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Middleway Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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.
$233 nightly
The price is $259
Oct 21 - Oct 22
Total with taxes and fees
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.
$276 nightly
The price is $307
Nov 13 - Nov 14
Total with taxes and fees
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.
$305 nightly
The price is $340
Oct 22 - Oct 23
Total with taxes and fees
Forest 2BR chalet w/ hot tub & backyard
Grab a towel and relax in the hot tub

4. 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.
$359 nightly
The price is $389
Oct 19 - Oct 20
Total with taxes and fees
Stone chalet w/ views & hot tub
A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
7.8 out of 10, Good, (24 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
$299 nightly
The price is $323
Oct 18 - Oct 19
Total with taxes and fees
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
A living room with a TV, two sofas, a coffee table, and a large plant.

6. 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.
$363 nightly
The price is $393
Nov 2 - Nov 3
Total with taxes and fees
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
A covered outdoor area with wicker furniture, a ceiling fan, and a view of a lake and forest.

7. 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.
$416 nightly
The price is $463
Oct 20 - Oct 21
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
A deck with outdoor seating and a lake view.

8. 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, (12 reviews)
"We had a lovely stay and it was so nice for our dog as well. The Mountain Lake Cub had a doggy beach day on Saturday morning and it was a super fun experience. The host was friendly and responsive!"
United States
Dawn S.
$222 nightly
The price is $247
Oct 22 - Oct 23
Total with taxes and fees
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A wooden deck with a table and chairs, a barbecue grill, and a red umbrella.

9. 3BR cabin w/ hot tub & game room

3BR cabin w/ hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (70 reviews)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
$339 nightly
The price is $354
Oct 26 - Oct 27
Total with taxes and fees
3BR cabin w/ hot tub & game room
A spacious room with a large dining table, white chairs, and a ceiling fan.

10. 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, (108 reviews)
"It was very clean, comfortable and well supplied with everything you would need. Beautiful scenery."
United States
John B.
$352 nightly
The price is $392
Oct 29 - Oct 30
Total with taxes and fees
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake.
A living room with a dining table, chairs, a sofa, and a television.

11. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
$199 nightly
The price is $221
Oct 18 - Oct 19
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

12. 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, (4 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.
$232 nightly
The price is $263
Oct 19 - Oct 20
Total with taxes and fees
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.

13. 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.
$386 nightly
The price is $419
Oct 19 - Oct 20
Total with taxes and fees
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

14. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (87 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
$96 nightly
The price is $107
Oct 25 - Oct 26
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
A hot tub outside a building with a view of autumn trees.

15. 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, (29 reviews)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
United States
Rebecca N.
$308 nightly
The price is $343
Oct 21 - Oct 22
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

16. Schilling House

Schilling House
3.0 star property
Bolivar
$299 nightly
The price is $320
Oct 26 - Oct 27
Total with taxes and fees
Schilling House
A wooden deck with a table and chairs, a floating dock, and an umbrella providing shade.

17. Rustic Log Cabin with Private Dock on the Lake!

Rustic Log Cabin with Private Dock on the Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (15 reviews)
"Great location with beautiful views. Definitely would stay there again"
United States
David D.
$372 nightly
The price is $414
Oct 18 - Oct 19
Total with taxes and fees
Rustic Log Cabin with Private Dock on the Lake!
A modern building with a patio area, a fire pit, and a view of a river and forest.

18. 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.
$315 nightly
The price is $350
Nov 4 - Nov 5
Total with taxes and fees
Cabin at the Gap | You Won't Believe the View!
A forested area with a metal railing and a paved path.

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

Mountain Cabin in the Woods, Near Wineries & More!
Harpers Ferry
8.8 out of 10, Excellent, (36 reviews)
"House was cute with a great location! Very comfortable and host was very responsive!"
United States
Lisa P.
$223 nightly
The price is $248
Oct 19 - Oct 20
Total with taxes and fees
Mountain Cabin in the Woods, Near Wineries & More!
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

20. New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Bolivar
9.8 out of 10, Exceptional, (50 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
$261 nightly
The price is $291
Oct 18 - Oct 19
Total with taxes and fees
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"Staff was very friendly and helpful, rooms were clean and well kept, pool was nice, everything was convenient and comfortable"
Jessica 1-night trip
Posted less than an hour ago
TRU By Hilton Winchester

Find out more about Middleway

Everything you need to know about Middleway vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middleway vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middleway vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middleway vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middleway. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middleway in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $221 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middleway rentals

At Expedia, we put the best Middleway vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middleway rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middleway vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middleway. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.