Compare Upperville Cottage Rentals

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Featured Cottages in Upperville

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.
Bear Mountain Cottage

Bear Mountain Cottage

Paeonian Springs VA
At this cottage, guests have access to features like laundry facilities.
Hattingh Equine Rescue Launches Farm Cottage Stay to Support Rescued Horses

Hattingh Equine Rescue Launches Farm Cottage Stay to Support Rescued Horses

Purcellville VA
Guests staying at this cottage can enjoy an outdoor pool, a water dispenser, and barbecue grills. This smoke-free cottage also has a garden.
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

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

Hamilton VA
$347 nightly
The price is $396 total per night
$396 total
Jul 14 - Jul 15
Total with taxes and fees
Guests of this cottage have access to a hot tub.
Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!

Harpers Ferry WV
$365 nightly
The price is $407 total per night
$407 total
Jul 15 - Jul 16
Total with taxes and fees
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. Limited parking is available.
Hunt Country cottage in Upperville!

Hunt Country cottage in Upperville!

Upperville VA
At this cottage, guests have access to features like laundry facilities.
Washer
Dryer
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA
$369 nightly
The price is $396 total per night
$396 total
Jul 14 - Jul 15
Total with taxes and fees
Guests staying at this cottage have access to a garden and barbecue grills.
Historical cottage in the town of Paris

Historical cottage in the town of Paris

Paris VA
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
A Restored Wagon Barn On A 1790's Farm.

A Restored Wagon Barn On A 1790's Farm.

Purcellville VA
At this cottage, guests have access to features like laundry facilities. This adults-only cottage also has a garden.
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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

    TRU By Hilton Winchester

    TRU By Hilton Winchester

    118 Mercedes Court Winchester VA
    $81 nightly
    The price is $90 total per night from Jul 26 to Jul 27
    $90 total
    Jul 26 - Jul 27
    Total with taxes and fees
    9.2/10 Wonderful! (1,031 reviews)
    Lansdowne Resort and Spa

    Lansdowne Resort and Spa

    44050 Woodridge Pkwy Leesburg VA
    $275 nightly
    The price is $314 total per night from Aug 5 to Aug 6
    $314 total
    Aug 5 - Aug 6
    Total with taxes and fees
    8.8/10 Excellent! (1,009 reviews)
    Spark by Hilton Winchester

    Spark by Hilton Winchester

    150 Wingate Dr Winchester VA
    $65 nightly
    The price is $73 total per night from Jul 26 to Jul 27
    $73 total
    Jul 26 - Jul 27
    Total with taxes and fees
    9/10 Wonderful! (1,011 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
92 Cottages
Lowest Price
$73
Highest Price
$407
Popular accommodation
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond, Bear Mountain Cottage, Hattingh Equine Rescue Launches Farm Cottage Stay to Support Rescued Horses, The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!, Cottage w/ Hot Tub and 100-Mile Valley Views!, Hunt Country cottage in Upperville!, 18th Century Stone Cottage minutes from historic Middleburg, Historical cottage in the town of Paris, A Restored Wagon Barn On A 1790's Farm.