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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select Upperville Apartments

Our top choices for Upperville apartments

Pretty Little Apt by the Train II
Interior

Pretty Little Apt by the Train II

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great time. Love this city"
The price is CA $180
CA $298 total
includes taxes & fees
Sep 22 - Sep 23
Pretty Little Apt by the Train II
The Stock Exchange downtown 3rd floor studio apt
Fridge, microwave, oven, stovetop

The Stock Exchange downtown 3rd floor studio apt

2.0 star property
6.0 out of 10, (1)
The price is CA $138
CA $258 total
includes taxes & fees
Aug 24 - Aug 25
The Stock Exchange downtown 3rd floor studio apt
Rosamond nice downtown studio apt
Interior

Rosamond nice downtown studio apt

8.0 out of 10, Very good, (2)
"Small but appropriately priced."
The price is CA $152
CA $266 total
includes taxes & fees
Aug 28 - Aug 29
Rosamond nice downtown studio apt
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Desk, iron/ironing board, free WiFi, bed sheets

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

9.8 out of 10, Exceptional, (17)
"Cute farm, nice family. Place as advertised. Close to beautiful country and lots of vineyards."
The price is CA $207
CA $378 total
includes taxes & fees
Aug 28 - Aug 29
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
The Blue Door steps from Handley Library
Exterior detail

The Blue Door steps from Handley Library

2.0 star property
7.0 out of 10, Good, (2)
"Perfect. Met all expectations. Small but Great."
The price is CA $160
CA $268 total
includes taxes & fees
Sep 1 - Sep 2
The Blue Door steps from Handley Library
Private apartment on a beautiful private farm!
Property grounds

Private apartment on a beautiful private farm!

10.0 out of 10, Exceptional, (4)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
The price is CA $195
CA $386 total
includes taxes & fees
Aug 27 - Aug 28
Private apartment on a beautiful private farm!
Berryville Bliss: Basement Apartment in welcoming Berryville
Outdoor dining

Berryville Bliss: Basement Apartment in welcoming Berryville

10.0 out of 10, Exceptional, (3)
"Clean, comfortable and close to Historic Rosemont! Pool was incredible!"
The price is CA $252
CA $635 total
includes taxes & fees
Aug 26 - Aug 27
Berryville Bliss: Basement Apartment in welcoming Berryville
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Interior

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

10.0 out of 10, Exceptional, (3)
"Clean, cute, hot water, cool inside. I would stay again!!!"
The price is CA $228
CA $363 total
includes taxes & fees
Sep 3 - Sep 4
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Fridge, microwave, oven, stovetop

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

2.0 star property
8.0 out of 10, Very good, (3)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
The price is CA $192
CA $325 total
includes taxes & fees
Aug 24 - Aug 25
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Scarborough Fair walk to downtown two story apt
Terrace/patio

Scarborough Fair walk to downtown two story apt

9.4 out of 10, Exceptional, (3)
"We stayed here overnight after our trip to Shenandoah. House had everything we needed for a peaceful night. "
The price is CA $307
CA $534 total
includes taxes & fees
Sep 23 - Sep 24
Scarborough Fair walk to downtown two story apt
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Interior

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

The price is CA $304
CA $547 total
includes taxes & fees
Sep 5 - Sep 6
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Nostalgia Lane in the heart of the city
3 bedrooms, iron/ironing board, WiFi, bed sheets

Nostalgia Lane in the heart of the city

8.8 out of 10, Excellent, (10)
"Great location in the heart of Winchester. Walking distance to everything. "
The price is CA $257
CA $462 total
includes taxes & fees
Aug 24 - Aug 25
Nostalgia Lane in the heart of the city
Cozy 1BR Apt Minutes From Skyline Drive!!
Fridge, microwave, oven, stovetop

Cozy 1BR Apt Minutes From Skyline Drive!!

9.6 out of 10, Exceptional, (33)
"The Cozy Apartment was a nice little stay for our trip to the area including great vineyards, great restaurant (Claire's) in Warrenton, and a great experience in one of our nation's best National Parks - Shenandoah National Park. "
The price is CA $168
CA $323 total
includes taxes & fees
Aug 24 - Aug 25
Cozy 1BR Apt Minutes From Skyline Drive!!
Apple Mountain Retreat
Property grounds

Apple Mountain Retreat

10.0 out of 10, Exceptional, (15)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is CA $187
CA $323 total
includes taxes & fees
Aug 24 - Aug 25
Apple Mountain Retreat
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
Exterior

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

9.8 out of 10, Exceptional, (9)
"The entire stay was nothing but exceptional. The host was very informative, knowledgeable, and helped make the stay all it can be and then some."
The price is CA $484
CA $703 total
includes taxes & fees
Aug 28 - Aug 29
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Private kitchen

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

10.0 out of 10, Exceptional, (1)
"Jessica was a wonderful host. Outdoor table was lovely with a great view of a garden with cows as next door neighbors "
The price is CA $191
CA $373 total
includes taxes & fees
Sep 3 - Sep 4
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Historic apartment in Old Town Warrenton, Virginia
Outdoor dining

Historic apartment in Old Town Warrenton, Virginia

9.8 out of 10, Exceptional, (51)
"The property was top notch! It was as comfortable as any 5 star hotels we have stayed in. Upon arrival we took advantage of the outdoor dining area and had drinks before leaving for dinner. The linens were also soft and fluffy. The rooms were beautifully decorated."
The price is CA $210
CA $322 total
includes taxes & fees
Aug 25 - Aug 26
Historic apartment in Old Town Warrenton, Virginia
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.
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Top Upperville Hotel Reviews

Hampton Inn Front Royal

Hampton Inn Front Royal

10/10 Excellent
"Staff was awesome! We had 3 cats with us and they made sure we were all taken care of "
Kelly 2-night trip
Posted 14 hours ago
Hampton Inn Front Royal