Two Boats Vacations from $427

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Your Two Boats Vacation

When you choose a Two Boats vacation package, you can relax and enjoy your getaway to the fullest. Discover the best parts of this unique city knowing that everything has been taken care of before you go. Eager to explore? Georgetown Beach, Boatswain Bird Island and Green Mountain are some of the leading places to visit during a trip to Two Boats. Expedia will help you escape your routine. Tailor your vacation to Two Boats to suit your style of travel, whatever that may be!

The Latest Two Boats vacation packages

Price found within the past 48 hours. Click for updated prices.
6080 Design Hotel by Eskape Collection

6080 Design Hotel by Eskape Collection

4 out of 5
Mid Beach
Save 100% on your flight
Price was $887, price is now $427 per person
$427
per person
Apr 22 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,002 reviews)
Very clean and taken care of

Reviewed on Jan 26, 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,611, price is now $695 per person
$695
per person
Apr 22 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Bed was comfortable. Vibe was funky and cool. Staff was friendly and helpful.

Reviewed on Feb 12, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $17,695, price is now $8,047 per person
$8,047
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,175, price is now $550 per person
$550
per person
Mar 22 - Mar 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
If you're looking for a super nice place to stay this is NOT that. It's an older hotel that serves It's purpose. Our room was very clean, AC was great, the bed & pillows are not comfortable but worked. The staff was extremely friendly. I would stay here again for a quick 2 night trip.

Reviewed on Feb 13, 2026

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Price was $1,833, price is now $858 per person
$858
per person
Apr 22 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (394 reviews)
A reasonably priced art deco hotel in a popular tourist area. Hotel and rooms are stylishly designed. Restaurant food was ok. Maria was a fabulous server. On the downside, there is no pool or fitness center.

Reviewed on Jan 12, 2026

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Two Boats Hotel Deals

Mantis St Helena

Mantis St Helena

4 out of 5
1-3 Main Street Jamestown
$279 nightly
The price is $279 total per night from Feb 19 to Feb 20
$279 total
Feb 19 - Feb 20
Total with taxes and fees
9.2/10 Wonderful! (10 reviews)
Great hotel, excellent location, comfortable well-equipped rooms but what made this place special was the staff. Everyone was helpful and sociable, nothing was too much trouble. I would happily stay here again.

Reviewed on Dec 1, 2025

Mantis St Helena
Richards Travel Lodge

Richards Travel Lodge

3.5 out of 5
49 Emirates Way Jamestown
9.4/10 Exceptional! (6 reviews)
Enjoying Saint helene
Very comfortable and the couple is really very nice and helpfull

Reviewed on Feb 27, 2024

Get rates
Richards Travel Lodge
Enchanting 1-bedroom lodge in Saint Helena

Enchanting 1-bedroom lodge in Saint Helena

Saint Helena Saint Helena
Get rates
Enchanting 1-bedroom lodge in Saint Helena
See all 3 properties in St. Helena
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 Two Boats Vacation Packages

Two Boats Essential Information

Language
English
Currency
St. Helena pounds
Top Sights
Georgetown Beach, Green Mountain and Boatswain Bird Island

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Frequently asked questions

How much does a Two Boats vacation package cost?
You'll find cheap prices from $427 on Expedia for your Two Boats escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Two Boats costs.
What are the cheapest months to go to Two Boats?
To score cheap Two Boats vacation packages, organize your trip outside of peak times such as school holidays. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Two Boats?
The ideal length for your Two Boats vacation depends on what you'd like to do. Usually, a handful of days to a week will give you time to go to all the main attractions and explore some hidden spots along the way.
How to find the best Two Boats package deals?
Bagging a cheap Two Boats package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, add a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Two Boats package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Two Boats vacation as a package?
An Expedia vacation package could land you great savings when compared to booking hotels and flights individually. Better still, you can personalize your Two Boats trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Two Boats?
If you're considering a spontaneous Two Boats vacation, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Two Boats vacation packages?
Secure your dream trip to Two Boats with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait for your next paycheck — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.