.0 star property
9.8 out of 10, Exceptional, (56)
"Amazing property. Really enjoyed our stay."
Canoe Place Inn and Cottages
The Roundtree, Amagansett
Beach nearby, white sand, sun loungers, beach umbrellas

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (88)
"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "
The price is P34,193
P41,019 total
includes taxes & fees
Oct 1 - Oct 2
The Roundtree, Amagansett
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (77)
"Shelter Island is definitely a gem"
The price is P15,982
P20,085 total
includes taxes & fees
Oct 19 - Oct 20
The Pridwin Hotel
The Shoals Suites and Slips
Premium bedding, down comforters, individually decorated

The Shoals Suites and Slips

3.5 star property
9.6 out of 10, Exceptional, (206)
"Loved our stay"
The price is P13,918
P17,338 total
includes taxes & fees
Sep 28 - Sep 29
The Shoals Suites and Slips
The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (247)
"Everything was fantastic, will stay again!"
The Captain Stannard
The Menhaden
Property entrance

The Menhaden

3.5 star property
9.6 out of 10, Exceptional, (162)
"Great little boutique hotel. Staff were very helpful and accommodating. Great restaurants and wineries in the area. Would highly recommend!"
The price is P21,780
P27,183 total
includes taxes & fees
Oct 13 - Oct 14
The Menhaden
The Hedges Inn
Egyptian cotton sheets, premium bedding, in-room safe

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Great staff "
The Hedges Inn
The Bentley Hotel Southampton
Terrace/patio

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (341)
"Return visitor. Great stay."
The price is P10,209
P11,664 total
includes taxes & fees
Oct 1 - Oct 2
The Bentley Hotel Southampton
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (64)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
The price is P29,791
P34,037 total
includes taxes & fees
Oct 26 - Oct 27
East Hampton Art House Bed & Breakfast
James Pharmacy Bed & Breakfast
Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (18)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
The price is P15,623
P17,342 total
includes taxes & fees
Oct 2 - Oct 3
James Pharmacy Bed & Breakfast
Madison Beach Hotel
Exterior

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (319)
"the staff was exceptional and our dinner was very good"
The price is P19,493
P22,416 total
includes taxes & fees
Oct 26 - Oct 27
Madison Beach Hotel
Bridgehampton Inn
Outdoor wedding area

Bridgehampton Inn

3.5 star property
9.4 out of 10, Exceptional, (216)
"Lovely inn, with very accommodating staff. "
The price is P17,183
P19,632 total
includes taxes & fees
Oct 6 - Oct 7
Bridgehampton Inn
Sag Harbor Inn
Outdoor pool

Sag Harbor Inn

3.5 star property
9.4 out of 10, Exceptional, (555)
"Great place to stay!"
The price is P16,240
P18,555 total
includes taxes & fees
Oct 6 - Oct 7
Sag Harbor Inn
Saybrook Point Resort & Marina
Exterior

Saybrook Point Resort & Marina

3.5 star property
9.4 out of 10, Exceptional, (1010)
"Great place!! "
The price is P20,165
P24,626 total
includes taxes & fees
Oct 14 - Oct 15
Saybrook Point Resort & Marina
Greenporter Hotel
Property grounds

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (244)
"Staff was amazing and this hotel is in the perfect location "
The price is P11,400
P13,024 total
includes taxes & fees
Oct 5 - Oct 6
Greenporter 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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Where to stay in The Heights

Find the best The Heights areas and neighborhoods for the activities you enjoy most.

Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

Top The Heights Hotel Reviews

Sea Crest Resort

Sea Crest Resort

10/10 Excellent
"Good property, centrally located near both Montauk and East Hampton."
Linda 3-night trip
Posted 2 days ago
Sea Crest Resort

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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. Another top choice in the area is House on Chase Creek.

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 14 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.