North Side Vacations from $1,033

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Your North Side Vacation

Say farewell to the worries of planning and hello to a North Side vacation package. With everything organized before you take off, you can focus on discovering this city, starting with Renaissance, which is good for watersports, families and underwater activities. Starfish Beach, Grand Cayman Beaches and Rum Point Beach are just a few of the sights you'll want to see during your trip to North Side. Don't put off your visit to this city any longer. Your ultimate North Side vacation is a few clicks away with Expedia.

The Latest North Side vacation packages

Price found within the past 48 hours. Click for updated prices.
The Reef Beach Resort, East End, Grand Cayman

The Reef Beach Resort, East End, Grand Cayman

$1,033
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
8.4/10 Very Good! (1,084 reviews)
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

Save 100% on your flight
$1,129
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (787 reviews)
Great resort, very courteous staff, there was a $75/night resort fees not included in Expedia booking that I wasn’t aware of (probably my fault, I should have read the details better).

Reviewed on Aug 6, 2026

Point West Premier Rentals

Point West Premier Rentals

Northwest Point
$1,284
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (23 reviews)
Very spacious and clean. Would definitely stay there again. 🙃

Reviewed on Aug 3, 2026

Black Urchin

Black Urchin

Save 100% on your flight
$6,542
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
10/10 Exceptional! (3 reviews)
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight
$1,838
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (1,001 reviews)
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Stay near popular North Side attractions

Starfish Beach

8.6/10 (340 reviews)
If a restful vacation is part of your travel plans, Starfish Beach might be the perfect place to seek out during your trip to Rum Point. Wander the area's seaside or simply enjoy one of its seafood restaurants.
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Cayman Kai Public Beach

9.2/10 (7 reviews)
Why not spend a lazy afternoon at Cayman Kai Public Beach during your trip to Rum Point? Amble around the area's beautiful beaches or seek out the snorkeling spots.
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Queen Elizabeth II Botanic Park

8.6/10 (15 reviews)
Enjoy the beautiful coral reefs and explore Queen Elizabeth II Botanic Park, a lovely green space in Breakers. Stroll along the seaside in this relaxing area, or check out its top-notch restaurants.
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Cayman Crystal Caves

Commune with nature and explore the great outdoors at Cayman Crystal Caves during your travels in Old Man Bay.
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Mastic Trail North Trailhead

6.0/10 (3 reviews)
Explore the lovely green spaces of Mastic Trail North Trailhead and enjoy the snorkeling spots in North Side. Wander the beautiful beaches and seaside in this relaxing area.
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Mastic Trail South Trailhead

Explore the lovely green spaces of Mastic Trail South Trailhead and enjoy the snorkeling spots in Breakers. Wander the beautiful beaches and seaside in this relaxing area.
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What to do in North Side

Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point

Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point

$55
per adult
98% of travellers recommend
Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point
Stingray Sandbar, Snorkeling, and Starfish Point

Stingray Sandbar, Snorkeling, and Starfish Point

$60
per adult
100% of travellers recommend
Stingray Sandbar, Snorkeling, and Starfish Point
Horseback Beach Riding in the Grand Cayman

Horseback Beach Riding in the Grand Cayman

$100
per adult
94% of travellers recommend
Horseback Beach Riding in the Grand Cayman
See all activities in North Side

North Side Hotel Deals

On The Bay

On The Bay

67 Old Robin Rd North Side North Side
$502 nightly
$538 total
Aug 11 - Aug 12
Total with taxes and fees
On The Bay
The Place

The Place

110 Old Robin Rd Old Man Bay North Side
10/10 Exceptional! (13 reviews)
"Beautiful place with a clean, comfortable stay and everything we needed and even more. The check-in and check-out instructions were very clear and easy to follow. Parking was available, and the private entrance made everything feel convenient and secure. The location is excellent, close to spots ..."

