A sunset over a calm lake with a dock and boats.

Middleburg Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middleburg vacation rentals

A stable with horses, hay bales, and a wooden floor.

1. Private Loft at a Working Show Barn ~ Pets Welcome!

Private Loft at a Working Show Barn ~ Pets Welcome!
Middleburg
9.6 out of 10, Exceptional, (28 reviews)
"Horses were great, stay was wonderful, very relaxing "
United States
Tina S.
$161 nightly
The price is $178
Oct 3 - Oct 4
Total with taxes and fees
Private Loft at a Working Show Barn ~ Pets Welcome!
A restroom with two sinks, white tiled walls, and a black hexagonal floor.

2. 2BR Suite - Pool, Gym, Games & Dog Friendly

2BR Suite - Pool, Gym, Games & Dog Friendly
Middleburg
$218 nightly
The price is $245
Oct 6 - Oct 7
Total with taxes and fees
2BR Suite - Pool, Gym, Games & Dog Friendly
A modern living room with a shuffleboard table, a large flat-screen TV, and a seating area with sofas and ottomans.

3. 1BR King Suite - Pool, Gym, Games & Dog Friendly

1BR King Suite - Pool, Gym, Games & Dog Friendly
Middleburg
$200 nightly
The price is $225
Oct 6 - Oct 7
Total with taxes and fees
1BR King Suite - Pool, Gym, Games & Dog Friendly
A bedroom with a bed, nightstands, a ceiling fan, and patterned wallpaper.

4. 2BR Suite - Pool, Gym, Games & Dog Friendly

2BR Suite - Pool, Gym, Games & Dog Friendly
Middleburg
$239 nightly
The price is $269
Oct 6 - Oct 7
Total with taxes and fees
2BR Suite - Pool, Gym, Games & Dog Friendly
A pool table with balls, a ceiling fan, a fireplace, and a seating area with a TV.

5. NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS

NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
Middleburg
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, lots of space and plenty of places to hang out and lounge. Host communicated promptly and kindly. Highly recommend!"
United States
Brandon T.
$343 nightly
The price is $381
Oct 4 - Oct 5
Total with taxes and fees
NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
A modern kitchen with a stainless steel refrigerator, white cabinets, and a wooden floor.

6. Country living at its best!

Country living at its best!
Middleburg
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay at this quiet, country home. Spacious and renovated interior with a lovely side yard for relaxing in the evening. The host was fabulous and quick to respond to all our questions. We will definitely stay here again. "
United States
Amy M.
$294 nightly
The price is $327
Oct 5 - Oct 6
Total with taxes and fees
Country living at its best!
A tent with a table and chairs, surrounded by patterned rugs and a wooden deck.

7. Pasture Bedtime Yurt

Pasture Bedtime Yurt
Middleburg
$280 nightly
The price is $310
Oct 6 - Oct 7
Total with taxes and fees
Pasture Bedtime Yurt
A cozy interior of a tent with a bed, a sofa, a table with a radio, and a refrigerator.

8. Moo-Tel Yurt

Moo-Tel Yurt
Middleburg
$280 nightly
The price is $310
Oct 4 - Oct 5
Total with taxes and fees
Moo-Tel Yurt
A modern building with a storefront labeled "STUDIORES" and the number "8045".

9. StudioRes by Marriott Jacksonville Orange Park

StudioRes by Marriott Jacksonville Orange Park
3.0 star property
Westside
8.6 out of 10, Excellent, (49 reviews)
"Very roomy, clean, and quite room."
United States
Richard
$76 nightly
The price is $86
Oct 7 - Oct 8
Total with taxes and fees
StudioRes by Marriott Jacksonville Orange Park
A house entrance with a red door, a welcome mat, and a doormat.

10. Luxurious Home w/ Spectacular Glass Room & Patios

Luxurious Home w/ Spectacular Glass Room & Patios
Lakeside
9.8 out of 10, Exceptional, (183 reviews)
"Nice property. The bunk bed mattresses were very uncomfortable and need replacing. The indoor patio was excellent for gathering. We enjoyed our stay"
United States
Cynthia J.
$300 nightly
The price is $334
Oct 7 - Oct 8
Total with taxes and fees
Luxurious Home w/ Spectacular Glass Room & Patios
A hotel room with a bed, a ceiling fan, a mirror, and a door leading to a bathroom.

11. The Trail & Tide House, Beaches, Trails, Hikes

The Trail & Tide House, Beaches, Trails, Hikes
Lakeside
$289 nightly
The price is $322
Oct 4 - Oct 5
Total with taxes and fees
The Trail & Tide House, Beaches, Trails, Hikes
A conservatory with a glass roof, a potted plant, and a bench.

12. Single house: 12guests,4bds/2baths,large backyard.

Single house: 12guests,4bds/2baths,large backyard.
Jacksonville
9.8 out of 10, Exceptional, (49 reviews)
"Great place for big families and small children. "
United States
Maria R.
$429 nightly
The price is $480
Oct 4 - Oct 5
Total with taxes and fees
Single house: 12guests,4bds/2baths,large backyard.
A modern hotel room with two beds, white bedding, and a yellow throw blanket.

