Middleburg Vacations from $390

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The Latest Middleburg vacation packages

Price found within the past 48 hours. Click for updated prices.
Delta Hotels by Marriott™ Jacksonville Deerwood

Delta Hotels by Marriott™ Jacksonville Deerwood

4 out of 5
Southside
Save 100% on your flight
Price was $572, price is now $390 per person
$390
per person
Jan 28 - Feb 3
just found
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
8.6/10 Excellent! (432 reviews)
Very helpful and polite reception by “ Gigi”

Reviewed on Dec 22, 2025

Amelia by the South

Amelia by the South

4 out of 5
Price was $5,454, price is now $3,113 per person
$3,113
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 $5,412, price is now $3,140 per person
$3,140
per person
Feb 15 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
No reviews
Tricove Inn & Suites

Tricove Inn & Suites

2.5 out of 5
Southside
Save 100% on your flight
Price was $697, price is now $425 per person
$425
per person
Mar 1 - Mar 8
just found
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
7.2/10 Good! (1,000 reviews)
Affordable and close to the interstate.

Reviewed on Oct 13, 2025

Landing Apartments Jacksonville - Southside

Landing Apartments Jacksonville - Southside

3 out of 5
Southside
Save 100% on your flight
Price was $1,056, price is now $727 per person
$727
per person
Mar 1 - Mar 8
just found
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
No reviews
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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
$149 nightly
The price is $170 total per night from Jan 1 to Jan 2
$170 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.8/10 Excellent! (1,395 reviews)
Very clean

Reviewed on Dec 18, 2025

Hyatt Regency Jacksonville
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
$124 nightly
The price is $141 total per night from Dec 28 to Dec 29
$141 total
Dec 28 - Dec 29
Total with taxes and fees
6.6/10 (1,487 reviews)
The view was beautiful, room was clean, staff was friendly

Reviewed on Dec 18, 2025

DoubleTree by Hilton Hotel Jacksonville Riverfront
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
$106 nightly
The price is $120 total per night from Dec 30 to Dec 31
$120 total
Dec 30 - Dec 31
Total with taxes and fees
8.4/10 Very Good! (1,294 reviews)
The breakfast was good! And I enjoyed the king suite.

Reviewed on Dec 20, 2025

Embassy Suites by Hilton Jacksonville Baymeadows
See all 1,797 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

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Frequently asked questions

How much does a Middleburg vacation package cost?
You can snap up a vacation package to this top destination from $390 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.

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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.