Reviewed on May 27, 2026

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The Place
Cayman Luxury Rentals at Ocean Paradise

Cayman Luxury Rentals at Ocean Paradise

1234 Rum Point Road North Side Grand Cayman
9.8/10 Exceptional! (43 reviews)
"Family friendly, very equipped accommodation. Caring and quick responsive staff. Would definitely recommend the place."

Reviewed on Jul 11, 2026

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Cayman Luxury Rentals at Ocean Paradise
See all 1,468 properties in North Side
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.

Find the Best North Side Vacation Packages

North Side Beach Vacation

Listen to the waves breaking onto the shore and stroll by the shimmering waters on your North Side vacation. If you need a break from daily life, a trip to North Side is your ticket to fun and relaxation. We have a great range of North Side packages to select from. Snap up one near Starfish Beach, just 4 miles (7 km) from the center of town, and live out your vacation dreams without hurting your budget.

Things You Should Know About North Side

  • If fresh ocean breezes and water views are your idea of a dreamy escape, why not think about one of our North Side beach hotels? Staying near the water is the perfect antidote to life's daily stresses.
  • Private vacation homes are another top choice for travelers planning a vacation in North Side. Two great examples are Ocean Paradise and Parrot-ise Villa by Cayman Vacation.
  • Don't forget to visit our North Side things to do page for some trip planning inspiration. With a population of around 1,200 in North Side, we're sure there'll be one or two locals who'll be pleased to give you some extra advice!
  • North Side vacation deals are one of the best ways to save on exciting experiences. Some ideas, such as Starfish Beach, Mastic Trail North Trailhead and Mastic Trail South Trailhead, belong at the very top of your must-do list.

North Side Essential Information

Language
English
Closest Airport
Owen Roberts Intl. Airport (GCM)
Population
1,200
Max Temp Winter
80ºF
Max Temp Summer
85ºF
Top Sights
Seven Mile Beach, Governors Beach and Camana Bay

More vacations you might like

Frequently asked questions

How much does a North Side vacation package cost?
You'll find cheap prices from $1,033 on Expedia for your North Side break. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to North Side costs.
What are the cheapest months to go to North Side?
If you'd like to snag a cheap North Side vacation package, consider traveling in January, September and December. You'll usually find better rates on flights and hotels during these months — perfect for budget-conscious travelers.
How many days is enough for North Side?
With around 6 days, you'll have enough time to enjoy popular neighborhoods like Brinkleys and Breakers during your North Side vacation. Be sure to also add Star Fish Point and Cayman Kai Public Beach to your must-do list. Looking for more adventures? Consider exploring outside of North Side on day trips and tours.
Is it worth booking a vacation package to North Side?
Popular for its nature, dining and watersports, a North Side vacation has something for everyone. Be sure to visit key sights like Mastic Trail North Trailhead and Babylon, and consider renting a set of wheels for day trips to experience even more.
How to find the best North Side package deals?
Bagging a cheap North Side package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly North Side package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a North Side vacation as a package?
You can enjoy significant savings on your next North Side retreat by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to North Side?
If you're planning an impromptu North Side getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to North Side?
  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the activities on offer will also help you decide when to vacation in North Side.
  2. Set your budget: Factor in costs like food, flights and transportation when working out how much to set aside for your trip to North Side. Then, select a property that fits your budget, whether that's an economical option or a high-end retreat.
  3. Use Expedia's trip planning tool to explore North Side: Research every aspect of your trip to North Side with this handy planner. Invite your family and friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide your trip length: Think about how long you want to spend discovering North Side. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  5. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a North Side vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Read our dedicated travel guide to find some exciting things to do in North Side. Book tickets or make reservations before you go to save time and skip the hassle of looking for activities once you arrive.
Does Expedia offer Book Now, Pay Later North Side vacation packages?
Your North Side getaway should be a relaxing escape from your daily routine, not a source of money worries. So to allow you a bit more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.