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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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.
The price is ￥13,501
￥28,119 total
includes taxes & fees
Oct 20 - Oct 21
Private Loft at a Working Show Barn ~ Pets Welcome!
A bedroom with a bed, nightstands, a ceiling fan, and a window with blinds.

2. 1BR King Suite - Pool, Gym, Games & Dog Friendly

1BR King Suite - Pool, Gym, Games & Dog Friendly
Middleburg
The price is ￥9,727
￥37,511 total
includes taxes & fees
Oct 8 - Oct 9
1BR King Suite - Pool, Gym, Games & Dog Friendly
A gym with treadmills, weight machines, and a bench.

3. 2BR Suite - Pool, Gym, Games & Dog Friendly

2BR Suite - Pool, Gym, Games & Dog Friendly
Middleburg
The price is ￥15,159
￥45,359 total
includes taxes & fees
Nov 2 - Nov 3
2BR Suite - Pool, Gym, Games & Dog Friendly
A pool table with balls, a ceiling fan, a fireplace, and a seating area with a TV.

4. 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.
The price is ￥24,302
￥60,146 total
includes taxes & fees
Oct 8 - Oct 9
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.

5. 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.
The price is ￥25,266
￥51,558 total
includes taxes & fees
Oct 9 - Oct 10
Country living at its best!
A tent with a table and chairs, surrounded by patterned rugs and a wooden deck.

6. Pasture Bedtime Yurt

Pasture Bedtime Yurt
Middleburg
The price is ￥39,083
￥49,022 total
includes taxes & fees
Oct 20 - Oct 21
Pasture Bedtime Yurt
A cozy interior of a tent with a bed, a sofa, a table with a radio, and a refrigerator.

7. Moo-Tel Yurt

Moo-Tel Yurt
Middleburg
The price is ￥39,083
￥49,022 total
includes taxes & fees
Oct 8 - Oct 9
Moo-Tel Yurt
A modern building with a storefront labeled "STUDIORES" and the number "8045".

8. StudioRes by Marriott Jacksonville Orange Park

StudioRes by Marriott Jacksonville Orange Park
3.0 star property
Westside
8.6 out of 10, Excellent, (52 reviews)
"Very roomy, clean, and quite room."
United States
Richard
The price is ￥12,001
￥13,621 total
includes taxes & fees
Oct 12 - Oct 13
StudioRes by Marriott Jacksonville Orange Park
A house entrance with a red door, a welcome mat, and a doormat.

9. 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.
The price is ￥19,314
￥54,218 total
includes taxes & fees
Oct 19 - Oct 20
Luxurious Home w/ Spectacular Glass Room & Patios
A modern hotel room with two beds, white bedding, and a yellow throw blanket.

10. 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.
The price is ￥10,375
￥22,103 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Private Entire Studio Suite Independent Guest Entrance
A swimming pool with lounge chairs, palm trees, and a building in the background.

11. 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.
The price is ￥11,843
￥31,992 total
includes taxes & fees
Oct 13 - Oct 14
Suite Peace- New luxury apartment near NAS JAX and Orange park
A hotel room with two beds, a blue armchair, a small round ottoman, a kitchenette, and a bathroom.

12. 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.
The price is ￥13,107
￥26,100 total
includes taxes & fees
Oct 11 - Oct 12
Cozy Private Tiny Guest House
A conservatory with a glass roof, a potted plant, and a bench.

13. 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.
The price is ￥28,424
￥74,265 total
includes taxes & fees
Oct 8 - Oct 9
Single house: 12guests,4bds/2baths,large backyard.
A covered patio with a table and chairs, a window, and a door.

14. 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.
The price is ￥31,898
￥67,704 total
includes taxes & fees
Oct 12 - Oct 13
Rustic Owl w/ 2Kings In Fleming Island
A modern kitchen with white cabinets, granite countertops, stainless steel appliances, and pendant lighting.

15. ⭐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.
The price is ￥17,665
￥47,347 total
includes taxes & fees
Oct 12 - Oct 13
⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown
A bedroom with a large window, a bed, an orange armchair, and a dresser.

16. New Floating Luxury: Unique Houseboat Retreat

New Floating Luxury: Unique Houseboat Retreat
Orange Park
9.4 out of 10, Exceptional, (33 reviews)
"Front seat views to the daily sunsets over the lake were perfect. Very clean. The bed upstairs was comfortable."
United States
Kim B.
New Floating Luxury: Unique Houseboat Retreat
A kitchen with a sink, a microwave, and cabinets.

17. The Humming Bird Suite - Affordable Lakefront Fun

The Humming Bird Suite - Affordable Lakefront Fun
3.0 star property
Keystone Heights
The price is ￥12,633
￥19,428 total
includes taxes & fees
Oct 8 - Oct 9
The Humming Bird Suite - Affordable Lakefront Fun
A living room with a brick fireplace, a blue armchair, a wooden cabinet, and a ceiling fan.

18. The Van Zant House

The Van Zant House
3.5 star property
Westside
6.4 out of 10, (7 reviews)
"Always a great time ! "
United States
Katherine
The price is ￥10,354
￥43,388 total
includes taxes & fees
Nov 4 - Nov 5
The Van Zant House
A living room with a sofa, coffee table, TV, fireplace, and a dining area in the background.

19. 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.
The price is ￥28,424
￥75,844 total
includes taxes & fees
Oct 9 - Oct 10
Sunset near the lake up to 12 guests,4bds,2baths
A dining table set with a vase of blue flowers, plates, and cutlery.

20. Cozy Treetop Hideaway

Cozy Treetop Hideaway
Northwest
10.0 out of 10, Exceptional, (107 reviews)
"Good location, nice amenities"
United States
Sue
The price is ￥13,501
￥24,755 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Treetop Hideaway
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

Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station

Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station

10/10 Excellent
"Very clean in all areas. The staff was nice and very informative. The breakfast was great and was kept clean as people had eaten and left. She was also nice. The air conditioning worked great! All in all, this was a great place to stay! Will definitely book again!!"
Mercy 1-night trip
Posted 5 hours ago
Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station

Find out more about Middleburg

Search for holiday rentals in Middleburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Middleburg using one of the methods below:

  • View our selection of featured holiday rentals in Middleburg
  • Use the map to find apartments and other holiday homes in the Middleburg neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middleburg while they last

Look no further and take a look at our great range of rental properties in Middleburg!

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.