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Vacation Rentals in Upperville, VA and nearby

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    From
    $195
    / Night
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    Upperville
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Overview

    The following rentals are within 20 miles of Upperville, Virginia.

    From
    $220
    / Night
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    1 / 13
    5 of 5 stars (1) Excellent
    Purcellville
    5 Bedrooms, 1 Bathroom, Sleeps 10
    other travelers have booked this property
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    $140
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    1 / 44
    5 of 5 stars (20) Excellent
    Front Royal
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travelers have booked this property
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    $295
    / Night
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    1 / 36
    4.5 of 5 stars (7) Very good
    Front Royal
    3 Bedrooms, 5 Bathrooms, Sleeps 20
    other travelers have booked this property
    Overview Reviews (7) Make Inquiry
    Overview Reviews (7)
    Amenities & Details
    • Wi-Fi
    • Staffed Property
    • Pool Table
    • Air Conditioning
    • Hot Tub
    • Game Room
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ideal for groups, small family gatherings or a romantic escape! The Celebration retreat is located just under an hours drive from Washington DC on 5 beautiful acres with breathtaking views! Escape the hustle & bustle of the city. Imagine stunning sunrises, sunsets, entertainment, amazing local... View all property information
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    Location Information
    Front Royal, Virginia 22630
    5 of 5 stars Reviewed June 22, 2015
    The suites are beautifully furnished,the jacuzzi is relaxing & the kitchen is top of the line! We really enjoyed the theater & white robes! You leave feeling like a special type...
    2 of 5 stars Reviewed May 18, 2015
    We booked the celebrations retreat for my sister's bachelorette weekend. Upon arrival the house was pretty dirty. Margarita salt all over the counters, had not been swept, dirty...
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    $210
    / Night
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    1 / 11
    5 of 5 stars (4) Excellent
    Winchester
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    other travelers have booked this property
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    Overview Reviews (4)
    Amenities & Details
    • Refrigerator
    • DVD Player
    • TV
    • Washer
    • Dryer
    • Internet Access
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Step back in time with a stay in the historic, completely renovated Peter Miller house, esta. 1802. It is like having the run of your very own Bed and Breakfast in the heart of historic Old Town Winchester. The three bedroom (1 K, 1 Q & 2 F) home has been restored and furnished with antiques and... View all property information
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    Location Information
    Winchester, Virginia 22601
    5 of 5 stars Reviewed May 18, 2015
    This was our second stay at the Peter Miller house and it was even better this time than the last time. The new king sized bed in the front bedroom is a beautiful addition to the...
    5 of 5 stars Reviewed April 14, 2015
    We walked into this house and promptly fell in love. This historic home is filled with charm, hospitality and beautiful antiques. The bedrooms are spacious and comfortable, the...
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    $275
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    1 / 24
    4.5 of 5 stars (3) Very good
    Front Royal
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    other travelers have booked this property
    Overview Reviews (3) Make Inquiry
    Overview Reviews (3)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful mountain home located on 18 acres. There is $3,000 sq ft of living space! All log home. Prime location!!! Located next to Skyline Drive entrance and right down the road from Skyline Caverns. Also right down the road from a local tubing, kayak, and canoe rental shop and public river... View all property information
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    Location Information
    Front Royal, Virginia 22630
    4 of 5 stars Reviewed March 3, 2015
    I rented this cabin with a group of friends for my husband's birthday. We had 8 guests staying overnight and we had another ten or so people come over during the day to celebrate...
    5 of 5 stars Reviewed October 21, 2014
    Six of us stayed at this house for a long weekend. It's a big, beautiful house from the outside and inside. There is plenty of room and it's very inviting. Fyi...one of the...
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    $220
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    1 / 10
    5 of 5 stars (1) Excellent
    Purcellville
    4 Bedrooms, 2 Bathrooms, Sleeps 10
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Air Conditioning
    • Gym
    • Mountain Views
    • Deck
    • Private Outdoor...
    • Internet Access
    • Grill
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    A Rustic log cabin for the Romantic, country getaway in the heart of Northern Virginia's Wine Country. View all property information
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    Location Information
    Purcellville, Loudoun County 20132
    5 of 5 stars Reviewed February 16, 2015
    Very clean and comfortable rooms. Our hosts could not have been friendlier! We so enjoyed our stay for Valentines weekend. It was a quiet cozy atmosphere ono a blustery...
