Photo by Cindy Simmonds

Middleburg Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
14 Dec - 15 Dec
Tomorrow
15 Dec - 16 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Our top choices for Middleburg holiday rentals

Exterior
Private Loft at a Working Show Barn ~ Pets Welcome!

Holiday Home in Middleburg

Private Loft at a Working Show Barn ~ Pets Welcome!
9.6 out of 10, Exceptional, (22)
"We were in town for our oldest grandson's graduation. Our younger grandsons loved coming to see the horses and learning about them. This property is perfectly located, convenient to everything, yet quiet and private. Perfect stay, will be back when visiting in the future!"
United States
Susan G.
The price is HK$740
HK$1,469 total
includes taxes & fees
6 Jan - 7 Jan 2026
Private Loft at a Working Show Barn ~ Pets Welcome!
Terrace/patio
Country living at its best!

Mobile Home in Middleburg

Country living at its best!
9.0 out of 10, Wonderful, (2)
"We spent one night with our dogs the property is fabulous quiet and wide open space . Home is clean and lots of space I would recommend this property "
United States
Kris C.
The price is HK$1,246
HK$2,542 total
includes taxes & fees
30 Dec - 31 Dec
Country living at its best!
Property grounds
Nomad RV #1

Mobile Home in Westside

Nomad RV #1
The price is HK$669
HK$1,887 total
includes taxes & fees
13 Jan - 14 Jan 2026
Nomad RV #1
Property grounds
Cozy RV with AC and WiFi in Terrific Melrose

Mobile Home in Melrose

Cozy RV with AC and WiFi in Terrific Melrose
The price is HK$413
HK$787 total
includes taxes & fees
15 Dec - 16 Dec
Cozy RV with AC and WiFi in Terrific Melrose
Outdoor dining
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing

Cottage in Keystone Heights

White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
2.0 star property
9.6 out of 10, Exceptional, (14)
"Awesome location, great cabin! Had everything I needed to see my family ❤️ Will request to stay again!"
United States
Bonnie
The price is HK$343
HK$1,199 total
includes taxes & fees
15 Dec - 16 Dec
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
Outdoor dining
Colorful Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL

Holiday Home in Northwest

Colorful Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
9.8 out of 10, Exceptional, (31)
"Relazing weekend, nice property!"
United States
Michelle M.
The price is HK$876
HK$1,282 total
includes taxes & fees
15 Dec - 16 Dec
Colorful Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
Fridge, microwave, oven, stovetop
Central 2BR Near Mayo Clinic with Fenced Yard and Patio!

Holiday Home in Southside

Central 2BR Near Mayo Clinic with Fenced Yard and Patio!
2.0 star property
9.6 out of 10, Exceptional, (5)
"Location was perfect, house was exactly as advertised and was just right for our needs. Will definitely stay here again if we return to Jacksonville. "
United States
Steven Z.
Central 2BR Near Mayo Clinic with Fenced Yard and Patio!
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy Private Entire Studio Suite Independent Guest Entrance

Apartment in Westside

Cozy Private Entire Studio Suite Independent Guest Entrance
9.8 out of 10, Exceptional, (17)
"Nice place to chill out before you go on vacation cruise. "
United States
Christopher W.
The price is HK$511
HK$1,090 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Private Entire Studio Suite Independent Guest Entrance
Property grounds
Cozy Treetop Hideaway

Apartment in Northwest

Cozy Treetop Hideaway
10.0 out of 10, Exceptional, (84)
"Such a lovely little apartment. Very clean too. Daiv was a wonderful host. "
United States
S F.
The price is HK$560
HK$1,101 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Treetop Hideaway
Property grounds
Riverfront House With Breathtaking Views, Grill, King Bed, Near Jaguars Stadium!

Holiday Home in Northwest

Riverfront House With Breathtaking Views, Grill, King Bed, Near Jaguars Stadium!
10.0 out of 10, Exceptional, (8)
"Great place to stay! Just like it advertised! Fun and peaceful"
United States
Angela R.
The price is HK$615
HK$2,048 total
includes taxes & fees
16 Dec - 17 Dec
Riverfront House With Breathtaking Views, Grill, King Bed, Near Jaguars Stadium!
Terrace/patio
Bright Airy Luxurious Abode in Walkable Riverside

Apartment in Northwest

Bright Airy Luxurious Abode in Walkable Riverside
9.4 out of 10, Exceptional, (3)
"Place was clean, comfortable. We enjoyed the outside space also. Peaceful "
United States
Geralyn G.
The price is HK$545
HK$1,105 total
includes taxes & fees
15 Dec - 16 Dec
Bright Airy Luxurious Abode in Walkable Riverside
Fridge, microwave, oven, stovetop
AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin

