Photo by Stephanie Sutton

Middleburg Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Middleburg

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (33)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is AU$640
includes taxes & fees
15 Jan - 16 Jan 2025
18th Century Stone Cottage minutes from historic Middleburg

Global Luxury Suites at Reston Town Center

3.5 star property
8.2 out of 10, Very good, (121)
"The location, the building and the property manager, Bushra, were excellent. Lots of local businesses are walkable and a great Reston Town Center location. "
The price is AU$463
includes taxes & fees
2 Jan - 3 Jan 2025
Global Luxury Suites at Reston Town Center

Breathtaking views with an indoor private pool, come escape with us

9.8 out of 10, Exceptional, (242)
"We thoroughly enjoyed the cozy lodge vibe and the different spaces it offered our group. The host, Leslie, was always available for any questions we had. She also had the place decorated for Christmas which warmed our hearts!! Thank you Bear Chase for a great weekend. "
Breathtaking views with an indoor private pool, come escape with us

Global Luxury Suites at Reston

4.0 star property
7.6 out of 10, Good, (7)
"Water pressure was terrible in the kitchen and shower. Furniture broken. Coffee but No filters for coffee maker. Too expensive for 2-3 hours late check out. "
The price is AU$439
includes taxes & fees
29 Dec - 30 Dec
Global Luxury Suites at Reston

Rustic Log Cabin with Private Dock on the Lake!

9.6 out of 10, Exceptional, (12)
"Amazing location!!! 18 minutes from a cluster of wineries; quiet and relaxing. Definitely will be visiting again "
The price is AU$661
includes taxes & fees
5 Jan - 6 Jan 2025
Rustic Log Cabin with Private Dock on the Lake!

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

10.0 out of 10, Exceptional, (52)
"It was so nice. We were bummed to only be there one night. Such a lovely set up. Would definitely recommend to anyone. Although I have to say the trip up the hill was similar to a roller coaster ride, such fun."
The price is AU$482
includes taxes & fees
21 Jan - 22 Jan 2025
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

Escape to Shenandoah River, Hot Tub after a Hike!

10.0 out of 10, Exceptional, (41)
"Myself and 5 other friends stayed here for a weekend and it was perfect! The house was awesome and had everything we needed. There was plenty of space, a lovely hot tub, a firepit, and beautiful scenery. The inside felt very welcoming and the check-in/check-out process was extremely easy. We loved this stay!"
The price is AU$601
includes taxes & fees
13 Jan - 14 Jan 2025
Escape to Shenandoah River, Hot Tub after a Hike!

Insta Worthy Mountain Views and Hot Tub

10.0 out of 10, Exceptional, (8)
"This mountain house is absolute beauty! It is beyond gorgeous. The view is spectacular, the sunset is breathtaking. You have a 180 degrees view of West VA. The house itself is stunning, plenty of rooms to move around with our group of 15. We enjoyed the jacuzzi while admiring the beautiful sunset. The kids had fun roasting marshmallows while Eagles are flying up above them. Thank you for sharing this Eagle’s Nest home. 😊"
The price is AU$1,689
includes taxes & fees
27 Jan - 28 Jan 2025
Insta Worthy Mountain Views and Hot Tub

Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

9.8 out of 10, Exceptional, (20)
"My friends and I always choose a new cabin for our annual fall getaway. We've not had a bad experience yet. Mountain Mama's Woodpecker Woods did not disappoint, either! Comfortable, warm, clean, spacious log cabin. It had everything we needed. In fact, it was so relaxing, we never made it to the hot tub. We did visit Harper's Ferry Park and enjoyed walking the hiking trail to the downtown area. :-) We especially loved the close proximity to the Washington, DC Metro area. If there was anything...
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

10.0 out of 10, Exceptional, (79)
"My husband and I had a lovely stay in this cabin for Thanksgiving. We had everything we needed to cook our Thanksgiving meal, stay cozy, and enjoy the views around the cabin. Thank you!"
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
Terra Alta - Incredible River Views and Hot Tub!

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

9.8 out of 10, Exceptional, (25)
"Hiking, playing in the creek, S'mores by the fire pit, enjoying meals on the porch all add up to fun memories. We enjoyed our stay. "
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Charming Home with Yard Near Shenandoah River!

