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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Middleburg holiday homes

A rustic building with a wooden staircase leading to a deck, a covered area with a sign reading "GRAND LANDINGS," and outdoor seating.

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)
"Tracy was a great host I enjoyed talking with her. The loft was great the beds are comfortable very clean and has everything you need for a short or long stay I will definitely be back and this would be my first choice to stay at."
United States
Tina S.
The price is HK$671
HK$1,397 total
includes taxes & fees
29 Oct - 30 Oct
Private Loft at a Working Show Barn ~ Pets Welcome!
A modern kitchen with white cabinetry, a large island, stainless steel appliances, and pendant lighting.

2. 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, (4 reviews)
"Great place! Highly recommend"
United States
Nyle K.
The price is HK$1,207
HK$2,988 total
includes taxes & fees
1 Nov - 2 Nov
NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
A cozy interior with a wooden ceiling, a brown leather sofa, a world map on the wall, and a sliding glass door.

3. Tiny Farm: Charming Tiny House in the Country

Tiny Farm: Charming Tiny House in the Country
Green Cove Springs
The price is HK$635
HK$872 total
includes taxes & fees
29 Oct - 30 Oct
Tiny Farm: Charming Tiny House in the Country
A house entrance with a red door, a welcome mat, and a doormat.

4. Luxurious Home w/ Spectacular Glass Room & Patios

Luxurious Home w/ Spectacular Glass Room & Patios
Lakeside
9.8 out of 10, Exceptional, (186 reviews)
"Thank you for a wonderful stay!"
United States
Katherine B.
The price is HK$960
HK$2,702 total
includes taxes & fees
1 Nov - 2 Nov
Luxurious Home w/ Spectacular Glass Room & Patios
A modern kitchen with stainless steel appliances, granite countertops, and dark wood cabinetry.

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

The Trail & Tide House, Beaches, Trails, Hikes
Lakeside
10.0 out of 10, Exceptional, (1 review)
"The home was clean and spacious. There is not a lot of furniture but we only needed the bedrooms. The beds were comfortable and the linens were clean and high quality. The home is in a nice neighborhood and felt very secure."
United States
Brian K.
The price is HK$1,112
HK$2,659 total
includes taxes & fees
29 Oct - 30 Oct
The Trail & Tide House, Beaches, Trails, Hikes
A conservatory with a glass roof, a potted plant, and a bench.

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

Single house: 12guests,4bds/2baths,large backyard.
Jacksonville
9.8 out of 10, Exceptional, (50 reviews)
"Great place for big families and small children. "
United States
Maria R.
The price is HK$1,412
HK$3,962 total
includes taxes & fees
29 Oct - 30 Oct
Single house: 12guests,4bds/2baths,large backyard.
A covered patio with a table and chairs, a window, and a door.

7. Rustic Owl w/ 2Kings In Fleming Island

Rustic Owl w/ 2Kings In Fleming Island
Fleming Island
9.8 out of 10, Exceptional, (43 reviews)
"Great location. Property was well stocked, clean and comfortable."
United States
Joe T.
The price is HK$1,585
HK$3,364 total
includes taxes & fees
15 Nov - 16 Nov
Rustic Owl w/ 2Kings In Fleming Island
A modern living space with a dining area, sofa, kitchen, and a TV displaying a show.

8. Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths

Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths
Orange Park
9.4 out of 10, Exceptional, (3 reviews)
"It will be very difficult to convince mate other places to this beautiful rental. The pool was huge and clean the property had everything we needed. Would surely stay again!! The host was easily to access"
United States
BILLIE
The price is HK$2,609
HK$5,722 total
includes taxes & fees
29 Oct - 30 Oct
Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths
A modern kitchen with a central island, stainless steel appliances, and a dining area with a marble floor.

9. Enjoyable 3-bedroom house with pool and AC in charming Jacksonville, Florida.

Enjoyable 3-bedroom house with pool and AC in charming Jacksonville, Florida.
Westside
6.0 out of 10, (2 reviews)
"My family and I loved the place very clean and comfortable and the host was excellent with getting back in touch with me when I reached out"
United States
Anonymous traveller
The price is HK$1,271
HK$3,390 total
includes taxes & fees
31 Oct - 1 Nov
Enjoyable 3-bedroom house with pool and AC in charming Jacksonville, Florida.
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, and a view of the outdoors through a sliding glass door.

10. Spacious 3 BR Near NAS Jax l BBQ, WiFi, DirecTV

Spacious 3 BR Near NAS Jax l BBQ, WiFi, DirecTV
Westside
7.0 out of 10, Good, (2 reviews)
"The location was surprisingly amazing—we really enjoyed our time sitting out back. It was so quiet and peaceful, perfect for relaxing. I would definitely recommend this place to anyone looking for a calm and comfortable stay."
United States
Jennifer B.
The price is HK$815
HK$2,106 total
includes taxes & fees
29 Oct - 30 Oct
Spacious 3 BR Near NAS Jax l BBQ, WiFi, DirecTV
A living room with a sofa, coffee table, TV, fireplace, and a dining area in the background.

11. 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 HK$1,553
HK$3,944 total
includes taxes & fees
29 Oct - 30 Oct
Sunset near the lake up to 12 guests,4bds,2baths
A living room with a dark grey sofa, a coffee table, a flat-screen TV, and a large window with blinds.

12. Spacious Retreat: Projector & Pool Table

Spacious Retreat: Projector & Pool Table
Westside
9.8 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay. No problems. Highly recommend. "
United Kingdom
Thomas K.
The price is HK$698
HK$2,691 total
includes taxes & fees
1 Nov - 2 Nov
Spacious Retreat: Projector & Pool Table
A wooden porch leading to a house with a front door, a lamp, and a doormat.

13. Gorgeous circa 1875 Plantation House (in city)

Gorgeous circa 1875 Plantation House (in city)
Orange Park
9.8 out of 10, Exceptional, (97 reviews)
"Our families enjoyed this lovely home. Everything is clean, the beds are comfy, plenty of towels and a well equipped kitchen. The grounds are lovely and well kept. Although it was a little too warm to sit outside, there were several inviting areas on the wrap around shaded porch. The host is very congenial and responsive. We would stay here again."
United States
Cheryl A.
The price is HK$1,137
HK$3,634 total
includes taxes & fees
9 Nov - 10 Nov
Gorgeous circa 1875 Plantation House (in city)
A grand staircase with white balusters and wooden steps leading to an upper level.

14. 30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs

30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
Fleming Island
9.2 out of 10, Wonderful, (34 reviews)
"A beautifully decorated, comfortable, and spacious property.The back porch was our favorite place to gather for visiting and viewing the canal activities. It has a claw footed tub in the Jack and Jill bathroom. A large game room is on the second floor. Also many extra beds are available. The kitchen is well appointed with every possible need close at hand."
United States
Carol G.
The price is HK$4,413
HK$12,406 total
includes taxes & fees
29 Oct - 30 Oct
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
A modern kitchen with dark wood cabinets, a stainless steel refrigerator, and a built-in sink with a dish rack.

15. Home Theater, Kayaks & EV Charger in Ortega

Home Theater, Kayaks & EV Charger in Ortega
Westside
9.0 out of 10, Wonderful, (2 reviews)
"Property was very nice and clean. Tyler was a great help. Shower was the only kinda let down of our stay"
United States
Darrick S.
The price is HK$644
HK$2,395 total
includes taxes & fees
1 Nov - 2 Nov
Home Theater, Kayaks & EV Charger in Ortega
A living room with a sectional sofa, a wooden coffee table, a bookshelf, and a painting on the wall.

16. Charming Animal-Themed Family Stay

Charming Animal-Themed Family Stay
Westside
10.0 out of 10, Exceptional, (2 reviews)
"This is a host who NEVER disappoints!! My family and I stayed at one of his other listings and it was amazing so I knew this was going to be the same experience! Located on the Westside of Jacksonville means you will be close to everything and more! The animal theme in the house was great, hot hot water for the shower and comfy bed! Not overly decorative but felt like home. I could go on forever but if you're looking for comfort, safety and relaxation this is your home! Thank you Geoff and Kat...
United States
Carla B.
The price is HK$832
HK$2,240 total
includes taxes & fees
29 Oct - 30 Oct
Charming Animal-Themed Family Stay
A living room with a sofa, armchairs, a coffee table, a fireplace, and a window with curtains.

17. Park Street Paradise 2BR Cottage

Park Street Paradise 2BR Cottage
Westside
The price is HK$760
HK$2,801 total
includes taxes & fees
2 Nov - 3 Nov
Park Street Paradise 2BR Cottage
A covered porch with red chairs and a table, brick pillars, and a view of the neighborhood.

18. Spacious Murray Hill Getaway for One or Two

Spacious Murray Hill Getaway for One or Two
Northwest
10.0 out of 10, Exceptional, (4 reviews)
"Loved the location to shops near by with plenty of options. Stay was cozy and the extra rags on top of the refrigerator was super helpful for cleanup. I would love to stay here again! My kid loved it too "
United States
dahlia t.
The price is HK$628
HK$1,798 total
includes taxes & fees
3 Nov - 4 Nov
Spacious Murray Hill Getaway for One or Two
A small house with a fenced backyard, a patio with red chairs, and a garden with a potted plant.

19. Stylish Bungalow Near Dining, Parks & Entertainment

Stylish Bungalow Near Dining, Parks & Entertainment
Avondale
10.0 out of 10, Exceptional, (17 reviews)
"great place and host! "
United States
Savannah F.
The price is HK$812
HK$1,524 total
includes taxes & fees
30 Oct - 31 Oct
Stylish Bungalow Near Dining, Parks & Entertainment
A room with two beds, a wooden desk, a chair, a bookshelf, and a door.

20. Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL

Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
Northwest
10.0 out of 10, Exceptional, (47 reviews)
"Great place to stay"
United States
Summer I.
The price is HK$902
HK$1,493 total
includes taxes & fees
29 Oct - 30 Oct
Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
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

Hyatt Place Jacksonville / St. Johns Town Center

Hyatt Place Jacksonville / St. Johns Town Center

10/10 Excellent
"10/10"
Eddie 1-night trip
Posted 1 hour ago
Hyatt Place Jacksonville / St. Johns Town Center

Find out more about Middleburg

Middleburg Vacation Homes information

Number of reviews
523
Accommodation
647 Vacation Homes
Lowest Price
HK$872
Highest Price
HK$12,406

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