Middleburg Vacations from $356

Book a Hotel + Flight or Car together to unlock savings

Photo by Cindy Simmonds

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Middleburg vacation packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Jacksonville Beach

Margaritaville Jacksonville Beach

2.5 out of 5
Price was $503, price is now $356 per person
$356
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
9/10 Wonderful! (3,345 reviews)
Everything was great, beautiful property!!!

Reviewed on Dec 13, 2025

Amelia by the South

Amelia by the South

4 out of 5
Save 100% on your flight
Price was $5,413, price is now $3,358 per person
$3,358
per person
Feb 15 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
No reviews
Amelia by the Sea

Amelia by the Sea

4 out of 5
Save 100% on your flight
Price was $5,440, price is now $3,385 per person
$3,385
per person
Feb 15 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
No reviews
Omni Amelia Island Resort & Spa

Omni Amelia Island Resort & Spa

4 out of 5
Save 100% on your flight
Price was $783, price is now $560 per person
$560
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
8.8/10 Excellent! (1,003 reviews)
The room was beautifully cleaned all the amenities you could want were there. The people were incredibly helpful at the hotel and super friendly!

Reviewed on Nov 21, 2025

Hilton Jacksonville At Mayo Clinic

Hilton Jacksonville At Mayo Clinic

4.5 out of 5
Save 100% on your flight
Price was $796, price is now $570 per person
$570
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
9.4/10 Exceptional! (22 reviews)
Very clean nice rooms! Beds are terrible. It’s like someone slept on one side of the bedroom for 20 years without turning the bed….it goes uphill from one side to the other! Very nice room though with great facilities!

Reviewed on Dec 12, 2025

Don't see what you're looking for?
See all available trips from Columbus to Middleburg
View all trips

Middleburg Hotel Deals

Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
225 E Coastline Dr Jacksonville FL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $165 total per night from Dec 21 to Dec 22
$165 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (1,374 reviews)
Loved

Reviewed on Dec 8, 2025

Hyatt Regency Jacksonville
Embassy Suites by Hilton Jacksonville Baymeadows

Embassy Suites by Hilton Jacksonville Baymeadows

3.5 out of 5
9300 Baymeadows Road Jacksonville FL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $135 total per night from Dec 21 to Dec 22
$135 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (1,277 reviews)
Clean room... Friendly staff and great breakfast. Loved the happy hour drinks were great.

Reviewed on Dec 8, 2025

Embassy Suites by Hilton Jacksonville Baymeadows
DoubleTree by Hilton Hotel Jacksonville Riverfront

DoubleTree by Hilton Hotel Jacksonville Riverfront

4 out of 5
1201 Riverplace Boulevard Jacksonville FL
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $103 total per night from Dec 21 to Dec 22
$103 total
Dec 21 - Dec 22
Total with taxes and fees
6.6/10 (1,468 reviews)
View was beautiful

Reviewed on Dec 7, 2025

DoubleTree by Hilton Hotel Jacksonville Riverfront
See all 1,802 properties in Middleburg
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 Middleburg Vacation Packages

Middleburg Essential Information

Language
English
Currency
U.S dollars
Population
13,000
Max Temp Winter
70ºF
Max Temp Summer
95ºF
Top Sights
Spring Park and Clay County Fairgrounds

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Middleburg vacation package cost?
You can snap up a vacation package to this top destination from $356 on Expedia. But how much your vacation to Middleburg costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Middleburg?
You can usually find lower prices and better availability in December, January and February. Explore our cheap Middleburg vacation packages and you could score some excellent off-season deals.
How many days is enough for Middleburg?
Usually, a handful of days is enough to see the top attractions during your Middleburg vacation. But if you prefer to have time to unwind or take day tours, think about extending your trip.
How to find the best Middleburg package deals?
Use Expedia's filters to help you find some of the best Middleburg package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Middleburg package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middleburg vacation as a package?
You can enjoy significant savings on your Middleburg getaway by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Middleburg?
If you're considering a spur-of-the-moment Middleburg trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Middleburg vacation packages?
If you're like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Middleburg trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

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