Jennings Vacations from $2,029

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Your Jennings Vacation

Pick a Jennings vacation package and focus on what matters — having fun. No more planning headaches, just a lot more free time to immerse yourself in the best parts of this fascinating city, such as its rich history and friendly locals. If your trip to Jennings includes some sightseeing, check out renowned attractions like Hermitage Bay, Valley Church Beach and Darkwood Beach. A few quick clicks is all it takes to craft a tailored Jennings vacation on Expedia.

The Latest Jennings vacation packages

Price found within the past 48 hours. Click for updated prices.
Wild Lotus Villa - Waterfront on Jolly Harbour

Wild Lotus Villa - Waterfront on Jolly Harbour

3.5 out of 5
Price was $2,320, price is now $2,029 per person
$2,029
per person
Nov 22 - Nov 29
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to St. John's (ANU)
No reviews
COCOS Hotel - Adults Only - Caters to Couples - All Inclusive

COCOS Hotel - Adults Only - Caters to Couples - All Inclusive

4 out of 5
Save 100% on your flight
Price was $4,603, price is now $2,799 per person
$2,799
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. John's (ANU)
9.4/10 Exceptional! (764 reviews)
Beach, restaurant and balcony views are out of this world. The rooms were lovely and the outdoor shower was very cool and romantic. Great service from the whole resort, the wait staff and bartenders were excellent.

Reviewed on Sep 28, 2025

Galley Bay Resort & Spa

Galley Bay Resort & Spa

5 out of 5
Five Islands Village
Save 100% on your flight
Price was $6,216, price is now $4,126 per person
$4,126
per person
Jan 5 - Jan 10
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to St. John's (ANU)
9.4/10 Exceptional! (457 reviews)
Very good well maintained hotel with lovely gardens. Views from beachfront rooms stunning with good wifi and facilities. Staff excellent, very friendly and attentive. Food and drink all very good especially Ismay restaurant which you pay a supplement for but well worth it.

Reviewed on Oct 23, 2025

Villa Papillon

Villa Papillon

3.5 out of 5
Save 100% on your flight
Price was $15,345, price is now $11,942 per person
$11,942
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. John's (ANU)
No reviews
Ocean Point Beach Resort & Spa - Adults Only

Ocean Point Beach Resort & Spa - Adults Only

4 out of 5
Price was $2,425, price is now $2,042 per person
$2,042
per person
Dec 16 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. John's (ANU)
8.6/10 Excellent! (590 reviews)
Staff are very friendly. I have been here a couole times before and the dining options have improved greatly.

Reviewed on Sep 8, 2025

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Discover the most popular places to visit in Jennings

Hermitage Bay

4.5/5(49 reviews)

Explore the waterfront of Hermitage Bay and enjoy other activities such as boating in Jennings. Amble around this romantic area's beautiful beaches and enjoy its top-notch restaurants.

Hermitage Bay

What to do in Jennings

Horseback Riding at Sandy Beach in Antigua

Horseback Riding at Hawksbill Beach in Five islands Antigua

$120
per adult
Horseback Riding at Hawksbill Beach in Five islands Antigua
Power 360 Catamaran Cruise Antigua

Power 360 Catamaran Cruise Antigua

$148
per adult
92% of travellers recommend
Power 360 Catamaran Cruise Antigua
Turtle Beach Power Snorkeling Adventure

Turtle Beach Power Snorkeling Adventure

$125
per adult
94% of travellers recommend
Turtle Beach Power Snorkeling Adventure
See all activities in Jennings

Jennings Hotel Deals

Hermitage Bay - All Inclusive

Hermitage Bay - All Inclusive

4.5 out of 5
Hermitage Bay, Jennings New Extension, Jennings, Saint Mary
$2,469 nightly
The price is $2,863 total per night from Oct 26 to Oct 27
$2,863 total
Oct 26 - Oct 27
Total with taxes and fees
9.8/10 Exceptional! (32 reviews)
Outstanding

Reviewed on Aug 24, 2025

Hermitage Bay - All Inclusive
Royalton CHIC Antigua, An Autograph Collection All-Inclusive Resort – Adults Only

Royalton CHIC Antigua, An Autograph Collection All-Inclusive Resort – Adults Only

4.5 out of 5
Halcyon Road, St. John's, Saint John
$392 nightly
The price is $392 total per night from Oct 28 to Oct 29
$392 total
Oct 28 - Oct 29
Total with taxes and fees
7.4/10 Good! (477 reviews)
The beach view was amazing. The staff members were very courteous and very helpful. The bar at the pool side have to do better. They did not have straws for our Pinacolars.

Reviewed on Oct 17, 2025

Royalton CHIC Antigua, An Autograph Collection All-Inclusive Resort – Adults Only
Royalton Antigua, An Autograph Collection All-Inclusive Resort

Royalton Antigua, An Autograph Collection All-Inclusive Resort

4.5 out of 5
Five Islands VIllage, St. John's, Saint John
Fully refundableReserve now, pay when you stay
$370 nightly
The price is $370 total per night from Oct 27 to Oct 28
$370 total
Oct 27 - Oct 28
Total with taxes and fees
7.2/10 Good! (1,006 reviews)
It’s a small resort. Staff was great. Good food at the buffet and restaurants. Kids area kept the kids busy with kids pool, play area and kids play house. The pools were going renovations.

Reviewed on Oct 18, 2025

Royalton Antigua, An Autograph Collection All-Inclusive Resort
See all 904 properties in Jennings
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 Jennings Vacation Packages

Jennings Essential Information

Language
English
Currency
East Caribbean dollars
Closest Airport
V.C. Bird Intl. Airport (ANU)
Max Temp Winter
80ºF
Max Temp Summer
80ºF
Top Sights
Valley Church Beach, Fryes Beach and Carlisle Bay Beach

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Frequently asked questions

How much does a Jennings vacation package cost?
You can grab a vacation package to this top destination from $2,029 on Expedia. But how much your vacation to Jennings costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Jennings?
You can usually find lower prices and greater availability in September, October and December. Browse our cheap Jennings vacation packages and you could score some great off-season discounts.
How many days is enough for Jennings?
The ideal length of your Jennings vacation depends on what you'd like to see. Usually, a few days to a week will give you enough time to tick off all the main attractions and explore some hidden gems along the way.
How to find the best Jennings package deals?
Use Expedia's filter tool to find some tempting Jennings package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Jennings package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Jennings vacation as a package?
You can enjoy significant savings on your Jennings break by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Jennings?
Land incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Jennings getaway.
How to plan a trip to Jennings?

  1. Choose your dates: What you want to do in Jennings and your favorite season can help you decide when to go.
  2. Budget wisely: As well as the cost of your hotel, you'll need to factor in other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that may arise during your trip to Jennings.
  3. Organize your Jennings getaway with Expedia's trip planning tool: Search for and book accommodations and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Jennings together.
  4. Decide your trip length: Consider how long you want to spend discovering Jennings. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Jennings vacation package that brings all your bookings together.
  6. Book experiences or activities ahead of time: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on the best Jennings has to offer. Find all the incredible things to do in Jennings with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Jennings vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Jennings trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.