Search Upperville Villa Rentals from CA $99

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months
No exact matches found, but these alternatives could be just right

Recommended hotels in Upperville

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,015 reviews)
"Great location, clean rooms and friendly staff."
United States
Daniel
The price is CA $105
CA $119 total
includes taxes & fees
May 31 - Jun 1
Spark by Hilton Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,099 reviews)
"Very friendly front desk Quiet surroundings. Great restaurant nearby"
United States
Rosemary
The price is CA $142
CA $154 total
includes taxes & fees
Jun 9 - Jun 10
Comfort Inn & Suites Winchester

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,009 reviews)
"Location is right across the road from Spelunker's, the best casual restaurant in Virginia."
United States
Rachel
The price is CA $95
CA $106 total
includes taxes & fees
May 18 - May 19
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1,012 reviews)
"I enjoyed my stay. The room was clean and the breakfast was varied."
United States
Brenda
The price is CA $160
CA $178 total
includes taxes & fees
May 25 - May 26
Hampton Inn Front Royal

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (88 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
The price is CA $230
CA $501 total
includes taxes & fees
May 18 - May 19
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1,012 reviews)
"Very friendly staff....new owners Restaurant has great food"
United States
Brian
The price is CA $142
CA $159 total
includes taxes & fees
May 24 - May 25
Clarion Inn Harpers Ferry - Charles Town

HomeTowne Studios by Red Roof Leesburg

HomeTowne Studios by Red Roof Leesburg
2.5 star property
Leesburg
The price is CA $160
CA $183 total
includes taxes & fees
Jun 14 - Jun 15
HomeTowne Studios by Red Roof Leesburg

Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (297 reviews)
"Wonderful stay at a beautiful spot."
United States
michael
The price is CA $190
CA $216 total
includes taxes & fees
May 18 - May 19
Loudoun Valley Manor

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,005 reviews)
"Breakfast was great and we love that they let us bring small dogs"
United States
Claire VanWinkle
The price is CA $121
CA $132 total
includes taxes & fees
May 25 - May 26
Quality Inn Winchester

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (34 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Host was responsive and helpful. Would definitely stay again."
United States
Wafaa L.
The price is CA $261
CA $326 total
includes taxes & fees
May 18 - May 19
Blue Mountain Cabin, secluded, perfect for couples, near main road

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,003 reviews)
"Staff are so nice and everything was good"
United States
Osama
The price is CA $129
CA $140 total
includes taxes & fees
Jun 7 - Jun 8
Country Inn & Suites by Radisson, Winchester, VA

Secluded cabin w/hot tub & deck, dog-friendly

Secluded cabin w/hot tub & deck, dog-friendly
Harpers Ferry
9.2 out of 10, Wonderful, (33 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is CA $268
CA $464 total
includes taxes & fees
May 21 - May 22
Secluded cabin w/hot tub & deck, dog-friendly

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (889 reviews)
"Location was excellent"
United States
Jennie
The price is CA $148
CA $167 total
includes taxes & fees
May 24 - May 25
Hampton Inn Winchester N/Conference Center, VA

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,005 reviews)
"The staff was helpful and kind. The architecture was incredible."
United States
Allison
The price is CA $168
CA $190 total
includes taxes & fees
May 25 - May 26
The George Washington Hotel, A Wyndham Grand Hotel

Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (29 reviews)
"Great place. Very clean, lots of comfortable rooms. Nice outside area for dogs. "
United States
Lisa W.
The price is CA $275
CA $630 total
includes taxes & fees
May 18 - May 19
Hidden Gem on Hidden Valley Lane

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (977 reviews)
"Beautiful hotel!"
United States
David
The price is CA $147
CA $160 total
includes taxes & fees
May 31 - Jun 1
Courtyard by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (856 reviews)
"great rooms!"
United States
Justine Patrick E.F.
The price is CA $127
CA $139 total
includes taxes & fees
May 19 - May 20
Fairfield Inn & Suites by Marriott Winchester

Relax Inn Motel

Relax Inn Motel
2.0 star property
Front Royal
8.2 out of 10, Very good, (274 reviews)
"The owners/managers are delightful. The room was very nice with excellent bedding. I look forward to staying there again "
United States
Sarah
The price is CA $89
CA $99 total
includes taxes & fees
May 19 - May 20
Relax Inn Motel

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Harpers Ferry
9.8 out of 10, Exceptional, (47 reviews)
"The house was great, clean, beautiful setting."
United States
Brandon M.
The price is CA $300
CA $722 total
includes taxes & fees
May 28 - May 29
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Upperville Hotel Reviews

Find out more about Upperville

Upperville Villas information

Number of reviews
10,679
Accommodation
7 Villas
Lowest Price
CA $99
Highest Price
CA $722

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.

Explore a world of travel with Expedia