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Stephenson Vacation Rentals

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Our top choices for Stephenson vacation rentals

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 $204
CA $363 total
includes taxes & fees
Sep 7 - Sep 8
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

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 $273
CA $483 total
includes taxes & fees
Sep 15 - Sep 16
Cameron Charmer pristine downtown apt with double master suites

3. Indigo Blue modern open vibe on tree lined street

Indigo Blue modern open vibe on tree lined street
Winchester Historic District
9.8 out of 10, Exceptional, (15 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 $304
CA $564 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 $188
CA $409 total
includes taxes & fees
Sep 21 - Sep 22
Stone chalet w/ views & hot tub

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 $188
CA $427 total
includes taxes & fees
Sep 15 - Sep 16
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 $227
CA $461 total
includes taxes & fees
Sep 20 - Sep 21
Forest 2BR chalet w/ hot tub & backyard

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 $258
CA $467 total
includes taxes & fees
Sep 30 - Oct 1
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

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!

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 14 - Sep 15
Luxury tiny home farm stay on historic property with hot tub in Stephens City

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 $325 total
includes taxes & fees
Sep 13 - Sep 14
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

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

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 $303 total
includes taxes & fees
Sep 6 - Sep 7
Quaint Mini Cottage in Shepherdstown - Walking Distance

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 $476 total
includes taxes & fees
Sep 9 - Sep 10
Cabin at the Gap | You Won't Believe the View!

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 $513 total
includes taxes & fees
Sep 7 - Sep 8
The Blue Jay | New House in the Woods w/ Hot Tub

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 $234
CA $506 total
includes taxes & fees
Sep 7 - Sep 8
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

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 $511 total
includes taxes & fees
Sep 10 - Sep 11
Blue Ridge Getaway - Sunset Views, A.T. Access

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!

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 $530 total
includes taxes & fees
Sep 14 - Sep 15
Cottage w/ Hot Tub and 100-Mile Valley Views!

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 $605 total
includes taxes & fees
Sep 21 - Sep 22
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

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 $152
CA $329 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

Find out more about Stephenson

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Stephenson. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.