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Middleway Holiday Rentals

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Our top choices for Middleway holiday rentals

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 NZ$457
includes taxes & fees
4 Oct - 5 Oct
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

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 NZ$595
includes taxes & fees
30 Oct - 31 Oct
Hidden Creekside retreat near 5 national parks, including Harpers Ferry

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 NZ$585
includes taxes & fees
12 Oct - 13 Oct
Forest 2BR chalet w/ hot tub & backyard

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 NZ$610
includes taxes & fees
4 Oct - 5 Oct
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

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 NZ$708
includes taxes & fees
2 Nov - 3 Nov
Stone chalet w/ views & hot tub

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 NZ$458
includes taxes & fees
18 Oct - 19 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance

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, (106 reviews)
"It was very clean, comfortable and well supplied with everything you would need. Beautiful scenery."
United States
John B.
The price is NZ$635
includes taxes & fees
6 Oct - 7 Oct
~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

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

3BR cabin w/ hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (68 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 NZ$647
includes taxes & fees
6 Oct - 7 Oct
3BR cabin w/ hot tub & game room

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 NZ$443
includes taxes & fees
5 Oct - 6 Oct
Mountain Cabin in the Woods, Near Wineries & More!

10. Wild And Wonderful Silos

Wild And Wonderful Silos
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 NZ$578
includes taxes & fees
5 Oct - 6 Oct
Wild And Wonderful Silos

11. Schilling House

Schilling House
3.0 star property
Bolivar
The price is NZ$554
includes taxes & fees
4 Oct - 5 Oct
Schilling House

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 NZ$949
includes taxes & fees
19 Oct - 20 Oct
Peaceful Lakefront Cottage with Mountain Views!

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.
The price is NZ$464
includes taxes & fees
4 Oct - 5 Oct
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

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 NZ$750
includes taxes & fees
6 Oct - 7 Oct
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

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, (51 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 NZ$414
includes taxes & fees
4 Oct - 5 Oct
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

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.
The price is NZ$678
includes taxes & fees
8 Oct - 9 Oct
Cabin at the Gap | You Won't Believe the View!

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

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 NZ$458
includes taxes & fees
22 Oct - 23 Oct
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

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 NZ$844
includes taxes & fees
13 Oct - 14 Oct
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

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 NZ$874
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

Find out more about Middleway

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middleway holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middleway. 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 Middleway. Seeing all the best attractions is bound to make you fall in love with Middleway. Who knows, you may even be tempted to extend your 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 holiday 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 Middleway short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Middleway?

Yes, there are holiday rentals close to the most popular sights in Middleway, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middleway has to offer?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This holiday home rental outside of Middleway is located in the mountains, and has a patio, a BBQ 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 wider area.

What’s a holiday rental in Middleway like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middleway. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.