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    $195
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    Purcellville
    3 Bedrooms, 3 Bathrooms, Sleeps 7
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Washer
    • Hot Tub
    • Wi-Fi
    • Deck
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nestled on the side of a secluded mountain in the heart of wine country in Loudoun County. Three private suites are available - The Eagle's Nest, with private balcony, The Falcon's Nest and the Owl's Nest. All feature a private bathroom and access to a common modern kitchen and living space.... View all property information
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    Location Information
    Purcellville, Loudoun County 20132
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    $345
    / Night
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    1 / 13
    3 of 5 stars (1) Average
    Berryville
    4 Bedrooms, 2 Bathrooms, Sleeps 16
    other travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Mountain Views
    • Porch
    • Air Conditioning
    • Refrigerator
    • Stove
    • Patio
    • Washer
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Union General Philip Sheridan squared off with Confederate General Jubal Early in the Battle of Berryville, the battle line falling along a ridge just behind the spot where this beautifully restored guest house now sits. The Philip Sheridan Cottage is a four-bedroom, two-bath guest house on a... View all property information
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    Location Information
    Berryville, Virginia 22611
    3 of 5 stars Reviewed December 6, 2014
    Very clean and comfortable with well furnished bedrooms. No TV or WiFi. We stayed during a cold weather snap of Thanksgiving 2014 that included snowfall so that we could not...
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    $395
    / Night
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    Berryville
    6 Bedrooms, 3 Bathrooms, Sleeps 19
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Porch
    • Air Conditioning
    • Parking
    • Soap/Shampoo...
    • Towels Provided
    • Mountain Views
    • Stove
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Confederate General Jubal Early squared off against Union General Philip Sheridan in the Battle of Berryville, fought just a stone's throw away from where this beautifully restored guest house now sits. The Jubal Early Cottage is a six-bedroom, 2.5-bath guest house nestled in a secluded, mostly... View all property information
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    Location Information
    Berryville, Virginia 22611
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    $400
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    1 / 9
    5 of 5 stars (4) Excellent
    Summit Point, WV
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (4) Make Inquiry
    Overview Reviews (4)
    Amenities & Details
    • Dryer
    • Satellite TV
    • Deck
    • Washer
    • Wi-Fi
    • Fireplace
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    We are listed here on FlipKey/TripAdvisor just to gather reviews. Google us 'Ruby Summit Point' to find us. Stay in a wonderful 3 bedroom house in Summit Point just minutes from the track! Bought, renovated and furnished in winter 2014. Multiple garage spaces and honor tools. Outdoor... View all property information
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    Location Information
    Summit Point, West Virginia 25446
    5 of 5 stars Reviewed August 1, 2015
    I don't often take the time to write online reviews but our extended family (three-generations) had such a great weekend staying at Ruby Summit Point. It truly felt like home away...
    5 of 5 stars Reviewed June 16, 2015
    Ruby Summit Point is a great place to say with a group of friends over a track weekend. Very close to the track so no time wasted commuting to distant hotels. Very nicely upgraded...
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    $1,100
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    1 / 24
    5 of 5 stars (1) Excellent
    Leesburg
    8 Bedrooms, 6 Bathrooms, Sleeps 25
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Housekeeping...
    • Pool Table
    • Wi-Fi
    • Air Conditioning
    • Swingset
    • Private Outdoor...
    • Hot Tub
    • Game Room
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    We do not allow weddings, events, or parties on our property. This stunning French Provencal Estate sits on 3 premium acres and boast nearly 12,000 square feet. No detail has been spared in the design of this home. This is truly a family home- build and designed with family gatherings in mind.... View all property information
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    Location Information
    Leesburg, Loudoun County 20176
    5 of 5 stars Reviewed May 26, 2015
    This house is just amazing, so comfortable, and luxe. No detail is spared. The location is so close to Dulles airport and around great wineries, horse back riding and not far from...
