Compare Upperville Cottage Rentals

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Featured Cottages in Upperville

CEDAR LANE - Private Cottage, Sophisticated Country Charm

CEDAR LANE - Private Cottage, Sophisticated Country Charm

Middleburg VA
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Hamilton VA
$344 nightly
The price is $392 total per night
$392 total
Apr 13 - Apr 14
Total with taxes and fees
Guests of this cottage have access to a hot tub.
Pool
Hot Tub
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

Purcellville VA
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Purcellville VA
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA
$367 nightly
The price is $394 total per night
$394 total
Apr 19 - Apr 20
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Pet friendly
The Vue - Mountain Top hot tub overlooking the Shenandoah River

The Vue - Mountain Top hot tub overlooking the Shenandoah River

Front Royal VA
$440 nightly
The price is $485 total per night
$485 total
May 3 - May 4
Total with taxes and fees
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.

Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.

Catharpin VA
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
Country Elegance overlooking the Shenandoah River

Country Elegance overlooking the Shenandoah River

Front Royal VA
At this cottage, guests have access to a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly cottage include a garden and barbecue grills.
Hot Tub
Kitchen
Cottage at Gray Fox- Many Attraction- Pet Friendly

Cottage at Gray Fox- Many Attraction- Pet Friendly

Harpers Ferry WV
Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This cottage also has barbecue grills.
Hot Tub
Kitchen
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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.

Hotel Options in Upperville

    Lansdowne Resort and Spa

    Lansdowne Resort and Spa

    44050 Woodridge Pkwy Leesburg VA
    $265 nightly
    The price is $302 total per night from Apr 26 to Apr 27
    $302 total
    Apr 26 - Apr 27
    Total with taxes and fees
    8.8/10 Excellent! (1,001 reviews)
    Salamander Resort And Spa

    Salamander Resort And Spa

    500 North Pendleton Street Middleburg VA
    $596 nightly
    The price is $679 total per night from May 10 to May 11
    $679 total
    May 10 - May 11
    Total with taxes and fees
    9.2/10 Wonderful! (389 reviews)
    Hilton Garden Inn Dulles North

    Hilton Garden Inn Dulles North

    22400 Flagstaff Plaza Ashburn VA
    $121 nightly
    The price is $138 total per night from Apr 19 to Apr 20
    $138 total
    Apr 19 - Apr 20
    Total with taxes and fees
    8.4/10 Very Good! (1,001 reviews)

Cottages

Book a cottage in Upperville
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Upperville. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Upperville better.

Cottage apartments in Upperville range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Upperville
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Upperville and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Upperville cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Upperville. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Upperville Cottages essential information

Accommodation
89 Cottages
Lowest Price
$138
Highest Price
$679
Popular accommodation
CEDAR LANE - Private Cottage, Sophisticated Country Charm, The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!, Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond, Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond, 18th Century Stone Cottage minutes from historic Middleburg, The Vue - Mountain Top hot tub overlooking the Shenandoah River, Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC. , Country Elegance overlooking the Shenandoah River, Cottage at Gray Fox- Many Attraction- Pet Friendly