Holiday Home in Del Rio

AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin
10.0 out of 10, Exceptional, (44)
"This was an overnight stop. Great location, easy to get back on the road. Nice fenced yard, spacious home, quiet neighborhood!We will be staying here again."
United States
Richard G.
The price is HK$771
HK$2,153 total
includes taxes & fees
16 Dec - 17 Dec
AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin
1 bedroom, desk, iron/ironing board, WiFi
Magical Midsummer Night Glamping Loft w Bikes

Apartment in Northwest

Magical Midsummer Night Glamping Loft w Bikes
2.0 star property
10.0 out of 10, Exceptional, (5)
"The property was great & in a good location. It was very nicely decorated and was in excellent condition. It was updated completely & very well taken care of by owners. The garden was very nice. The only problem I had was the stairs - I’m almost 70 & had a little trouble. I wouldn’t recommend for elderly & handicap persons. "
United States
Frances
The price is HK$529
HK$1,088 total
includes taxes & fees
15 Dec - 16 Dec
Magical Midsummer Night Glamping Loft w Bikes
Pool
Golfside Getaway | Pool • Hot Tub • Gym Access

Condo in Saint Augustine

Golfside Getaway | Pool • Hot Tub • Gym Access
9.6 out of 10, Exceptional, (8)
"Great place. We stay every time we come to Florida "
United States
Wendell W.
Golfside Getaway | Pool • Hot Tub • Gym Access
Fridge, microwave, oven, stovetop
Cozy Riverside Villa - Walk to Bars & Restaurants!

Holiday Home in Northwest

Cozy Riverside Villa - Walk to Bars & Restaurants!
9.4 out of 10, Exceptional, (13)
"Great stay here - clean, well maintained and well managed"
United States
Duane C.
The price is HK$662
HK$2,886 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Riverside Villa - Walk to Bars & Restaurants!
Interior
Enchanted Forest: a Magical Luxury Studio

Apartment in Northwest

Enchanted Forest: a Magical Luxury Studio
10.0 out of 10, Exceptional, (3)
"The room was excellent. The ambience was perfect. I would stay again for sure "
United States
Timothy B.
The price is HK$631
HK$1,195 total
includes taxes & fees
5 Jan - 6 Jan 2026
Enchanted Forest: a Magical Luxury Studio
Property grounds
Cozy Hideaway in Jacksonville

Apartment in Arlington

Cozy Hideaway in Jacksonville
7.6 out of 10, Good, (27)
"It was nice and cozy"
United States
Brandon G.
The price is HK$420
HK$831 total
includes taxes & fees
16 Dec - 17 Dec
Cozy Hideaway in Jacksonville
A heated pool
Beautiful 1 bedroom condo in World Golf Village King and Bear St. Augustine

Condo in St. Augustine

Beautiful 1 bedroom condo in World Golf Village King and Bear St. Augustine
9.6 out of 10, Exceptional, (32)
"Very roomy. Clean. Great pool. Near King and Bear golf course."
United States
Ann T.
The price is HK$740
HK$2,383 total
includes taxes & fees
15 Dec - 16 Dec
Beautiful 1 bedroom condo in World Golf Village King and Bear St. Augustine
Front of property
Chic Farm Glamping Exclusive Perks

Cottage in Melrose

Chic Farm Glamping Exclusive Perks
3.0 star property
The price is HK$1,094
HK$2,048 total
includes taxes & fees
15 Dec - 16 Dec
Chic Farm Glamping Exclusive Perks
Exterior
The Water Oak Bungalow quaint and cozy Murray Hill Riverside Home close downtown

Holiday Home in Northwest

The Water Oak Bungalow quaint and cozy Murray Hill Riverside Home close downtown
9.6 out of 10, Exceptional, (19)
"Jesika was a very accommodating host. I needed to change our booking several times, and she was really responsive and helpful. The property was comfy and we enjoyed our stay so much."
United States
Susan F.
The price is HK$724
HK$2,090 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Water Oak Bungalow quaint and cozy Murray Hill Riverside Home close 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middleburg Hotel Reviews

Homewood Suites by Hilton Jacksonville-South/St. Johns Ctr.

Homewood Suites by Hilton Jacksonville-South/St. Johns Ctr.

10/10 Excellent
"Good service. Clean"
Aileen 2-night trip
Posted 1 day ago
Homewood Suites by Hilton Jacksonville-South/St. Johns Ctr.

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 holiday rentals in Middleburg?

Yes, there are holiday rentals close to the most popular sights in Middleburg, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Middleburg has to offer?

Cozy House close To Downtown: This holiday home rental outside of Middleburg offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family.

How many holiday rentals are there in Middleburg?

Expedia has 21 holiday rentals for your stay in Middleburg.

What’s there to see and do in Middleburg?

While exploring the area, visit family-friendly sights like Ronnie Van Zant Park, or get outside and enjoy nature at Jennings State Forest. In the wider area, you’ll find Eagle Harbor Golf Club and Clay County Fairgrounds.

What’s a holiday rental in Middleburg like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middleburg. Holiday rentals feature amenities 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 cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.