Best Vacation Homes in Middleburg
House
10.0(71 Reviews)
3 Bedrooms
2 Baths
6 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
£313/Night
7 Nights - £2,189
House
10.0(1 Review)
4 Bedrooms
3 Baths
9 Guests
2421.88 ft²
Hot Tub- Fireplace/Heating
- Pet Friendly
Parking
£475/Night
7 Nights - £3,328
House
8.0(16 Reviews)
1 Bedroom
1 Bath
- Hot Tub
Pool- Balcony/Terrace
Breakfast
£267/Night
7 Nights - £1,872
Cottage
10.0(52 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£293/Night
7 Nights - £2,051
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
2195.84 ft²
Spa- Fireplace/Heating
- Parking
Internet
£373/Night
7 Nights - £2,609
Cottage
10.0(46 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£259/Night
7 Nights - £1,816
House
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£127/Night
7 Nights - £889
House
2 Bedrooms
1 Bath
4 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£202/Night
7 Nights - £1,417
Middleburg Luxury Rentals
House
3 Bedrooms
4 Baths
10 Guests
4018 ft²
- Fireplace/Heating
Air Conditioner- Internet
Child Friendly
£2,987/Night
7 Nights - £20,908
House
10.0(41 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£1,545/Night
7 Nights - £10,815
House
10.0(15 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£1,542/Night
7 Nights - £10,794
House
10.0(4 Reviews)
7 Bedrooms
7 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
£1,527/Night
7 Nights - £10,688
House
10.0(2 Reviews)
9 Bedrooms
6 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
£1,337/Night
7 Nights - £9,357
House
10.0(15 Reviews)
5 Bedrooms
5 Baths
10 Guests
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
£1,179/Night
7 Nights - £8,250
House
6 Bedrooms
6 Baths
16 Guests
4220 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£920/Night
7 Nights - £6,437
Resort
8.9(39 Reviews)
1 Bath
33 Guests
696.07 ft²
- Private Pool
Oceanfront- Hot Tub
- Spa
£674/Night
7 Nights - £4,717
Middleburg Pet Friendly Vacation Rentals
House
10.0(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£651/Night
7 Nights - £4,554
House
3 Bedrooms
2 Baths
5 Guests
2195.84 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
£291/Night
7 Nights - £2,035
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
5 Guests
2200 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£360/Night
7 Nights - £2,517
Hotel
9.2(38 Reviews)
13 Baths
985.31 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
£242/Night
7 Nights - £1,693
Cottage
9.8(161 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£176/Night
7 Nights - £1,232
Cottage
9.8(86 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£134/Night
7 Nights - £939
Apartment
9.8(25 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£203/Night
7 Nights - £1,419
House
9.6(13 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£173/Night
7 Nights - £1,210
Middleburg Large Vacation Homes
Other
10.0(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£488/Night
7 Nights - £3,414
Villa
9.2(57 Reviews)
2 Bedrooms
3 Baths
5 Guests
1038.72 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
Ocean View
£242/Night
7 Nights - £1,693
House
9 Bedrooms
6 Baths
16 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
£1,260/Night
7 Nights - £8,817
House
10.0(7 Reviews)
4 Bedrooms
3 Baths
12 Guests
2800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£492/Night
7 Nights - £3,447
House
10.0(5 Reviews)
4 Bedrooms
5 Baths
10 Guests
5000 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
£814/Night
7 Nights - £5,700
Villa
10.0(2 Reviews)
4 Bedrooms
8 Baths
8 Guests
3850 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
£1,692/Night
7 Nights - £11,842
House
3 Bedrooms
3 Baths
17 Guests
10000 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
£1,166/Night
7 Nights - £8,164
House
4 Bedrooms
4 Baths
12 Guests
6500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
£803/Night
7 Nights - £5,623
Why Choose Rent By Owner for your Middleburg Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Middleburg
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can greatly enhance your experience, as this destination offers different charms and activities depending on the season, making it essential to plan your trip when the region's natural beauty and local events align with your interests.
Peak Season Highlights
Spring (March to May)
During this period, the region experiences its most vibrant and inviting climate, making it an ideal time to explore scenic landscapes and enjoy outdoor activities. The pleasant temperatures attract visitors seeking a memorable stay in charming vacation rentals.
Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
Fall (September to November)
Autumn is a popular time to visit here, thanks to the stunning fall foliage and mild weather. This season draws travelers looking for a cozy getaway in well-appointed vacation rentals amidst picturesque scenery.
Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F
Off-Season Highlights
Winter (December to February)
The winter months see fewer visitors, offering a quieter atmosphere and a chance to enjoy peaceful stays in comfortable vacation rentals. Cooler temperatures create a perfect setting for relaxing indoors or exploring nearby indoor activities.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Early Spring & Late Fall (March and late November)
During these shoulder seasons, the area tends to be less crowded, providing a more tranquil experience. Moderate temperatures make it a suitable time for those seeking quieter rentals and a leisurely exploration of the countryside.
Average Temperature Daytime: 50-60°F - Nighttime: 30-40°F
Weekly Weather Forecast for Middleburg
How to Book Your Middleburg Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Middleburg
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy relaxing evenings around a private outdoor fire pit, perfect for unwinding after exploring the region’s scenic countryside.
- Take advantage of spacious patios or decks to dine al fresco while soaking in the picturesque views of this charming area.
- Benefit from well-maintained gardens and landscaped yards that offer a tranquil setting for outdoor activities.
- Make use of a refreshing swimming pool to cool off during warm summer days in this inviting destination.
- Utilize outdoor grilling stations or barbecue areas to host memorable cookouts with friends and family.
