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Middleway Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Middleway vacation rentals

A house with a well-lit entrance, a small garden, and a gravel driveway.

1. 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 AED 314
AED 951 total
includes taxes & fees
5 Oct - 6 Oct
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

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

Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Martinsburg
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful location and property."
United States
Helen F.
The price is AED 533
AED 1,215 total
includes taxes & fees
30 Oct - 31 Oct
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Forest Haven is beautiful at night

3. 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 AED 605
AED 1,217 total
includes taxes & fees
5 Oct - 6 Oct
Forest 2BR chalet w/ hot tub & backyard
A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
8.0 out of 10, Very good, (23 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is AED 556
AED 1,281 total
includes taxes & fees
5 Oct - 6 Oct
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Grab a towel and relax in the hot tub

5. 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 AED 585
AED 1,263 total
includes taxes & fees
5 Oct - 6 Oct
Stone chalet w/ views & hot tub
A living room with a dining table, chairs, a sofa, and a television.

6. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"We loved staying here, and walking into town to.explore. The kitchen was well stocked, and the tub was.perfect for soaking after a long day hiking."
United States
Alexandra Z.
The price is AED 551
AED 945 total
includes taxes & fees
18 Oct - 19 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance
A spacious room with a large dining table, white chairs, and a ceiling fan.

7. ~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, (107 reviews)
"It was very clean, comfortable and well supplied with everything you would need. Beautiful scenery."
United States
John B.
The price is AED 614
AED 1,321 total
includes taxes & fees
6 Oct - 7 Oct
~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
A wooden deck with a table and chairs, a barbecue grill, and a red umbrella.

8. 3BR cabin w/ hot tub & game room

3BR cabin w/ hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (69 reviews)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
The price is AED 720
AED 1,320 total
includes taxes & fees
6 Oct - 7 Oct
3BR cabin w/ hot tub & game room
A forested area with a metal railing and a paved path.

9. Mountain Cabin in the Woods, Near Wineries & More!

Mountain Cabin in the Woods, Near Wineries & More!
Harpers Ferry
8.8 out of 10, Excellent, (35 reviews)
"House was cute with a great location! Very comfortable and host was very responsive!"
United States
Lisa P.
The price is AED 519
AED 905 total
includes taxes & fees
6 Oct - 7 Oct
Mountain Cabin in the Woods, Near Wineries & More!
A cylindrical metal building with a lit entrance, surrounded by trees.

10. Silo Tiny House Cabin

Silo Tiny House Cabin
Harpers Ferry
8.2 out of 10, Very good, (32 reviews)
"Cozy & Charming! Love the location! Really enjoyed our stay in the "Tiny House Silo!""
United States
Stephanie B.
The price is AED 680
AED 1,203 total
includes taxes & fees
5 Oct - 6 Oct
Silo Tiny House Cabin
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

11. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AED 966
AED 1,217 total
includes taxes & fees
13 Oct - 14 Oct
Schilling House
A covered outdoor area with wicker furniture, a ceiling fan, and a view of a lake and forest.

12. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"Clean house. Host was able to accessible. Hot tub worked and clean. Kitchen had everything we needed. Great place to stay and relax"
United States
Lisa h.
The price is AED 716
AED 1,984 total
includes taxes & fees
19 Oct - 20 Oct
Peaceful Lakefront Cottage with Mountain Views!
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

13. 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.
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A bedroom with a large bed, a bench, a chair, a nightstand, and a wall with decorative plates.

14. Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (21 reviews)
"Overall good property- close location to all attractions"
United States
Trisha P.
The price is AED 588
AED 1,530 total
includes taxes & fees
6 Oct - 7 Oct
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
A cozy living room with wooden walls, a flat-screen TV, a fireplace, and comfortable seating.

15. Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Harpers Ferry
9.2 out of 10, Wonderful, (52 reviews)
"Rental was exactly as advertised and in a great location within walking distance of a lot of great spots to check out."
United States
Sarah D.
The price is AED 533
AED 925 total
includes taxes & fees
11 Oct - 12 Oct
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
A modern building with a patio area, a fire pit, and a view of a river and forest.

16. 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.
Cabin at the Gap | You Won't Believe the View!
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, (21 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 AED 871
AED 2,156 total
includes taxes & fees
18 Oct - 19 Oct
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
A deck with outdoor seating and a lake view.

18. 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
10.0 out of 10, Exceptional, (11 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 AED 184
AED 945 total
includes taxes & fees
22 Oct - 23 Oct
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A wooden interior with a dining table set for four, a fireplace, and large windows offering a view of the outdoors.

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

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Harpers Ferry
9.8 out of 10, Exceptional, (49 reviews)
"Very relaxing great time."
United States
Alfred A.
The price is AED 646
AED 1,689 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
A covered deck with a table and chairs, overlooking a river and autumn foliage.

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

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (28 reviews)
"With bedrooms and sitting rooms on 3 floors, our 3-generation family enjoyed having space to gather together as well as space for time apart. The decks allowed for additional places to enjoy the beautiful surroundings. Lake access was great for swimming and kayaking."
United States
Lindy K.
The price is AED 500
AED 1,788 total
includes taxes & fees
7 Oct - 8 Oct
Art Docko - Lakefront Artist Retreat w/ 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 Middleway Hotel Reviews

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

8/10 Good
"It was a nice stay and the staff was very friendly. We will probably visit again."
Kira 1-night trip
Posted 6 hours ago
The Inn at Charles Town - Hollywood Casino

Frequently asked questions

Are there vacation rentals in Middleway?

Yes, we give you a choice of vacation rentals near top sights in Middleway, or you can choose a more remote option if you're looking for relaxation.

What's the top vacation rental that Middleway has to offer?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This vacation home rental near Middleway 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’s there to see and do in Middleway?

Explore the area and family-friendly sights such as Shenandoah Valley Discovery Museum, or get out into nature at a spot like Shenandoah Lake Beach. Locust Hill Golf Course and Summit Point Motorsports Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Middleway like?

Vacation rentals are private properties you can stay in for a long or short time in Middleway. Vacation rentals feature amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family trips or small group gatherings.