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Stephenson Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Stephenson vacation rentals

A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

1. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
10.0 out of 10, Exceptional, (2 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is CA $205
CA $364 total
includes taxes & fees
Sep 8 - Sep 9
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A two-story house with a front porch, a mailbox, and a number plate.

2. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (9 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
The price is CA $274
CA $486 total
includes taxes & fees
Sep 14 - Sep 15
Cameron Charmer pristine downtown apt with double master suites
A modern living room with a fireplace, a round coffee table, and a comfortable seating area.

3. Indigo Blue modern open vibe on tree lined street

Indigo Blue modern open vibe on tree lined street
Winchester Historic District
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! The place was very clean and exactly as described. Michele communicated clearly and responded quickly, which made everything easy from check-in to check-out. The location was also perfect—very close to downtown and convenient to everything we wanted to do. We would definitely stay here again and highly recommend it to others!"
United States
Elaina R.
The price is CA $305
CA $565 total
includes taxes & fees
Sep 7 - Sep 8
Indigo Blue modern open vibe on tree lined street

4. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (43 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
The price is CA $194
CA $421 total
includes taxes & fees
Sep 7 - Sep 8
Stone chalet w/ views & hot tub
A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

5. Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
7.8 out of 10, Good, (20 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is CA $189
CA $429 total
includes taxes & fees
Sep 14 - Sep 15
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

6. Forest 2BR chalet w/ hot tub & backyard

Forest 2BR chalet w/ hot tub & backyard
Gerrardstown
9.6 out of 10, Exceptional, (5 reviews)
"Just an overnight stay. On our way back home from northern New York. The place was nice. It is peaceful sitting on the deck. The check in process was a little tedious with various emails and downloads required. The Backstep is a little sketchy. Be careful walking in. Overall the place was nice"
United States
John Z.
The price is CA $228
CA $463 total
includes taxes & fees
Sep 8 - Sep 9
Forest 2BR chalet w/ hot tub & backyard
A hot tub with a wooden deck, a wooden cabin with large windows, and a deck chair.

7. Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Gerrardstown
9.0 out of 10, Wonderful, (12 reviews)
"We had a fabulous time and highly recommend this rental."
United States
Amber H.
The price is CA $265
CA $474 total
includes taxes & fees
Sep 30 - Oct 1
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
A hot tub outside a building with a view of autumn trees.

8. 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, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is CA $138
CA $477 total
includes taxes & fees
Sep 10 - Sep 11
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub in front of a wooden cabin with a tree in the background.

9. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (13 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is CA $201
CA $254 total
includes taxes & fees
Sep 8 - Sep 9
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A deck with outdoor seating and a lake view.

10. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
9.8 out of 10, Exceptional, (9 reviews)
"Had a wonderful stay here. Shaun was an excellent host with easy communication. Peaceful location with a lake! Convenient to Harper’s Ferry. "
United States
Liz P.
The price is CA $44
CA $328 total
includes taxes & fees
Sep 13 - Sep 14
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A rustic cabin interior with a leather sofa, wooden beams, and mounted animal heads.

11. Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.

Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Cross Junction
9.6 out of 10, Exceptional, (87 reviews)
"The best, peaceful, fun, ATV wheeling, target practice, grilling, great kitchen supplies and plenty of space for the family Would stay again"
United States
Lisa G.
The price is CA $156
CA $441 total
includes taxes & fees
Sep 16 - Sep 17
Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
A living room with a dining table, chairs, a sofa, and a television.

12. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (24 reviews)
"Host let us in a bit early which was nice!"
United States
John
The price is CA $166
CA $304 total
includes taxes & fees
Sep 7 - Sep 8
Quaint Mini Cottage in Shepherdstown - Walking Distance
A modern building with a patio area, a fire pit, and a view of a river and forest.

13. Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
10.0 out of 10, Exceptional, (1 review)
"Great views, house is clean and cozy with a fireplace"
United States
Matthew P.
The price is CA $138
CA $477 total
includes taxes & fees
Sep 7 - Sep 8
Cabin at the Gap | You Won't Believe the View!
A hot tub in a forested area with a rocky ground and trees.

14. The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (5 reviews)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
The price is CA $138
CA $508 total
includes taxes & fees
Sep 17 - Sep 18
The Blue Jay | New House in the Woods w/ Hot Tub
A spacious room with a large dining table, white chairs, and a ceiling fan.

15. ~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake

~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake
Harpers Ferry
10.0 out of 10, Exceptional, (102 reviews)
"Great property, host was very communicative!"
United States
Lizzy H.
The price is CA $235
CA $509 total
includes taxes & fees
Sep 7 - Sep 8
~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake
A cozy cabin interior with a wooden interior, a sofa, a table, and a view through large windows.

16. Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (76 reviews)
"This was an absolutely amazing stay. Beautiful location, extremely comfortable. Well stocked kitchen. Wonderful hot tub. Perfection for a getaway."
United States
Andrew L.
The price is CA $138
CA $513 total
includes taxes & fees
Sep 10 - Sep 11
Blue Ridge Getaway - Sunset Views, A.T. Access
A room with a large window overlooking a forested area.

17. Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (20 reviews)
"We had a wonderful stay. The communication and the guestbook were wonderful. The view was gorgeous and the property was clean and comfortable. "
United States
Kaitlyn C.
The price is CA $138
CA $548 total
includes taxes & fees
Sep 8 - Sep 9
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
A hot tub with a view of a forested landscape during sunset.

18. 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, (26 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
United States
Anonymous traveller
The price is CA $138
CA $525 total
includes taxes & fees
Sep 16 - Sep 17
Cottage w/ Hot Tub and 100-Mile Valley Views!
A wooden deck with two Adirondack chairs and a small table, two wine glasses on the table, surrounded by lush green trees.

19. 4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.6 out of 10, Exceptional, (9 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is CA $166
CA $607 total
includes taxes & fees
Sep 22 - Sep 23
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
A hot tub on a wooden deck with an American flag, string lights, and a view of the landscape.

20. Large Glamper w/ Hot Tub and full bathroom-sleep 6

Large Glamper w/ Hot Tub and full bathroom-sleep 6
Capon Bridge
9.8 out of 10, Exceptional, (25 reviews)
"I can't express enough how appreciative we are to the owner and manager. Best time I've had in years. "
United States
Mary
The price is CA $153
CA $330 total
includes taxes & fees
Sep 15 - Sep 16
Large Glamper w/ Hot Tub and full bathroom-sleep 6
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 Stephenson Hotel Reviews

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"The night shift person in Winchester, VA was amazing. Moved me to another room because of noise!"
Sharon 1-night trip
Posted 2 hours ago
Spark by Hilton Winchester

Find out more about Stephenson

Everything you need to know about Stephenson vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stephenson vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stephenson vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stephenson vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stephenson. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stephenson vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stephenson vacation rentals we have selected for you start as low as CA $307 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stephenson rentals

At Expedia, we put the best Stephenson vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Stephenson rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stephenson vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stephenson. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find vacation rentals in Stephenson?

Yes, we have vacation rentals in Stephenson close to Frederick County Fairgrounds, or you can go with a secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Stephenson?

Mountain View Bungalow in Front Royal: Visitors like this Stephenson vacation home rental. It offers a garden, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Stephenson?

While exploring the area, visit family-friendly sights like Shenandoah Valley Discovery Museum, or get outside and enjoy nature at Mackintosh Fruit Farm. Other places in town to visit include Frederick County Fairgrounds and Red Bud Run.

What are vacation rentals like in Stephenson?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Stephenson. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family gatherings.