- Explore expansive lawns or open spaces ideal for outdoor games and recreational activities in the region.
- Discover shaded pergolas or gazebo structures that provide a cozy spot to relax outdoors and enjoy the fresh air.
Top Attractions Around Middleburg
What attractions are nearby?
In this charming destination, you can explore scenic wine tours, visit historic sites, or enjoy outdoor activities like horseback riding and hiking within the picturesque region surrounding your rental.
Family Activities
- Visit the National Sporting Library & Museum: Engage with this regional treasure that offers interactive exhibits and programs, perfect for family learning experiences in the area.
- Explore the Middleburg Community Center: Participate in family-friendly events and activities designed to bring visitors together while showcasing local culture and community spirit.
- Enjoy outdoor adventures at the nearby parks: Discover open green spaces and scenic trails ideal for picnics, nature walks, and active play suited for all ages here.
- Discover local wineries with family-friendly tours: Experience charming vineyard visits where some estates offer engaging activities for children, giving you a taste of the region’s rich viticulture heritage.
Adult Activities
- Wine Tasting Tours: Experience the region’s renowned wineries with guided tastings that showcase some of Virginia's finest vineyards.
- Horseback Riding: Explore scenic trails on horseback, immersing yourself in the area's equestrian heritage and picturesque landscapes.
- Art Galleries and Studios: Discover local artistry by visiting galleries and studios that highlight the region’s vibrant creative community.
Other Places to Stay in Middleburg, VA
Cana Vineyards and Winery
Chrysalis Vineyards
Tudor Day Spa
Glenwood Park
Trowbridge-Lewis Galleries
Red Fox Fine Art
The Byrne Gallery
The Sporting Gallery
Piedmont Vineyards and Winery
National Sporting Library & Museum
Greenhill Winery & Vineyards
Middleburg Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Wineries and Vineyards: Take advantage of the region's renowned wine culture by visiting nearby wineries to enjoy tastings and learn about local viticulture.
- Plan Outdoor Activities: Make the most of the area's scenic landscapes with outdoor pursuits such as horseback riding, hiking, or cycling along picturesque trails.
- Visit Charming Town Centers: Spend time exploring quaint downtown areas filled with boutiques, art galleries, and cozy cafes that showcase the region’s unique character.
- Experience Seasonal Events: Check the local event calendar for seasonal festivals and markets that highlight the area's rich traditions and community spirit.
Transportation Options
- Car Rentals: Easily explore the area and nearby attractions with rental cars available at key locations around Middleburg, Virginia.
- Taxi Services: Reliable taxi services operate throughout the region, providing convenient transportation options during your stay.
- Public Transit: Local bus services connect you to the broader region, making it simple to navigate without a private vehicle.
- Rideshare Options: Ridesharing platforms are readily accessible in this destination, offering a flexible way to get around comfortably during your visit.
Local Customs Options
- Horse Country Hospitality: Locals take pride in their equestrian heritage, often incorporating horse-related traditions and events into community life here.
You’ll find that regional dishes and locally sourced ingredients are celebrated, reflecting the region’s rich agricultural roots.
Frequently Asked Questions About Middleburg?
1. What are the top vacation rentals in Middleburg?
There are a lot of options in Middleburg. If you plan on staying in the Middleburg area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middleburg:
- CEDAR LANE - Private Cottage, Sophisticated Country Charm
- Hunt Box-Antique Filled Cottage on Lowelands Farm-MiddleburgnZONR-2024-012704
- YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
- 'Anny's Farm House' Near Middleburg & Wineries!
- Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
- Country Cottage on 1700’s Horse Farm/Wedding Venue
- 18th Century Stone Cottage minutes from historic Middleburg
- Lovely Guest House 2.5 miles from downtown Middleburg
- Elegant Middleburg Manor with 3 Bedrooms 2 Baths
- Spacious Modern Home on Middleburg Horse Farm
2. Which vacation homes in Middleburg are best for families?
If you are looking for a family-friendly vacation home in Middleburg, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middleburg:
3. How many Rentbyowner vacation rentals are available in Middleburg?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 73 in the Middleburg area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Middleburg.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so it's important to review the specific listing details or contact the owner directly to understand the terms and any applicable fees.
5. How do I find the best vacation rental deals in Middleburg, Virginia?
You can compare listings based on price, amenities, and reviews, and reach out to property owners for any special offers or discounts available during your travel dates.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or security deposits are typically outlined in the listing. Always read the full property description or ask the owner for clarification.
7. Can I get assistance with my booking or questions after I reserve a vacation rental?
Yes, most hosts and property managers offer support before and during your stay. You can contact them directly through the booking platform for any inquiries or assistance.
8. What amenities should I look for when booking a vacation rental in the region?
Popular amenities include complimentary Wi-Fi, parking, outdoor spaces, and modern appliances. Be sure to check each listing for the features that will make your stay comfortable.
Middleburg Top Rated Vacation Rentals
Other
10.0(64 Reviews)
3 Bedrooms
3 Baths
9 Guests
2800 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
£237/Night
7 Nights - £1,658
Bed & Breakfast
9.8(37 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£354/Night
7 Nights - £2,476
Hotel
9.6(50 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
£465/Night
7 Nights - £3,252
£515/Night
7 Nights - £3,606
Bed & Breakfast
9.0(69 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£307/Night
7 Nights - £2,150
Bed & Breakfast
8.8(21 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
£184/Night
7 Nights - £1,287
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
5 Guests
2200 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£261/Night
7 Nights - £1,827
Apartment
3 Bedrooms
1 Bath
2 Guests
550 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Air Conditioner
£661/Night
7 Nights - £4,625