13. Cozy Private Entire Studio Suite Independent Guest Entrance

Cozy Private Entire Studio Suite Independent Guest Entrance
Westside
9.4 out of 10, Exceptional, (21 reviews)
"Nice and cozy!!Easy access, clean and comfortable!!Will book again "
United States
Shantrill G.
$126 nightly
The price is $140
Oct 4 - Oct 5
Total with taxes and fees
Cozy Private Entire Studio Suite Independent Guest Entrance
A hotel room with two beds, a blue armchair, a small round ottoman, a kitchenette, and a bathroom.

14. Cozy Private Tiny Guest House

Cozy Private Tiny Guest House
Westside
10.0 out of 10, Exceptional, (1 review)
"There's a gas station nearby. Have to drive a little for groceries and restaurants. The room was excellent in every way. "
United States
Theodore D.
$148 nightly
The price is $165
Oct 2 - Oct 3
Total with taxes and fees
Cozy Private Tiny Guest House
A covered patio with a table and chairs, a window, and a door.

15. Rustic Owl w/ 2Kings In Fleming Island

Rustic Owl w/ 2Kings In Fleming Island
Fleming Island
10.0 out of 10, Exceptional, (41 reviews)
"Great location. Property was well stocked, clean and comfortable."
United States
Joe T.
$386 nightly
The price is $429
Oct 5 - Oct 6
Total with taxes and fees
Rustic Owl w/ 2Kings In Fleming Island
A swimming pool with lounge chairs, palm trees, and a building in the background.

16. Suite Peace- New luxury apartment near NAS JAX and Orange park

Suite Peace- New luxury apartment near NAS JAX and Orange park
Westside
9.4 out of 10, Exceptional, (19 reviews)
"Convenient location. Very comfortable. "
United States
Aimee G.
$198 nightly
The price is $222
Oct 13 - Oct 14
Total with taxes and fees
Suite Peace- New luxury apartment near NAS JAX and Orange park
A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

17. ⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping

⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping
Westside
9.4 out of 10, Exceptional, (16 reviews)
"We came here for work. Place was clean and comfortable. Similar price to a hotel but way more space and comfort. We’ll definitely stay here again if we come back to this area."
United States
Tia J.
$233 nightly
The price is $260
Oct 2 - Oct 3
Total with taxes and fees
⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping
A living room with a sofa, coffee table, TV, fireplace, and a dining area in the background.

18. Sunset near the lake up to 12 guests,4bds,2baths

Sunset near the lake up to 12 guests,4bds,2baths
Westside
10.0 out of 10, Exceptional, (13 reviews)
"great for families "
United States
Dylan A.
$429 nightly
The price is $480
Oct 3 - Oct 4
Total with taxes and fees
Sunset near the lake up to 12 guests,4bds,2baths
A bedroom with a bed, a window, a nightstand, and a wall-mounted projector displaying a green cloud projection.

19. Cosmic Quarters, Whole House, Sleeps 6

Cosmic Quarters, Whole House, Sleeps 6
Westside
9.8 out of 10, Exceptional, (14 reviews)
"House great nice and clean ,family loved it thanks again."
United States
tony s.
$280 nightly
The price is $314
Oct 2 - Oct 3
Total with taxes and fees
Cosmic Quarters, Whole House, Sleeps 6
A modern kitchen with white cabinets, granite countertops, stainless steel appliances, and pendant lighting.

20. ⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown

⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown
Westside
9.4 out of 10, Exceptional, (30 reviews)
"The host was amazing and communicated through the entire stay"
United States
Ebony R.
$268 nightly
The price is $300
Oct 6 - Oct 7
Total with taxes and fees
⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown
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.
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Top Middleburg Hotel Reviews

San Marco Inn East

San Marco Inn East

10/10 Excellent
"Easy location and plenty of parking spaces ."
Eleanor 2-night trip
Posted 19 hours ago
San Marco Inn East

Find out more about Middleburg

Everything you need to know about Middleburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middleburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middleburg vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middleburg vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middleburg. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middleburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $65 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middleburg rentals

At Expedia, we put the best Middleburg vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middleburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middleburg vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middleburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Middleburg?

Yes, you can find vacation rentals close to the most popular sights in Middleburg, or you can go with a secluded option if you're looking for relaxation. Middleburg is known for its shopping and baseball games. Make sure you have time to check out the restaurants and festivals during your trip.

What are some of the best vacation rentals in Middleburg?

Lakefront Home with Outdoor Pool Table, Firepit, and Grill in Jacksonville: This vacation home rental near Middleburg offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table.

How many vacation rentals are there in Middleburg?

Expedia has 23 vacation rentals for your stay in Middleburg.

What’s there to see and do in Middleburg?

Doctors Lake and Jennings State Forest are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Eagle Harbor Golf Club and Clay County Fairgrounds.

What’s a vacation rental in Middleburg like?

A vacation rental is a private property you can stay in for a long or short time in Middleburg. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips.