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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Middleburg vacation homes

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, (27 reviews)
"Horses were great, stay was wonderful, very relaxing "
United States
Tina S.
The price is CA $119
CA $234 total
includes taxes & fees
Sep 28 - Sep 29
Private Loft at a Working Show Barn ~ Pets Welcome!
A covered outdoor area with a wooden deck, wicker furniture, and a table with chairs.

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
The price is CA $214
CA $534 total
includes taxes & fees
Sep 22 - Sep 23
NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
A house entrance with a red door, a welcome mat, and a doormat.

3. 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 CA $263
CA $594 total
includes taxes & fees
Sep 27 - Sep 28
Luxurious Home w/ Spectacular Glass Room & Patios

4. Luxury quite and Comfortable Getaway

Luxury quite and Comfortable Getaway
Middleburg
The price is CA $264
CA $386 total
includes taxes & fees
Sep 22 - Sep 23
Luxury quite and Comfortable Getaway
A dining table with four chairs, a central island, and a tiled floor.

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

The Trail & Tide House, Beaches, Trails, Hikes
Lakeside
The price is CA $196
CA $468 total
includes taxes & fees
Oct 6 - Oct 7
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, (49 reviews)
"Great place for big families and small children. "
United States
Maria R.
The price is CA $250
CA $665 total
includes taxes & fees
Sep 18 - Sep 19
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
10.0 out of 10, Exceptional, (40 reviews)
"Great location. Property was well stocked, clean and comfortable."
United States
Joe T.
The price is CA $281
CA $600 total
includes taxes & fees
Sep 22 - Sep 23
Rustic Owl w/ 2Kings In Fleming Island
A modern kitchen with dark wood cabinets, a stainless steel refrigerator, and a built-in sink with a dish rack.

8. Duplex Unit w/ Movie Theater, Kayaks & EV Charger

Duplex Unit w/ Movie Theater, Kayaks & EV Charger
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 CA $124
CA $422 total
includes taxes & fees
Sep 20 - Sep 21
Duplex Unit w/ Movie Theater, Kayaks & EV Charger
A living room with a sofa, coffee table, TV, fireplace, and a dining area in the background.

9. 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 CA $250
CA $665 total
includes taxes & fees
Sep 18 - Sep 19
Sunset near the lake up to 12 guests,4bds,2baths
A modern living room with a large flat-screen TV displaying a cityscape. There is a sofa, a coffee table, and a small side table.

10. Historic Retreat: Projector & Pool Table

Historic 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 CA $130
CA $469 total
includes taxes & fees
Sep 20 - Sep 21
Historic Retreat: Projector & Pool Table
A dining area with a wooden table and chairs, a decorative heart sculpture, and a view of the outdoors.

11. 2Bedroom-Special @Graceful House

2Bedroom-Special @Graceful House
Westside
The price is CA $159
CA $470 total
includes taxes & fees
Sep 22 - Sep 23
2Bedroom-Special @Graceful House
A bathroom shelf with toiletries, a cotton set, and neatly folded towels.

12. 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, (46 reviews)
"Great place to stay"
United States
Summer I.
The price is CA $152
CA $224 total
includes taxes & fees
Sep 30 - Oct 1
Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
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, (94 reviews)
"Beautiful home"
United States
Barbara M.
The price is CA $277
CA $745 total
includes taxes & fees
Sep 22 - Sep 23
Gorgeous circa 1875 Plantation House (in city)
A screened porch with a bench and a chair, surrounded by large green leaves.

14. The Historic Van Zant House - Lynyrd Skynyrd 1500 sq ft King

The Historic Van Zant House - Lynyrd Skynyrd 1500 sq ft King
Westside
9.2 out of 10, Wonderful, (29 reviews)
"We had a lot of fun with some friends that go way back to high school. This place makes a good get away."
United States
Marty W.
The price is CA $146
CA $355 total
includes taxes & fees
Sep 20 - Sep 21
The Historic Van Zant House - Lynyrd Skynyrd 1500 sq ft King
A modern living room with a sofa, a dining area with a table and chairs, a kitchen with white cabinets, and a TV in the background.

15. 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 CA $462
CA $1,026 total
includes taxes & fees
Sep 22 - Sep 23
Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths
A kitchen with wooden flooring, white cabinets, a stove, and a ceiling fan.

16. Roomy Murray Hill Couples Retreat

Roomy Murray Hill Couples Retreat
Northwest
10.0 out of 10, Exceptional, (6 reviews)
"Super cute place! It is a charming old duplex that has been updated. I love that the owners kept what apperas to be some original features like the kitchen sink and the cabinets. "
United States
Susan J.
The price is CA $111
CA $313 total
includes taxes & fees
Sep 21 - Sep 22
Roomy Murray Hill Couples Retreat
A dining room with a wooden table, four chairs, two lamps, and two windows with a view of a house and flowers.

17. Cozy Home in Avondale - Walkable to Food & Shops!

Cozy Home in Avondale - Walkable to Food & Shops!
Westside
The price is CA $107
CA $431 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Home in Avondale - Walkable to Food & Shops!
A porch with a wooden chair, a white door with a wreath, and a window with a green view.

18. Charming 3-bedroom House with AC and WiFi in lovely Jacksonville

Charming 3-bedroom House with AC and WiFi in lovely Jacksonville
Northwest
8.6 out of 10, Excellent, (28 reviews)
"Clean home great host "
United States
Dejari B.
The price is CA $125
CA $285 total
includes taxes & fees
Sep 19 - Sep 20
Charming 3-bedroom House with AC and WiFi in lovely Jacksonville
A modern kitchen with stainless steel appliances, a built-in island, and a dining area with a sofa and chairs.

19. Modern Riverside Home • Sleeps 8 • Near Downtown

Modern Riverside Home • Sleeps 8 • Near Downtown
Northwest
9.8 out of 10, Exceptional, (29 reviews)
"House was very clean. Close to everything. A lot of space in the house Host was amazing. Would definitely stay again"
United States
Corey M.
The price is CA $145
CA $396 total
includes taxes & fees
Sep 30 - Oct 1
Modern Riverside Home • Sleeps 8 • Near Downtown
A modern kitchen with wooden flooring, a built-in oven, and a refrigerator.

20. 2-bedroom townhome in Bartram Park, full remote work set up.

2-bedroom townhome in Bartram Park, full remote work set up.
Jacksonville
8.4 out of 10, Very good, (6 reviews)
"Was a convenient stop for our stay in town."
United States
Jeni M.
The price is CA $152
CA $372 total
includes taxes & fees
Sep 27 - Sep 28
2-bedroom townhome in Bartram Park, full remote work set up.
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 and a newer hotel. It does not have the weed smell that so many hotels have now! It’s a convenient location. The staff were efficient and kind. This was my 3rd stay here and I would definitely stay again."
Thomas 6-night trip
Posted 1 hour ago
Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station
Midtown Lodge

Midtown Lodge

8/10 Good
"Room was fine. They really should put somewhere on the webpage that there is a $20 room deposit before you book the room online."
Gilbert 1-night trip
Posted 2 days ago
Midtown Lodge

Find out more about Middleburg

Middleburg Vacation Homes information

Number of reviews
562
Accommodation
651 Vacation Homes
Lowest Price
CA $224
Highest Price
CA $1,026

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