Hot Upperville Chalet Rates

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Featured Chalets in Upperville

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

Front Royal VA
With a stay at this chalet in Front Royal, you'll be on a river, within a 15-minute drive of Shenandoah National Park and Blue Ridge Arts Council and ...
Opens in a new windowBear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry WV
The price is AU$497 per night from 28 Jan to 29 Jan
AU$497
28 Jan - 29 Jan 2026
includes taxes & fees
Located in Harpers Ferry, this chalet is in the mountains, within a 10-minute drive of Virginius Island and Harpers Ferry Children's Park.
Opens in a new windowHarpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Cozy w/Fire Pit, Grill, Screened Porch & WiFi

Cozy w/Fire Pit, Grill, Screened Porch & WiFi

Harpers Ferry WV
The price is AU$456 per night from 4 Jan to 5 Jan
AU$456
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at this chalet in Harpers Ferry, you'll be within a 15-minute walk of Shannondale Springs Wildlife Management Area and Shenandoah Lake Beach.
Opens in a new windowCozy w/Fire Pit, Grill, Screened Porch & WiFi
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Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

Harpers Ferry WV
The price is AU$561 per night from 28 Jan to 29 Jan
AU$561
28 Jan - 29 Jan 2026
includes taxes & fees
Located in Harpers Ferry, this chalet is in a rural location, within a 5-minute drive of Shenandoah Lake Beach and Shannondale Springs Wildlife Management ...
Opens in a new windowModern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!
Timber frame chalet with incredible views minutes from Shenandoah National Park.

Timber frame chalet with incredible views minutes from Shenandoah National Park.

Linden VA
With a stay at this chalet in Linden, you'll be in the mountains, within a 15-minute drive of Shenandoah National Park and Fox Meadow Winery.
Opens in a new windowTimber frame chalet with incredible views minutes from Shenandoah National Park.
Family Reunion Escape: Warm 3BR Chalet

Family Reunion Escape: Warm 3BR Chalet

Harpers Ferry WV
Located in Harpers Ferry, this chalet is on a river, within a 15-minute drive of Shenandoah River and Notaviva Vineyards.
Opens in a new windowFamily Reunion Escape: Warm 3BR Chalet
Whitetail Summit - Shenandoah/hot tub/wineries

Whitetail Summit - Shenandoah/hot tub/wineries

Front Royal VA
Located in Front Royal, this chalet is on a lake, within a 10-minute drive of John T Shipe JR Park and Shenandoah River.
Opens in a new windowWhitetail Summit - Shenandoah/hot tub/wineries
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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.

Upperville Chalet Accommodation

We see you over there, so lost in your own thoughts, you might miss your next meeting. You know it’s time to up your holiday game, and we know you’ve been googling things like “ski holidays” and “mountain retreats”. Don’t worry—we won’t tell your boss. We just have a tip for you: If you really want to slay, you need a chalet. Specifically, cheap chalet accommodation in Upperville.

A budget chalet hotel in Upperville is the perfect new topic for your office chit-chat, but unlike that office retreat, there will be no trust falls. You will find all sorts of adventurous activities on offer in Upperville, but none of them will involve your coworkers having to catch you (at least we hope not). Outside, nature awaits, with endless trails and endless fun. Inside, you’ll find all the right amenities for recharging after an active day, from luxurious linens to fully equipped kitchens.

Speaking of kitchens, chalet hotels in Upperville have everything you need for a romantic getaway. Cook up a candlelit dinner and open that perfectly chilled bottle of red. A crackling fireplace and the amazing views of Upperville out your picture window will do the rest.

Our deals practically move mountains, bringing cheap ski chalets and more to you right where you sit. Yes, you’ll have to pack eventually, but for now, browse our sweet selection of Upperville chalets and start dreaming. After all, didn’t your mum always tell you that you can be anything you want to be? Well, you want to be on holiday in Upperville, and it’s time to make it happen.

Upperville Chalets essential information

Accommodation
8 Chalets
Lowest Price
AU$156
Highest Price
AU$941
Popular accommodation
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)
, Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI, Cozy w/Fire Pit, Grill, Screened Porch & WiFi, Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!, Timber frame chalet with incredible views minutes from Shenandoah National Park., Family Reunion Escape: Warm 3BR Chalet, Whitetail Summit - Shenandoah/hot tub/wineries

Top trending hotels in Upperville

Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy Leesburg VA
Fully refundableReserve now, pay when you stay
The price is AU$360 per night from 30 Dec to 31 Dec
AU$360
30 Dec - 31 Dec
includes taxes & fees
Located in Leesburg, Lansdowne Resort and Spa is a 1-minute drive from The Golf Club at Lansdowne and 6 minutes from Village at Leesburg.
Opens in a new windowLansdowne Resort and Spa
Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

3 out of 5
22400 Flagstaff Plaza Ashburn VA
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 3 Jan to 4 Jan
AU$156
3 Jan - 4 Jan 2026
includes taxes & fees
Located in Ashburn, Hilton Garden Inn Dulles North is in the business district, within a 10-minute drive of 1757 Golf Club and Ashburn Ice House.
Opens in a new windowHilton Garden Inn Dulles North
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
The price is AU$941 per night from 7 Jan to 8 Jan
AU$941
7 Jan - 8 Jan 2026
includes taxes & fees
Located in Middleburg, Salamander Resort And Spa is in the historical district, within a 15-minute drive of Greenhill Winery & Vineyards and Chrysalis ...
Opens in a new windowSalamander Resort And Spa
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La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$160 per night from 30 Dec to 31 Dec
AU$160
30 Dec - 31 Dec
includes taxes & fees
With a stay at La Quinta Inn & Suites by Wyndham Winchester in Winchester, you'll be in the business district, just a 3-minute walk from Shenandoah University ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Winchester
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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.

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^Subject to availability and chosen travel dates.