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The Heights Hotels near Shelter Island Heights

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

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Our top choices for The Heights hotels

View from property
House on Chase Creek

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
The price is P6,116
P6,988 total
includes taxes & fees
Jan 12 - Jan 13, 2026
House on Chase Creek
Exterior
American Beech Hotel

American Beech Hotel

American Beech Hotel
3.5 star property
2.6 km from The Heights
8.8 out of 10, Excellent, (195)
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
The price is P14,800
P19,259 total
includes taxes & fees
Dec 29 - Dec 30
American Beech Hotel
Garden
The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
19.4 km from The Heights
9.8 out of 10, Exceptional, (161)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is P15,270
P20,876 total
includes taxes & fees
Dec 28 - Dec 29
The 1770 House Restaurant & Inn
Garden
The Huntting Inn

The Huntting Inn

The Huntting Inn
3.5 star property
19.4 km from The Heights
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
The price is P22,465
P26,253 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Huntting Inn
Exterior
Journey East Hampton

Journey East Hampton

Journey East Hampton
4.0 star property
20.7 km from The Heights
9.0 out of 10, Wonderful, (160)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
Journey East Hampton
Premium bedding, down comforters, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
4 km from The Heights
9.4 out of 10, Exceptional, (231)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is P10,894
P12,447 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Shoals Suites and Slips
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
23.1 km from The Heights
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is P5,241
P6,775 total
includes taxes & fees
Dec 28 - Dec 29
Hamlet Inn
Beach nearby, white sand, sun loungers, beach umbrellas
The Roundtree, Amagansett

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
21.4 km from The Heights
10.0 out of 10, Exceptional, (91)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
The price is P34,909
P41,877 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Roundtree, Amagansett
Seasonal outdoor pool
Head of Pond House

Head of Pond House

Head of Pond House
3.0 star property
18.3 km from The Heights
10.0 out of 10, Exceptional, (3)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
The price is P29,119
P33,269 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Head of Pond House
Breakfast and dinner served
Copper Beech Inn

Copper Beech Inn

Copper Beech Inn
4.0 star property
30.3 km from The Heights
8.6 out of 10, Excellent, (506)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is P16,386
P18,844 total
includes taxes & fees
Dec 28 - Dec 29
Copper Beech Inn
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
17.1 km from The Heights
8.8 out of 10, Excellent, (215)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is P9,462
P13,159 total
includes taxes & fees
Dec 29 - Dec 30
The Sagaponack
Property grounds
The Hampton Maid

The Hampton Maid

The Hampton Maid
2.5 star property
24.7 km from The Heights
9.0 out of 10, Wonderful, (688)
"Great place to stay"
United States
Mitchell
The price is P16,651
P19,023 total
includes taxes & fees
Dec 27 - Dec 28
The Hampton Maid
Outdoor pool
Topping Rose House

Topping Rose House

Topping Rose House
4.5 star property
16.5 km from The Heights
9.2 out of 10, Wonderful, (136)
"Great rooms, staff and food"
United Kingdom
Alexandra
The price is P31,451
P36,138 total
includes taxes & fees
Dec 27 - Dec 28
Topping Rose House
Garden
The Maidstone

The Maidstone

The Maidstone
4.0 star property
19.5 km from The Heights
8.0 out of 10, Very Good, (150)
"We had a wonderful stay "
United States
Sabrina
The price is P14,727
P16,826 total
includes taxes & fees
Dec 28 - Dec 29
The Maidstone
Aerial view
Southampton Inn

Southampton Inn

Southampton Inn
3.0 star property
22 km from The Heights
8.6 out of 10, Excellent, (550)
"Such a great location!"
United States
Elizabeth
The price is P11,746
P14,377 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Southampton Inn
Front of property - evening/night
Mill House Inn

Mill House Inn

Mill House Inn
5.0 star property
19.3 km from The Heights
9.0 out of 10, Wonderful, (75)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is P22,025
P38,752 total
includes taxes & fees
Dec 29 - Dec 30
Mill House Inn
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
2.3 km from The Heights
9.8 out of 10, Exceptional, (142)
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
Desk, free WiFi, bed sheets
Southampton Long Island Hotel

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
20.9 km from The Heights
8.6 out of 10, Excellent, (203)
"Good location. Nice people!! "
United States
Theresa
The price is P6,765
P8,068 total
includes taxes & fees
Dec 28 - Dec 29
Southampton Long Island Hotel
Terrace/patio
Westbrook Inn B&B

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
24 km from The Heights
9.8 out of 10, Exceptional, (177)
"Our stay was amazing! All the staff were so accommodating and kind. The inn has a rustic charm and was so festive for the holidays! Rooms are a good size, clean, and have everything you need. The breakfast was delicious and they even had free tea/coffee/cookies for all guests to enjoy :) "
United States
Chewon
The price is P13,299
P14,762 total
includes taxes & fees
Dec 29 - Dec 30
Westbrook Inn B&B
Exterior
Zey Hotel

Zey Hotel

Zey Hotel
3.5 star property
2.7 km from The Heights
9.2 out of 10, Wonderful, (290)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
Zey 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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Looks great "
Bahareh 1-night trip
Posted 3 days ago
Water's Edge Resort & Spa

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, House on Chase Creek is the highest ranked property in The Heights. This guesthouse offers free parking and free WiFi.
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 13 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.
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.

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