The Heights Vacations from $222

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Your The Heights Vacation

Your next great escape is just around the corner with a vacation package to The Heights. Entertainment, relaxation and great times — you're bound to find it in this neighborhood. Not sure what to do and see during your trip to The Heights? Nearby attractions like Sunset Beach, Crescent Beach and Shelter Island Country Club are good places to start. Expedia will help put your plans into action. Book your perfect The Heights vacation now.

The Latest The Heights Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $463, price is now $222 per person
$222
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
15.6/10 Exceptional! (80 reviews)
I wish there was a coffee maker in the room, also the TV was very small and angled away from the bed. It was super quiet, which was great, and very clean and warm.

Reviewed on Nov 16, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $646, price is now $315 per person
$315
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
17.2/10 Exceptional! (2,613 reviews)
The location was ideal for our stay. The restaurant food was amazing.

Reviewed on Nov 22, 2025

Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

3 out of 5
Price was $458, price is now $229 per person
$229
per person
Jan 30 - Feb 3
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
16.8/10 Exceptional! (1,001 reviews)
Beautiful place to be

Reviewed on Nov 20, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $574, price is now $302 per person
$302
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18.4/10 Exceptional! (1,002 reviews)
I stay here often and the rooms are spacious clean and the hotel staff is very accommodating. I always have a wonderful experience and I highly recommend staying here. They also offer free breakfast and dinner which is a nice perk.

Reviewed on Nov 25, 2025

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Price was $422, price is now $222 per person
$222
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18/10 Exceptional! (1,825 reviews)
I had a great experience there and a very comfortable stay

Reviewed on Nov 25, 2025

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The Chequit

The Chequit

3 out of 5
23 Grand Ave Shelter Island Heights NY
8.8/10 Excellent! (37 reviews)
A cozy room with great pillows and quiet. Perfect little place.

Reviewed on Oct 10, 2025

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The Chequit
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Dec 2 to Dec 3
$116 total
Dec 2 - Dec 3
Total with taxes and fees
7.6/10 Good! (1,007 reviews)
Staff was kind. Easy, comfortable stay.

Reviewed on Nov 19, 2025

Quality Inn Old Saybrook - Westbrook
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$203 nightly
The price is $232 total per night from Nov 26 to Nov 27
$232 total
Nov 26 - Nov 27
Total with taxes and fees
8.4/10 Very Good! (593 reviews)
Amazing views and comfy bed and room. No sound privacy between the rooms at all! I guess they o relooked sound insulation in an otherwise gorgeous renovation of a roadside motel.

Reviewed on Nov 19, 2025

Sound View Greenport
See all 3,986 properties in The Heights
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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Discover the most popular places to visit in The Heights

Shelter Island Country Club

Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.

Shelter Island Country Club

Sunset Beach

4.5/5(9 reviews)

Why not spend a carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.

Sunset Beach

Crescent Beach

4.5/5(4 reviews)

Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.

Crescent Beach

Things to do

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

$179
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
See all activities in Shelter Island Heights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.