Search Upperville Cottage Rentals from CA $315
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Upperville cottages
1. 18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic MiddleburgMiddleburg
10.0 out of 10, Exceptional, (66 reviews)
"A quaint cottage in a beautiful location!"
Mary H.
The price is CA $387
CA $561 total
includes taxes & fees
Oct 13 - Oct 14
2. Woodsy Retreat with a Hot Tub and Seasonal Views!
Woodsy Retreat with a Hot Tub and Seasonal Views!Harpers Ferry
9.8 out of 10, Exceptional, (28 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
Amy P.
The price is CA $241
CA $625 total
includes taxes & fees
Sep 27 - Sep 28
3. Mountain View Cottage | Hot Tub & Game Room
Mountain View Cottage | Hot Tub & Game RoomFront Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
Katia R.
The price is CA $470
CA $1,012 total
includes taxes & fees
Sep 29 - Sep 30
4. Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Art Docko - Lakefront Artist Retreat w/ Hot Tub!Harpers Ferry
10.0 out of 10, Exceptional, (28 reviews)
"With bedrooms and sitting rooms on 3 floors, our 3-generation family enjoyed having space to gather together as well as space for time apart. The decks allowed for additional places to enjoy the beautiful surroundings. Lake access was great for swimming and kayaking."
Lindy K.
The price is CA $220
CA $728 total
includes taxes & fees
Oct 7 - Oct 8
5. Mountain View Cottage with Hot Tub and River Views
Mountain View Cottage with Hot Tub and River ViewsFront Royal
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and certainly return. Our group was 2 couples and 2 children.Everyone had enough space to be comfortable. The view is beautiful so we enjoyed our time at the house. While in the area, we visited Skyline Caverns and the Shenandoah River. I did have a challenging time getting Door Dash to the house. After 30 minutes of seeing the driver in the neighborhood we got in the car to track down the driver. Her cell service was poor so we were unable to communicate. If I ordered...
MaryBeth C.
The price is CA $457
CA $997 total
includes taxes & fees
Sep 29 - Sep 30
6. Mountaintop Cottage | Private Hot Tub
Mountaintop Cottage | Private Hot TubFront Royal
9.8 out of 10, Exceptional, (27 reviews)
"Excellent location and amazing reviews. Would definitely plan to arrive while it’s light out for the first time as the road does get a little rough at the top but we did all make it in 2WD vehicles"
Sara Z.
The price is CA $523
CA $982 total
includes taxes & fees
Sep 27 - Sep 28
7. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-FiBoyce
9.6 out of 10, Exceptional, (39 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
Felice N.
The price is CA $552
CA $1,096 total
includes taxes & fees
Oct 22 - Oct 23
8. Cottage w/ Hot Tub and 100-Mile Valley Views!
Cottage w/ Hot Tub and 100-Mile Valley Views!Harpers Ferry
9.8 out of 10, Exceptional, (27 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
Anonymous traveller
The price is CA $190
CA $609 total
includes taxes & fees
Oct 12 - Oct 13
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.
Find vacation rentals that suit your style
Cabins
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Upperville Hotel Reviews
Microtel Inn & Suites by Wyndham Winchester
10/10 Excellent
Find out more about Upperville
Upperville Cottages information
Number of reviews | 238 |
|---|---|
Accommodation | 101 Cottages |
Lowest Price | CA $315 |
Highest Price | CA $1,096 |
Frequently asked questions
Explore a world of travel with Expedia
- Motels in Winchester
- Front Royal Hotels
- Walk to Top
- B&B in Potomac Falls
- Doubletree by Hilton Front Royal Blue Ridge Shadows
- L'auberge Provencale Inn & Restaurant
- Briar Patch Bed & Breakfast Inn
- Hotels near RdV Vineyards
- Farmstay in Woodville
- Apartments in Winchester
- Spacious Modern Home on Middleburg Horse Farm
- Motels in Fairfax
- Hunters Retreat with High Speed Internet
- B&B in Boyce
- Purcellville Hotels
- Hot Tub Mountain View Dog Friendly Modern Chalet
- Paris Hotels
- Cabin Rentals in Paris
- Farmstay in Bristow
- Condo Rentals in Stephens City
- Linden Hotels
- Marshall Hotels
- Marriott Hotels & Resorts in Linden
- B&B in Manassas City County
- Cabin Rentals in Northern Virginia
- Hotels near Bluemont Vineyard
- Lodges in Riverton
- Middleburg Hotels
- Resorts in Sterling
- Motels in Casanova
- Aldie Hotels
- Hotels near Linden Vineyards
- Apartments in Huntly
- Buckskin Manor
- Hotels near Washington Dulles Intl.
- Motels in Northern Virginia
- B&B in Midland
- Hampton Inn Front Royal
- Farmstay in Paeonian Springs
- Beach Hotel Hotels in Blue Ridge
- Hyatt Hotels in Hamilton
- Apartments in Millwood
- Berryville Hotels
- Front Royal Hilltop Cabin w/ Panoramic Views!
- Cabin Rentals in Elkwood
- Upperville Hotels
- Resorts in Airlie
- B&B in Bristow
- Winchester Hotels
- Markham Hotels
- Motels in Warrenton
- Motels in Gore
- Relax Inn Motel
- Aparthotels in Prince William County
- Apartments in Sterling
- Breathtaking View with an Indoor Pool
- Villas in Orlean
- Villas in Fairfax
- Vacation Homes in Casanova
- Hotels near Stone Tower Winery
- Cabin Rentals in Fairfax
- Pet-Friendly Hotels in Middleburg
- Flights from Toronto (YYZ) to Winchester (WGO)
- Flights from Buffalo (BUF) to Washington (IAD)
- Flights from Montreal (YUL) to Washington (IAD)
- Flights to Syria
- Flights from Toronto (YTZ) to Washington (IAD)
- Flights from Saskatoon (YXE) to Washington (IAD)
- Flights from Calgary (YYC) to Washington (DCA)
- Flights to Boyce
- Flights from San Francisco (SFO) to Washington (IAD)
- Flights from Hamilton
- Flights to Millwood
- Flights from Detroit (DTW) to Washington (IAD)
- Flights from Markham
- Flights to Gainesville
- Flights from Washington Dulles Intl.
- Flights from Toronto (YYZ) to Washington (DCA)
- Flights from Loudoun County
- Flights from Edmonton (YEG) to Washington (DCA)
- Flights from Ronald Reagan Washington National
- Flights from Blue Ridge
- Flights from Toronto (YYZ) to Washington (IAD)
- Flights from Calgary (YYC) to Washington (IAD)
- Flights from Regina (YQR) to Washington (IAD)
- Flights from Vancouver (YVR) to Washington (IAD)
- Flights from Edmonton (YEG) to Washington (IAD)
- Flights from Winnipeg (YWG) to Washington (IAD)
- Flights to Washington Dulles Intl.
- Flights from Ottawa (YOW) to Washington (DCA)
- Flights from Ottawa (YOW) to Washington (IAD)
- Flights to Hamilton
- Porter Airlines Toronto (YTZ) to Washington (IAD) flights