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Stephenson Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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
8.8 out of 10, Excellent, (5 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 ￥23,319
￥39,095 total
includes taxes & fees
Nov 19 - Nov 20
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
7.8 out of 10, Good, (24 reviews)
"The price was reasonable and the house was clean. The owner communicated very well."
United States
Samantha N.
The price is ￥22,640
￥52,551 total
includes taxes & fees
Nov 8 - Nov 9
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

3. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (16 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is ￥30,724
￥52,483 total
includes taxes & fees
Nov 3 - Nov 4
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A two-story house with a front porch, a mailbox, and a number plate.

4. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.8 out of 10, Exceptional, (11 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 ￥31,197
￥52,841 total
includes taxes & fees
Nov 8 - Nov 9
Cameron Charmer pristine downtown apt with double master suites
A living room with a dining table, chairs, a sofa, and a television.

5. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (26 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
The price is ￥18,907
￥33,220 total
includes taxes & fees
Nov 8 - Nov 9
Quaint Mini Cottage in Shepherdstown - Walking Distance
A hot tub in front of a wooden cabin with a tree in the background.

6. 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, (15 reviews)
"This tiny house was an absolute dream to stay at! Jen is very attentive to detail- everything from the decor to the thoughtful welcome basket and supplying a feed bucket for the farm animals was perfection. My kids requested our next vacation just be there instead! "
United States
Laura H.
The price is ￥22,846
￥27,533 total
includes taxes & fees
Nov 16 - Nov 17
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A living room with a sofa, armchair, coffee table, and a television.

7. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
8.8 out of 10, Excellent, (21 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 ￥29,149
￥49,093 total
includes taxes & fees
Nov 5 - Nov 6
Nostalgia Lane in the heart of the city
A hot tub with a wooden deck, a wooden cabin with large windows, and a deck chair.

8. 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 ￥29,839
￥57,327 total
includes taxes & fees
Nov 30 - Dec 1
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Forest Haven is beautiful at night

9. 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 ￥26,990
￥53,819 total
includes taxes & fees
Nov 29 - Nov 30
Forest 2BR chalet w/ hot tub & backyard
A modern building with a stone facade and a balcony with red chairs.

10. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (44 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
The price is ￥28,640
￥57,930 total
includes taxes & fees
Nov 30 - Dec 1
Stone chalet w/ views & hot tub
A small wooden cabin with a porch, surrounded by trees.

11. Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV

Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
Berkeley Springs
10.0 out of 10, Exceptional, (3 reviews)
"Everything from booking the stay to arriving and checking in was quick and convenient. The host emailed us directions and was easy to navigate toThe owl was just the perfect size for "
United States
kayla c.
The price is ￥9,205
￥26,494 total
includes taxes & fees
Nov 3 - Nov 4
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
A modern building with a patio area, a fire pit, and a view of a river and forest.

12. 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 ￥16,701
￥56,924 total
includes taxes & fees
Nov 15 - Nov 16
Cabin at the Gap | You Won't Believe the View!
A room with a large window overlooking a forested area.

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

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
9.6 out of 10, Exceptional, (23 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 ￥15,756
￥63,705 total
includes taxes & fees
Nov 5 - Nov 6
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

14. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Martinsburg
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful location and property."
United States
Helen F.
The price is ￥19,144
￥44,120 total
includes taxes & fees
Nov 14 - Nov 15
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
A wooden deck with white railings and a covered porch area.

15. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (47 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is ￥21,271
￥33,671 total
includes taxes & fees
Nov 8 - Nov 9
Mountain View Bungalow in Front Royal
A hot tub in a forested area with a rocky ground and trees.

16. 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, (6 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 ￥15,756
￥61,667 total
includes taxes & fees
Nov 5 - Nov 6
The Blue Jay | New House in the Woods w/ Hot Tub
A hotel entrance with a sign, a wicker chair, a wooden lattice, and a white door.

17. Best location! The Pullman Apt @ historic 1799 Inn

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (62 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
The price is ￥21,381
￥34,418 total
includes taxes & fees
Nov 4 - Nov 5
Best location! The Pullman Apt @ historic 1799 Inn
A floor plan with a sunroom, deck, laundry area, and a chimney.

18. 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, (112 reviews)
"Communicative host, very clean, pictures as listed and pet friendly, great little touches throughout"
United States
24renders
The price is ￥20,483
￥47,448 total
includes taxes & fees
Dec 1 - Dec 2
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
A cozy cabin-style room with a bed, a couch, a wooden coffee table, a ceiling fan, and a television.

19. Fox Burrow @ Timber Ridge Retreat

Fox Burrow @ Timber Ridge Retreat
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥13,326
￥33,186 total
includes taxes & fees
Nov 3 - Nov 4
Fox Burrow @ Timber Ridge Retreat
A hot tub area with a wooden structure overhead, a bottle, and glasses.

20. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.4 out of 10, Exceptional, (40 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
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

Hillside Inn & Suite

Hillside Inn & Suite

8/10 Good
"The property appears to be older but they have been doing many updates. Fresh paint, flooring is new and the bathrooms recently remodeled. The bed was comfortable. Room was clean. Coffee and donuts in lobby for breakfast. Staff friendly. Safe and convenient location."
Timothy 1-night trip
Posted 2 hours ago
Hillside Inn & Suite

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?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: Visitors like this Stephenson vacation home rental. It is located in the mountains and has a patio, a barbecue grill, and air-conditioning to put you at ease 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 Jim Barnett Park. 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.