The Heights Holidays

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Your The Heights Holiday

Book a The Heights holiday package and immerse yourself in the way of life and vibe of this vibrant neighbourhood. With all your travel plans worked out, the only thing you need to worry about here is having the time of your life. Begin your trip to The Heights with a visit to nearby attractions such as Sunset Beach, Crescent Beach and Sylvester Manor. Stop daydreaming and start doing. When it's time to book your holiday to The Heights, Expedia is here to help.

Top hotels in The Heights

Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is £71 per night from 24 Jun to 25 Jun
£71
per night
24 Jun - 25 Jun
7.6/10 Good! (797 reviews)
"Overall, this was a very good experience. The room was clean, including the bed and the bathroom. Everything worked as expected, and there was plenty of hot water for showering. The TV and the WiFi worked well. It felt safe. The property is convenient to all mid-shoreline activities. It was very ..."

Reviewed on 17 Jun 2024

Pier Blue Inn Old Saybrook - Essex
The Bentley Hotel Southampton
The Bentley Hotel Southampton
2 out of 5
161 Hills Station Rd, Southampton, NY
The price is £607 per night from 22 Jun to 23 Jun
£607
per night
22 Jun - 23 Jun
9.2/10 Wonderful! (89 reviews)
"After our hotel cancelled on us last minute, we rerouted to the Bentley Hotel. I’m glad we did. Staff were friendly, room was huge and grounds were well maintained. My family had a great Father’s Day weekend at this hotel."

Reviewed on 18 Jun 2024

The Bentley Hotel Southampton
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is £336 per night from 9 Jul to 10 Jul
£336
per night
9 Jul - 10 Jul
9.4/10 Exceptional! (1,002 reviews)
Delightful stay
"Delightful in every way. Particularly impressed by the service—reception, work crew (who rescued my locket from the drain!), and wait staff—all very helpful, efficient, and kind. We enjoyed the heated indoor pool, lovely view, and tasteful decor in our room. Would love to stay again"

Reviewed on 19 Jun 2024

Saybrook Point Resort & Marina
See all 4,093 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a The Heights travel package cost?
Perhaps less than you imagined — from a low , actually! By combining hotels, flights and car rentals into your own customized travel package, your trip to The Heights is just clicks away.
If I'm not able to travel, can I cancel my The Heights travel package?
We understand — sometimes life doesn’t go according to plan. If you’ve booked a The Heights travel package and need to amend or cancel it, we can help. We suggest looking up our Customer Service Portal first for information. But in general, if you’ve booked your package within 24 hours, you may be able to cancel or change your itinerary for free. If it’s been more than 24 hours, your airline, hotel or car rental company may impose a charge.
How do I get a cheap travel package to The Heights?
Crafting your own The Heights travel package with Expedia is an easy way to save. We offer more than 550 airlines and 1,000,000 hotel options globally. With such a broad range to pick from, you’ll have no worries putting together your next dream escape.
Does Expedia offer Book Now, Pay Later The Heights holidays?
Yes, we do. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply select the payment plan best suited to your needs during checkout and take away the stress of budgeting for your trip. Don’t forget to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Klarna has easy monthly payment plans that work for all budgets, so you can book that well-earned holiday sooner.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that “book now” button, go for a low deposit holiday payment plan with Klarna.

Where should I stay in The Heights?
With fascinating attractions such as Sylvester Manor and Crescent Beach in this area, try to find a hotel near either of them. Sunset Beach is another sight that travellers flock to.
What are the top hotels in The Heights?
House On Chase Creek and Shelter Island House are among the most well-known hotels in The Heights. Why not check out the rates and amenities at each and then make a decision?
How far in advance should I book my The Heights holiday?
Smart travellers often reserve their seats as early as possible. You can generally look up international fares on Expedia up to 12 months before your flight. If you’re booking last minute, fear not. Bargain prices occasionally appear just weeks before departure.
What does an Expedia The Heights travel package include?
Flights, hotels and rental cars, or any combination of the three — it’s up to you! Whether you’re venturing to The Heights with the whole family or travelling with your friends, there’s a package to match your style and budget. Once you’ve made your booking, why not add on some tours and experiences?
What should I know before booking a The Heights travel package?
When you book your flights, hotels and car rentals together, you’ll enjoy amazing discounts. Whether you’re organising an outdoor getaway in a chalet or want to stay in a convenient hotel in the city, Expedia can help make it happen.
Can I choose my airline with a The Heights Expedia travel package?
Yes, so take your pick! Expedia has access to more than 550 airlines throughout the world, so you can design your The Heights trip according to your needs and budget.

Popular places to visit

Image for Shelter Island Country Club

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
Image for Sunset Beach

Sunset Beach

Why not spend a care-free afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.

Sunset Beach
Image for Crescent Beach

Crescent Beach

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.

Crescent Beach

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.