Search Villas in Upperville

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 7 Villas in Upperville with updated reviews, rates, and availability.

Private10000sf Retreat GuitarPool Hottub-Wine Area
Interior

Private10000sf Retreat GuitarPool Hottub-Wine Area

10.0 out of 10, Exceptional, (21)
"Thank you for making our stay so seamless. We were comfortable and able to have a lot of fun and get a lot accomplished. It’s a great area!"
Private10000sf Retreat GuitarPool Hottub-Wine Area
Stunning Former Winery w/ Pool & Mtn Views!
Exterior

Stunning Former Winery w/ Pool & Mtn Views!

9.4 out of 10, Exceptional, (9)
"This place was perfect for our family and wedding party to all stay together. There was plenty of room, everyone was comfortable, and the scenery was fabulous!"
Stunning Former Winery w/ Pool & Mtn Views!
Historic Virginia Wine Country Villa w/ Pool, Yard
Outdoor dining

Historic Virginia Wine Country Villa w/ Pool, Yard

7.6 out of 10, Good, (15)
"The rooms were very engaging. My daughter-in-law was charmed. We had lots of indoor places in which to play. The pool in the backyard was great for adults & children during the warm summer!"
Historic Virginia Wine Country Villa w/ Pool, Yard
Elegant Paris Manor w/ Private Pool!
Property grounds

Elegant Paris Manor w/ Private Pool!

10.0 out of 10, Exceptional, (1)
"Wonderful property with wonderful people. The Manor house is incredible. The pool and the outdoor space was exactly what we had hoped for. Everyone really enjoyed the wagon ride to the top of the property. Definitely would recommend this family or just a getaway for 2 on a weekend!! John"
Elegant Paris Manor w/ Private Pool!
Elegant Paris Manor w/ Private Pool!
Interior

Elegant Paris Manor w/ Private Pool!

3.0 star property
Elegant Paris Manor w/ Private Pool!
Stunning Former Winery w/ Pool & Mtn Views!
Exterior

Stunning Former Winery w/ Pool & Mtn Views!

3.0 star property
Stunning Former Winery w/ Pool & Mtn Views!
Historic Virginia Wine Country Villa w/ Pool, Yard
Outdoor dining

Historic Virginia Wine Country Villa w/ Pool, Yard

3.0 star property
Historic Virginia Wine Country Villa w/ Pool, Yard
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 Upperville
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Upperville

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Smart TV, DVD player, books, video library

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

10.0 out of 10, Exceptional, (59)
"Beautiful views. Cozy, exceptionally clean and wonderful house. Highly reccomend!"
The price is AED 569
AED 1,247 total
includes taxes & fees
31 Mar - 1 Apr
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"Loved it "
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Hot Tub, Game Room, River Access, Fire Pit & Grill
Interior

Hot Tub, Game Room, River Access, Fire Pit & Grill

9.6 out of 10, Exceptional, (22)
"This was a perfect place for our group. Bedroom for everyone, up and down tvs for movie and sports watching, table for gaming, and hrs in the hot tub. Dining table was big enough for everyone to eat together, and the kitchen had what we needed to manage all our meals"
The price is AED 783
AED 1,397 total
includes taxes & fees
31 Mar - 1 Apr
Hot Tub, Game Room, River Access, Fire Pit & Grill
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

Why book your villa in Upperville with Expedia?
We think organizing a vacation should be hassle-free, so if you’re on the lookout for villas at a competitive rate, Expedia can help. Keep costs down and go for an all-inclusive stay, or splurge on a luxe villa to spoil your favorite people. Our handy filters make it simple to find a retreat in Upperville that matches your needs.
How can I find cheap villas in Upperville?
The easiest way to locate cheap villas in Upperville is with Expedia’s helpful filter tool. Narrow your search by amenities, star rating and budget to land unbeatable bargains in just a couple of clicks.