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Stephenson Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Stephenson vacation rentals

Exterior

1. 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)
"Nice house in a good central location. "
United States
Mitchell V.
The price is ￥31,165
￥54,748 total
includes taxes & fees
Aug 2 - Aug 3
Cameron Charmer pristine downtown apt with double master suites
Smart TV, fireplace

2. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is ￥34,943
￥61,704 total
includes taxes & fees
Aug 2 - Aug 3
Scarborough Fair walk to downtown two story apt
Smart TV

3. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (17 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is ￥29,119
￥50,647 total
includes taxes & fees
Aug 2 - Aug 3
Nostalgia Lane in the heart of the city
Dining

4. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (10 reviews)
"Great location…"
United States
John P.
The price is ￥32,267
￥58,850 total
includes taxes & fees
Aug 16 - Aug 17
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Terrace/patio

5. Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveler
The price is ￥15,740
￥27,643 total
includes taxes & fees
Aug 9 - Aug 10
Cozy English Basement Apt quiet but close to downtown
Interior

6. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
The price is ￥20,462
￥33,883 total
includes taxes & fees
Aug 30 - Aug 31
Pretty Little Apt by the Train II
Terrace/patio

7. 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 ￥26,512
￥52,862 total
includes taxes & fees
Aug 9 - Aug 10
Forest 2BR chalet w/ hot tub & backyard
Terrace/patio

8. 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 ￥23,031
￥49,572 total
includes taxes & fees
Aug 9 - Aug 10
Stone chalet w/ views & hot tub
Terrace/patio

9. 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 ￥26,028
￥48,697 total
includes taxes & fees
Aug 20 - Aug 21
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
TV, fireplace, offices

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
8.2 out of 10, Very Good, (19 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is ￥21,444
￥48,910 total
includes taxes & fees
Aug 2 - Aug 3
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Exterior

11. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (24 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is ￥16,291
￥44,239 total
includes taxes & fees
Aug 4 - Aug 5
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Smart TV, fireplace, video games, DVD player

12. 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, (84 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 ￥20,541
￥54,045 total
includes taxes & fees
Aug 12 - Aug 13
Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Dining

13. ~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, (96 reviews)
"Great property, host was very communicative!"
United States
Lizzy H.
The price is ￥29,119
￥60,432 total
includes taxes & fees
Aug 19 - Aug 20
~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake.
Dining

14. Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Harpers Ferry
9.8 out of 10, Exceptional, (48 reviews)
"Very relaxing great time."
United States
Alfred A.
The price is ￥49,738
￥103,863 total
includes taxes & fees
Aug 12 - Aug 13
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Terrace/patio

15. 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
9.8 out of 10, Exceptional, (10 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 ￥22,823
￥28,907 total
includes taxes & fees
Aug 12 - Aug 13
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Dining

16. Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
Harpers Ferry
9.8 out of 10, Exceptional, (23 reviews)
"House was very clean and the hosts were responsive and very nice! Great place for a quiet weekend getaway. "
United States
Nicole H.
The price is ￥30,221
￥76,377 total
includes taxes & fees
Sep 1 - Sep 2
Log Cabin w/ Hot Tub & Waterfront Patio!
Outdoor dining

17. Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (26 reviews)
"Great house! The view was amazing. Having extra kayaks was great. If you plan to use the lake, plan for 10 per person per day, that was an added expense for a family of six! "
United States
Amy H.
The price is ￥42,655
￥107,781 total
includes taxes & fees
Aug 4 - Aug 5
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Terrace/patio

18. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (1 review)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveler
The price is ￥11,805
￥33,680 total
includes taxes & fees
Aug 27 - Aug 28
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Outdoor dining

19. 3BR cabin w/ hot tub & game room

3BR cabin w/ hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"While there was something left to be desired by the kitchen utensils and cookware, this place is located off the beaten path in a beautiful mountainside area. Definitely worth the price. Just bring your own pot holders and pizza cutter if you plan on having pizza lol. "
United States
Tyrell O.
The price is ￥34,482
￥61,379 total
includes taxes & fees
Aug 20 - Aug 21
3BR cabin w/ hot tub & game room
Terrace/patio

20. Cozy Bear-Themed Mountain Cabin in Harpers Ferry with Relaxing Jacuzzi Hot Tub

Cozy Bear-Themed Mountain Cabin in Harpers Ferry with Relaxing Jacuzzi Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (64 reviews)
"The hosts were very friendly and the house was just as expected. Our family of 4 and furry friend ba sa great time! "
United States
Tyler W.
The price is ￥74,414
￥124,637 total
includes taxes & fees
Aug 15 - Aug 16
Cozy Bear-Themed Mountain Cabin in Harpers Ferry with Relaxing Jacuzzi Hot Tub
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

Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"The staff was very friendly, however our King bed room was a little small."
Oren 1-night trip
Posted 1 hour ago
Quality Inn Winchester

Find out more about Stephenson

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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.