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Recommended hotels in Upperville

1. Goodstone Inn & Restaurant

Goodstone Inn & Restaurant
4.0 star property
Middleburg
9.6 out of 10, Exceptional, (58 reviews)
"Charming and delicious and perfect getaway!! Minutes from middleburg and yet the countryside was glorious!!!"
United States
Karlyn
$385 nightly
The price is $439
Nov 30 - Dec 1
Total with taxes and fees
Goodstone Inn & Restaurant

2. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (68 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
$368 nightly
The price is $395
Nov 15 - Nov 16
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg

3. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
$321 nightly
The price is $354
Nov 15 - Nov 16
Total with taxes and fees
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

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

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Middleburg
9.6 out of 10, Exceptional, (29 reviews)
"Easy to get in and out, and the property was clean and tidy!"
United States
Cameron H.
$226 nightly
The price is $258
Nov 8 - Nov 9
Total with taxes and fees
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

5. DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1,002 reviews)
"It was a nice stay.. third time staying… relaxing and peaceful"
United States
Adrian
$120 nightly
The price is $132
Dec 6 - Dec 7
Total with taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows

6. L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.4 out of 10, Exceptional, (180 reviews)
"Everything about this special place is incredible."
United States
James
$320 nightly
The price is $353
Nov 9 - Nov 10
Total with taxes and fees
L'Auberge Provencale Inn & Restaurant

7. Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.2 out of 10, Wonderful, (1,001 reviews)
"The hotel was really well maintained inside and out! Room was super-clean."
United States
Tammy
$118 nightly
The price is $132
Dec 3 - Dec 4
Total with taxes and fees
Hampton Inn Front Royal

8. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (22 reviews)
"Perfect for a mother and daughter get away. Peaceful and quiet. Short distance to Middleburg. Looking forward to staying here again. Already planning another trip with the whole family at Thanksgiving!"
United States
Denise B.
$518 nightly
The price is $591
Dec 1 - Dec 2
Total with taxes and fees
Spacious Modern Home on Middleburg Horse Farm

9. Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.6 out of 10, Exceptional, (147 reviews)
"I loved the charm of the inn, and I had my best sleep of the week on their comfortable beds. The breakfast the next morning was delicious!! A great value for a bed and breakfast!!"
United States
Gary
$259 nightly
The price is $295
Dec 6 - Dec 7
Total with taxes and fees
Inn at Evergreen

10. Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (47 reviews)
"Nice cabin for couples. The bed was comfy and had all basic necessities for making meals. We will definitely stay again."
United States
Carla M.
$218 nightly
The price is $240
Nov 8 - Nov 9
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road

11. TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (616 reviews)
"Cleaned, maintained hotel near many conveniences."
United States
JoEllen
$137 nightly
The price is $151
Nov 29 - Nov 30
Total with taxes and fees
TownePlace Suites by Marriott Front Royal

12. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.6 out of 10, Exceptional, (1,147 reviews)
"Nice hotel. I would stay here again."
United States
Kenneth
$99 nightly
The price is $111
Nov 29 - Nov 30
Total with taxes and fees
Comfort Inn & Suites Winchester

13. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.6 out of 10, Exceptional, (14 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
$294 nightly
The price is $325
Nov 17 - Nov 18
Total with taxes and fees
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

14. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2,262 reviews)
"Great place to stay the night after a long drive"
United States
lucy
$104 nightly
The price is $115
Nov 8 - Nov 9
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester

15. Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 star property
Front Royal
6.4 out of 10, (1,000 reviews)
"Great breakfast nice room"
Netherlands
pieter
$60 nightly
The price is $67
Nov 11 - Nov 12
Total with taxes and fees
Baymont by Wyndham Front Royal Near Shenandoah National Park

16. Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very good, (922 reviews)
"Great hotel"
United States
Michael
$84 nightly
The price is $93
Nov 9 - Nov 10
Total with taxes and fees
Holiday Inn Express Winchester South-Stephens City by IHG

17. Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,001 reviews)
"Great location and comfortable room."
United States
Amelia
$72 nightly
The price is $76
Nov 17 - Nov 18
Total with taxes and fees
Super 8 by Wyndham Front Royal Near Shenandoah National Park

18. Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
Winchester
9.4 out of 10, Exceptional, (48 reviews)
"Clean rooms , friendly staff."
United States
Jean
$88 nightly
The price is $100
Nov 15 - Nov 16
Total with taxes and fees
Home2 Suites By Hilton Winchester

19. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (968 reviews)
"Great place to stay in Winchester."
United States
Thomas
$93 nightly
The price is $103
Nov 8 - Nov 9
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester

20. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (1,004 reviews)
"Clean room, great staff, good parking and free breakfast"
United States
Albert
$65 nightly
The price is $73
Dec 6 - Dec 7
Total with taxes and fees
Spark by Hilton Winchester
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.

Learn more about Upperville

Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.

A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

Top reviews in Upperville

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