9.8 out of 10, Exceptional, (15)
"All was very, very good. "
Charming Home with Yard Near Shenandoah River!

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (92)
"Wonderful Thanksgiving in a wonderful home with our family."
Gruner Bungalow at Otium Cellars

Beautiful 1BR Walkout Fenced & Gated Villa, Onsite parking, Pet friendly-2+acres

9.2 out of 10, Wonderful, (13)
"Great space for me to sleep and relax for a couple days!"
Beautiful 1BR Walkout Fenced & Gated Villa, Onsite parking, Pet friendly-2+acres

Cozy Cabin Hidden Away on a Lake!

9.6 out of 10, Exceptional, (37)
"The cabin was nice . Great view. Mostly clean , but the coffee pot was very dirty. There was plenty of coffee, but no filters.The grill was very dirty and the grill bush was in such bad condition it was un-usable."
The price is AU$1,529
includes taxes & fees
29 Dec - 30 Dec
Cozy Cabin Hidden Away on a Lake!

13 BR Boutique in Berryville

7.4 out of 10, Good, (6)
"This house is a gem in progress. It was very spacious and naturally divided into separate areas so it worked well to group families with small children away from older couples without children. Several issues did develop during our stay which were immediately addressed. The dish washer was repaired and worked fine for us. The large common area had very minimal lighting but we moved lamps into the area to remedy that. There was ample refrigerator space but no freezer so we improvised with ice...
13 BR Boutique in Berryville

Bear Chase Cottage

10.0 out of 10, Exceptional, (32)
"The cabin was perfect! Clean and cozy. We wish we could have extended our stay! We will definitely come back! "
Bear Chase Cottage

Cozy home near Casino, Breweries, Historical attractions, National Park & more

10.0 out of 10, Exceptional, (20)
"VERY NICE PLACE"
The price is AU$478
includes taxes & fees
6 Jan - 7 Jan 2025
Cozy home near Casino, Breweries, Historical attractions, National Park & more

Beautiful 2BR Walkout Fenced & Gated Villa, Onsite parking, Pet friendly-2+acres

8.6 out of 10, Excellent, (15)
"We loved Maryland and my son says it’s one of the most beautiful places he’s been. Less than 15 minutes from a charming little town called Potomac with shopping and good food. The property is lovely and the rooms were great. We used the kitchen and watched movies to wind down. Our trip into DC was smooth and the scenery was beautiful. We plan to return in July 2026 and bring the rest of the family. "
Beautiful 2BR Walkout Fenced & Gated Villa, Onsite parking, Pet friendly-2+acres
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.
Don't see what you're looking for?
See all available properties in Middleburg
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Middleburg you may be interested in

Salamander Resort And Spa

5.0 star property
9.2 out of 10, Wonderful, (331)
"Loved our stay. Would have liked to receive the VIP gift we should have. "
The price is AU$1,147
includes taxes & fees
12 Jan - 13 Jan 2025
Salamander Resort And Spa

The Red Fox Inn & Tavern

4.0 star property
9.6 out of 10, Exceptional, (327)
"Revisiting my past after 25 yrs. Feels like home "
The price is AU$595
includes taxes & fees
2 Jan - 3 Jan 2025
The Red Fox Inn & Tavern

Hyatt Regency Dulles

4.0 star property
8.8 out of 10, Excellent, (1208)
"Adequate for the need at the time"
The price is AU$202
includes taxes & fees
11 Jan - 12 Jan 2025
Hyatt Regency Dulles
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.

Frequently asked questions

Can I find holiday rentals in Middleburg?

Yes, there are holiday rentals in Middleburg close to National Sporting Library & Museum, or you can select a more secluded option if you're looking for a relaxing stay. The spas and restaurants are several reasons why visitors like Middleburg. Make sure you have time to check out the wineries while you're in the area.

What are some of the best holiday rentals that Middleburg has to offer?

Breathtaking views with an indoor private pool, come escape with us: This holiday home rental outside of Middleburg is located in the mountains, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Middleburg?

Expedia has 12 holiday rentals for your stay in Middleburg.

What’s there to see and do in Middleburg?

Cultural attractions include Red Fox Fine Art and The Byrne Gallery, whereas National Sporting Library & Museum is just one of the family-friendly sights. Other places in town to visit include Greenhill Winery & Vineyards and Cana Vineyards and Winery.

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 offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.