House
10.0(76 Reviews)
2 Bedrooms
6 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $466/Night
7 Nights - US $3,264
Upperville Holiday Rentals
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Compare Villas, Resorts, & Rentals in Upperville
10.0
House
10.0(1 Review)
3 Bedrooms
7 Guests
Oceanfront- Parking
Ocean View
View
US $401/Night
7 Nights - US $2,805
House
9 Bedrooms
16 Guests
- Air Conditioner
Internet
Laundry
Bedding/Linens
US $1,693/Night
7 Nights - US $11,850
Cottage
10.0(65 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $396/Night
7 Nights - US $2,772
US $1,910/Night
7 Nights - US $13,370
Cottage
10.0(52 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $427/Night
7 Nights - US $2,989
Cottage
10.0(37 Reviews)
2 Bedrooms
3 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $273/Night
7 Nights - US $1,912
House
10.0(25 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $347/Night
7 Nights - US $2,426
Cottage
9.8(54 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $263/Night
7 Nights - US $1,840
Luxury Holiday Rentals in Upperville
Over 46+ Luxury Holiday Rentals in or Near Upperville
Villa
10.0(2 Reviews)
6 Bedrooms
13 Guests
Private Pool- Parking
Pool- Balcony/Terrace
US $2,372/Night
7 Nights - US $16,603
New
House
10.0(2 Reviews)
9 Bedrooms
16 Guests
- Air Conditioner
- Internet
Pet Friendly
Child Friendly
US $2,334/Night
7 Nights - US $16,335
House
10.0(4 Reviews)
7 Bedrooms
14 Guests
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $2,314/Night
7 Nights - US $16,199
House
10.0(1 Review)
6 Bedrooms
16 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,184/Night
7 Nights - US $8,287
House
10.0(2 Reviews)
7 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,123/Night
7 Nights - US $7,860
House
10.0(16 Reviews)
5 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,107/Night
7 Nights - US $7,751
House
10.0(36 Reviews)
5 Bedrooms
11 Guests
- Air Conditioner
- Laundry
- Bedding/Linens
Wellness Facilities
US $1,053/Night
7 Nights - US $7,368
House
10.0(6 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $935/Night
7 Nights - US $6,542
House
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $797/Night
7 Nights - US $5,581
Top-Rated Holiday Rentals with a Pool in Upperville
Over 3+ The Best Private Villas and Holiday Rentals in Upperville with a Pool
House
10.0(2 Reviews)
7 Bedrooms
18 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $1,643/Night
7 Nights - US $11,502
Cabin
9.8(58 Reviews)
7 Bedrooms
14 Guests
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $794/Night
7 Nights - US $5,559
Cabin
3 Bedrooms
4 Guests
Hot Tub- Parking
- Pool
- Balcony/Terrace
US $380/Night
7 Nights - US $2,659
Pet-Friendly Holiday Rentals in Upperville
Over 16+ Pet-Friendly Holiday Rentals in or Near Upperville
House
8.8(9 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $254/Night
7 Nights - US $1,780
House
5 Bedrooms
12 Guests
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $526/Night
7 Nights - US $3,679
Cottage
10.0(15 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $502/Night
7 Nights - US $3,511
House
1 Bedroom
8 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $436/Night
7 Nights - US $3,055
House
10.0(13 Reviews)
4 Bedrooms
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $402/Night
7 Nights - US $2,817
House
10.0(7 Reviews)
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $423/Night
7 Nights - US $2,963
House
10.0(5 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $464/Night
7 Nights - US $3,245
House
9.8(71 Reviews)
5 Bedrooms
14 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $579/Night
7 Nights - US $4,056
Cabin
9.6(8 Reviews)
3 Bedrooms
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $527/Night
7 Nights - US $3,692
Large Holiday Rentals and Private Villas in Upperville
Over 6+ Large Holiday Rentals and Private Villas in or Near Upperville
House
8.6(7 Reviews)
5 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $536/Night
7 Nights - US $3,754
House
1 Bedroom
12 Guests
- View
- Air Conditioner
- Internet
- Child Friendly
US $462/Night
7 Nights - US $3,237
House
7.6(5 Reviews)
7 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $831/Night
7 Nights - US $5,814
House
9.4(13 Reviews)
5 Bedrooms
10 Guests
- Breakfast
- Pet Friendly
- Child Friendly
- Bedding/Linens
US $606/Night
7 Nights - US $4,239
House
8.0(4 Reviews)
4 Bedrooms
11 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $732/Night
7 Nights - US $5,121
House
5.0(1 Review)
7 Bedrooms
12 Guests
- Kitchen
- Air Conditioner
TV- Bedding/Linens
US $316/Night
7 Nights - US $2,212
Upperville Private Villas and Holiday Homes Under $200
Over 3+ Upperville Private Villas and Holiday Homes Under $200
House
10.0(6 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $181/Night
7 Nights - US $1,267
Cabin
10.0(2 Reviews)
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $182/Night
7 Nights - US $1,274
US $150/Night
7 Nights - US $1,050
Instantly Bookable Holiday Homes in Upperville
Over 11+ Instantly Bookable Holiday Homes in or Near Upperville
House
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $306/Night
7 Nights - US $2,140
US $281/Night
7 Nights - US $1,968
Cabin
10.0(22 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $556/Night
7 Nights - US $3,891
House
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $364/Night
7 Nights - US $2,550
Apartment
9.4(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $224/Night
7 Nights - US $1,569
Cabin
10.0(80 Reviews)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $249/Night
7 Nights - US $1,746
House
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $1,386/Night
7 Nights - US $9,702
House
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $243/Night
7 Nights - US $1,699
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $349/Night
7 Nights - US $2,441
Book a Last Minute Place to Stay in Upperville
About Casai's Private Villas and Holiday Rentals in Upperville
Discover more than 55 vacation rentals available in Upperville. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Upperville.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Upperville, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Upperville. On average, places to stay near Upperville offer 1272.65 ft², with nightly prices averaging US $671.
With Casai, finding and comparing holiday rentals in Upperville is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
There are 55 Upperville, VA Holiday Rentals
- Prices for a holiday home in Upperville start at US $254
- Top rated vacation home in Upperville is Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
- Most popular short term in Upperville is Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
- Cheapest place to stay in Upperville is Historic Farmhouse Suite in Virginia Hunt & Wine Country
- Most expensive holiday rental in Upperville is Elegant Paris Manor w/Private Pool!
Recently Booked Holiday Rentals in Upperville
Frequently Asked Questions About Upperville?
What are the top holiday rentals in Upperville?
With numerous options available in Upperville, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Upperville:
- Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
- 18th Century Stone Cottage minutes from historic Middleburg
- Lovely Guest House 2.5 miles from downtown Middleburg
- Hunt Country cottage in Upperville!
- Historic house in Upperville! Wineries, equestrian events, great location!
- Cozy Country Getaway in the Heart of Upperville
- Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
- Renovated 1880s farmhouse near the Blue Ridge and Sky Meadows with amazing views
- Charming 3-bedroom cottage located on historic Seaton Place Farm in Delaplane VA
- Historic home nestled in the heart of horse and wine country. Kids/pet friendly!
Which holiday homes in Upperville are best for families?
If you're searching for a family-friendly holiday home in Upperville, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Upperville:
How many Casai.com holiday rentals are available in Upperville?
As of 2026, Casai boasts over 55 properties listed in the Upperville area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Upperville.