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    From
    $200
    / Night
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    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Porch
    • Refrigerator
    • Linens Provided
    • Dryer
    • Washer
    • Stove
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    We use ALL organic non-scented cleaning products. Our home is within Winchester city limits but has the peacefulness of the country. If it's a quiet safe neighborhood you're looking for you've found it! The perfect spot to rest and regroup amongst nature. Come enjoy the beauty of the Shenandoah... View all property information
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    Location Information
    Winchester, Virginia 22601
    From
    $199
    / Night
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    1 / 21
    Front Royal
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Water Views
    • Internet Access
    • Mountain Views
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Rolling River Farm (com) Private 100 Acre Riverfront Paradise surrounded by water on three sides due to its location on a full bend in the legendary Shenandoah River. -Just one hour from Dulles Airport and the Washington Capitol Beltway -Just one and a quarter hours from Capitol Hill (believe it... View all property information
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    Location Information
    Front Royal, Virginia 22630
    From
    $295
    / Night
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    Berryville
    3 Bedrooms, 2 Bathrooms, Sleeps 13
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Mountain Views
    • Refrigerator
    • Linens Provided
    • Porch
    • Air Conditioning
    • Parking
    • Patio
    • Stove
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    John Wayne, the namesake of this quaint guest house, was among many esteemed guests to the Rosemont Estate during its rich 200 year history. The John Wayne Lodge, built in the early 20th century, is surrounded by rare, historic trees and is just a stone's throw from the battle lines of the Battle... View all property information
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    Location Information
    Berryville, Virginia 22611
    From
    $165
    / Night
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    Berryville
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Linens Provided
    • Air Conditioning
    • Towels Provided
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This is a guest bedroom within the Civil War Union Guest House (also known as the Philip Sheridan Guest Cottage). The bedroom sleeps 2-4 people with a private bath. One queen bed, and one set of single bunk beds. Located in historic Berryville, VA on the site of a Civil War battlefield, and... View all property information
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    Location Information
    Berryville, Virginia 22611
    From
    $175
    / Night
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    1 / 12
    Front Royal
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Fireplace
    • Washer
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Deck
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our 9 cabins are located near Front Royal, Virginia, the Canoe Capital of Virginia and where Skyline Drive begins... Only 10 miles from downtown Front Royal and 10 miles off Interstate I-66 – and just 60 miles directly west of Washington, DC. Hot Tub Heaven Vacation Cabins, offer 9 cabins... View all property information
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    Location Information
    Front Royal, Virginia 22630
    From
    $875
    / Night
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    1 / 20
    Leesburg
    6 Bedrooms, 4 Bathrooms, Sleeps 18
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Patio
    • DVD Player
    • Washer
    • Air Conditioning
    • Internet Access
    • Stereo System
    • Dryer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This luxury sun lit home is in Leesburg,Virginia just 40 miles northwest of our capital -Washington,DC ! Enjoy family gatherings,holiday vacations,corporate retreats/team building,girls getaways,moms'retreats,health -yoga-silent-healing workshop weekends on this gorgeous 25 acre fully modernize... View all property information
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    Location Information
    Leesburg, Loudoun County
    From
    $175
    / Night
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    1 / 12
    Front Royal
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Fireplace
    • Satellite TV
    • Washer
    • Hot Tub
    • Deck
    • Stereo System
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our 9 cabins are located near Front Royal, Virginia, the Canoe Capital of Virginia and where Skyline Drive begins... Only 10 miles from downtown Front Royal and 10 miles off Interstate I-66 – and just 60 miles directly west of Washington, DC. Hot Tub Heaven Vacation Cabins, offer 9 cabins... View all property information
    Make Inquiry
    Location Information
    Front Royal, Virginia 22630
    From
    $875
    / Night
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    1 / 20
    Leesburg
    6 Bedrooms, 4 Bathrooms, Sleeps 18
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Patio
    • Washer
    • Internet Access
    • Dryer
    • Satellite TV
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This luxury sun lit home is in Leesburg,Virginia just 40 miles northwest of our capital -Washington,DC ! Enjoy family gatherings,holiday vacations,corporate retreats/team building,girls getaways,moms'retreats,health -yoga-silent-healing workshop weekends on this gorgeous 25 acre fully modernize... View all property information
    Make Inquiry
    Location Information
    Leesburg, Loudoun County
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