Photo by Stephanie Sutton

Holiday Rentals in Middleburg

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Holiday Rentals in Middleburg

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (36)
"Adorable cottage. Well appointef"
The price is €382
includes taxes & fees
17 Feb - 18 Feb
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, (123)
"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 €254
includes taxes & fees
20 Feb - 21 Feb
Global Luxury Suites at Reston Town Center

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

9.8 out of 10, Exceptional, (244)
"Our group had an amazing stay at the Bear Chase Manor! The house has great common space areas and the pool was a huge hit with everyone. We also loved the convenience of being next to the brewery along with the incredible views of nature. Can't wait to have the opportunity to stay here again!"
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, (11)
"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 €238
includes taxes & fees
17 Feb - 18 Feb
Global Luxury Suites at Reston

Cozy Mountain Cabin w/ Steam Shower. Great for Couples!

10.0 out of 10, Exceptional, (54)
"The cabin was very nice and quaint. We had a nice stay. The view from the sunroom is great amazing. The place is very cozy and made for a great night away. "
The price is €294
includes taxes & fees
24 Feb - 25 Feb
Cozy Mountain Cabin w/ Steam Shower. Great for Couples!

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, (53)
"This was an amazing place to stay. Not too far of a drive from many different activities and a beautiful home. Be warned it is up on a hill so winter stays are more precarious - we ended up leaving a day early out of an abundance of caution due to a large winter storm system moving in. "
The price is €396
includes taxes & fees
20 Feb - 21 Feb
Terra Alta - Incredible River Views and Hot Tub!

Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

9.8 out of 10, Exceptional, (20)
"My wife and I spent a long weekend here with another couple. There are a few other houses nearby, but we really didn't see anyone other than when they were coming or going, but we did see a few deer. It was nice just sitting out by the firepit with glasses of wine and just relaxing, and hearing none of the normal city or suburb noises. There was plenty of space in the cabin itself, and everything we needed was there. It was a great place to unwind."
The price is €347
includes taxes & fees
17 Feb - 18 Feb
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

Global Luxury Suites at Town Center

4.0 star property
4.0 out of 10, (1)
"The property was undeniably beautiful and spacious, but the pre-arrival process was a disaster. I booked a Global Luxury Suites hotel via hotels.com, only to find it was actually the Skymark building, owned by Churchill. I opted to pay upon arrival, yet my card was charged in full 7-10 days before my stay without any explanation. Attempts to resolve this with hotels.com failed; they couldn't contact the company. A search for "Global Luxury Suites, Reston VA" revealed it didn't exist. I received...
The price is €257
includes taxes & fees
20 Feb - 21 Feb
Global Luxury Suites at Town Center

Tranquil Sugarland Retreat Close to Airport/Metro

10.0 out of 10, Exceptional, (15)
"It was the perfect place to crash for the night and wake up and enjoy nature before heading back home "
The price is €155
includes taxes & fees
19 Feb - 20 Feb
Tranquil Sugarland Retreat Close to Airport/Metro

Buckskin Manor - Historic, Pool, 66 Acre Vineyard

9.6 out of 10, Exceptional, (17)
"We had a fantastic stay at the property. The home is very charming and the pool is great. The location was also really nice. Close to wineries and hiking. Two points of feedback are that the dishes were visibly dirty upon arrival and all of the mattresses need to be replaced. Everyone in the group slept poorly and noted that the mattresses were uncomfortable. The master bedroom should likely also have a larger bed."
Buckskin Manor - Historic, Pool, 66 Acre Vineyard

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (93)
"It's was great. We visited family in the area. And had our family Christmas together at this place. We played ping pong and pool when we where there. Great location for dogs. Plenty of space to run and play. The house was great as well. Plenty of space for everyone."
Gruner Bungalow at Otium Cellars

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

10.0 out of 10, Exceptional, (54)
"The property is quite lovely, surrounded by the rolling hills of western Virginia. The house was perfect, a lot of space to spread out if needed. We spent our evenings on the screened in back porch. The pool and gardens were an added bonus. Every evening the neighbor cows would graze along the fence line- just a lovely get away from the City! "
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

10.0 out of 10, Exceptional, (9)
"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "
The price is €350
includes taxes & fees
25 Feb - 26 Feb
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

Cute cabin retreat near Shenandoah National Park and pet friendly!

9.2 out of 10, Wonderful, (10)
"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"
The price is €322
includes taxes & fees
16 Mar - 17 Mar
Cute cabin retreat near Shenandoah National Park and pet friendly!

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (43)
"We had an excellent stay at Jill’s VRBO! The home was spacious and clean, perfect for a relaxing weekend away. The location also is ideal for going to wineries near Leesburg and Middleburg. And Jill was a very attentive host— she made sure that someone was there to remove the snow from the driveway and responded to any messages we sent promptly."
Trailside Retreat in breathtaking Western Loudoun

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (41)
"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."
Charles Town Home w/ Private Pool & Hot Tub

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (31)
"This was a perfect long weekend stay for two families (4 adults, 4 kids). Comfortable, spacious, and well-equipped house on a beautiful property. Very responsive and helpful host. Would give 6 stars if I could. We hope to be back soon!"
Modern Country House on the Shenandoah River

Aslan's How - Cabin with Valley Views & Hot Tub!

2.0 star property
10.0 out of 10, Exceptional, (4)
"What a great stay. "
The price is €372
includes taxes & fees
17 Feb - 18 Feb
Aslan's How - Cabin with Valley Views & Hot Tub!

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
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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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, (338)
"Salamander is living up to its reputation for being elegant and upscale. But it's the staff, the food, and the overall excellent working conditions of everything that make this a wonderful place to stay."
The price is €647
includes taxes & fees
17 Feb - 18 Feb
Salamander Resort And Spa

The Red Fox Inn & Tavern

4.0 star property
9.6 out of 10, Exceptional, (340)
"Beautiful inn great food friendly staff, would recommend 👌 "
The price is €295
includes taxes & fees
17 Feb - 18 Feb
The Red Fox Inn & Tavern

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (36)
"Adorable cottage. Well appointef"
The price is €382
includes taxes & fees
17 Feb - 18 Feb
18th Century Stone Cottage minutes from historic Middleburg
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?

Charles Town Home w/ Private Pool & Hot Tub: This holiday home rental outside of Middleburg offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals will I find in Middleburg?

Expedia has 11 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.