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Boston Bay Vacations

Pack those stellar shades. We have Boston Bay vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Boston Bay – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Boston Bay vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Boston Bay

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Boston Bay vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Boston Bay well.

Boston Bay Flight + Hotel packages

Top Hotel Deals

See all 38 Hotels in Boston Bay
Duncan's Hideaway Guesthouse

Duncan's Hideaway Guesthouse

Main Road, Boston Bay
3.0 out of 5.0

Situated near the beach, this guesthouse is 2.7 mi (4.4 km) from Boston Bay Beach and within 12 mi (20 km) of Rio Grande and Winnifred Beach. Folly Ruins and ...

Goblin Hill Villas at San San

Goblin Hill Villas at San San

San San, Port Antonio
3.5 out of 5.0

This family-friendly Port Antonio resort is located by the ocean, within 3 mi (5 km) of Winnifred Beach and Boston Bay Beach. Rio Grande and Musgrave Market ...

Frenchman's Cove Resort

Frenchman's Cove Resort

PO Box 101, Port Antonio
3.5 out of 5.0

Located in Drapers, this hotel is 2.7 mi (4.3 km) from Winnifred Beach and within 6 mi (10 km) of Rio Grande and Boston Bay Beach. Folly Ruins and Anglican Church ...

Hôtel Jamaïcan Colors

Hôtel Jamaïcan Colors

Ross Craig, Long Bay
3.5 out of 5.0

Situated in Long Bay, this beach hotel is within 12 mi (20 km) of Reach Falls, Boston Bay Beach, and Winnifred Beach. Rio Grande and Folly Ruins are also within ...

Great Huts

Great Huts

8-10 Boston Bay, Port Antonio
3.5 out of 5.0

This Port Antonio resort is on the beach, 0.2 mi (0.3 km) from Boston Bay Beach, and within 25 mi (40 km) of Reach Falls and Somerset Falls.

Hotel Tim Bamboo

Hotel Tim Bamboo

5 Eveleigh Park Road, Port Antonio
3.5 out of 5.0

Located in the heart of Port Antonio, this inn is within 1 mi (2 km) of Anglican Church and Rio Grande. Portland Parish Church and Folly Ruins are also within ...

$76

$76
Moon San Villa at the Blue Lagoon

Moon San Villa at the Blue Lagoon

Blue Hole Road, Drapers, Port Antonio
3.5 out of 5.0

Situated by the ocean, this hotel is in the same area as Winnifred Beach, Boston Bay Beach, and Folly Ruins. Area attractions also include Rio Grande and Anglican ...

Jamaica Palace Hotel

Jamaica Palace Hotel

Williamsfield, Port Antonio
4.0 out of 5.0

Situated by the ocean, this hotel is 2.5 mi (4 km) from Folly Ruins and within 6 mi (10 km) of Rio Grande and Port Antonio Square. Musgrave Market and Fort George ...

$125

$125
Tropical Lagoon Resort

Tropical Lagoon Resort

Blue Hole Road, Port Antonio
3.5 out of 5.0

Nestled on the beach, this Port Antonio hotel is 1.2 mi (2 km) from Winnifred Beach and 2.4 mi (3.9 km) from Boston Bay Beach. Rio Grande and Errol Flynn Marina ...

$135

$135
Villa Juanita

Villa Juanita

Hector's River, Happy Grove
4.0 out of 5.0

Situated near the beach, this hotel is 5 mi (8.1 km) from Reach Falls and 15 mi (24.2 km) from Boston Bay Beach.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.