Default HTG hotel image

Middleway Vacation Rentals

Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Middleway vacation rentals

Exterior

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)
"Host was super nice and location was pretty. "
United States
Kimberly B.
$243 nightly
The price is $270
Jul 26 - Jul 27
Total with taxes and fees
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (80 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
$120 nightly
The price is $133
Aug 3 - Aug 4
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Smart TV, fireplace

Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (73 reviews)
"We had a wonderful stay. Fantastic views from this cabin -- literally on top of the mountain. Hot tub was great, love the rocking chairs on the front porch, and really appreciate the games and "activites" in the house (like the basetball game in the basement). It was easy to bring our teenage boys and enjoy some down time for spring break. I'm sure the roads would be dicey in the winter but loved it and would definately stay there again."
United States
Jill R.
$341 nightly
The price is $380
Aug 5 - Aug 6
Total with taxes and fees
Blue Ridge Getaway - Sunset Views, A.T. Access
Dining

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, (94 reviews)
"This is a beautiful, clean, traquil and relaxing home away from home. The beds are comfortable, the living space is open and full of light during the day. The hosts have made great efforts to make this a family and/or couple friendly destination. Our dog was welcomed and enjoyed her stay (being with her people). The views are spectacular."
United States
Deb K.
$318 nightly
The price is $354
Jul 30 - Jul 31
Total with taxes and fees
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Outdoor spa tub

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, (4 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.
$328 nightly
The price is $365
Jul 27 - Jul 28
Total with taxes and fees
The Blue Jay | New House in the Woods w/ Hot Tub
Smart TV

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, (18 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.
$351 nightly
The price is $391
Jul 29 - Jul 30
Total with taxes and fees
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Dining

The Oculus - Huge Cabin with a Hot Tub!

The Oculus - Huge Cabin with a Hot Tub!
Harpers Ferry
9.6 out of 10, Exceptional, (32 reviews)
"We had a lovely weekend staying at Mountain Momma! The rooms were clean and the kitchen was great for cooking for a large group. "
United States
Mary C.
$390 nightly
The price is $434
Jul 29 - Jul 30
Total with taxes and fees
The Oculus - Huge Cabin with a Hot Tub!
Smart TV, fireplace

Secluded Cabin a Stone's Throw From the A.T.!

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (40 reviews)
"Great cozy cabin to getaway to! Plenty of room for 6 of us to relax. Beds were comfortable, well-stocked kitchen, and hot tub was a nice perk. Will keep in mind if we come back to the area!"
United States
Cara M.
$336 nightly
The price is $375
Jul 23 - Jul 24
Total with taxes and fees
Secluded Cabin a Stone's Throw From the A.T.!
Terrace/patio

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.
$306 nightly
The price is $341
Jul 23 - Jul 24
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
Outdoor spa tub

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.
$312 nightly
The price is $336
Aug 10 - Aug 11
Total with taxes and fees
Stone chalet w/ views & hot tub
Terrace/patio

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.
$273 nightly
The price is $294
Jul 28 - Jul 29
Total with taxes and fees
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Interior

Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill
Harpers Ferry
9.2 out of 10, Wonderful, (33 reviews)
"Very nice cabin. Close to Harpers Ferry. Comfortable"
United States
Dianne A.
$354 nightly
The price is $383
Jul 29 - Jul 30
Total with taxes and fees
Forest chalet w/ hot tub & BBQ grill
Terrace/patio

Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveler
$155 nightly
The price is $176
Jul 22 - Jul 23
Total with taxes and fees
Cozy English Basement Apt quiet but close to downtown
TV, fireplace, offices

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
8.0 out of 10, Very Good, (17 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
$288 nightly
The price is $311
Jul 28 - Jul 29
Total with taxes and fees
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Outdoor dining

3BR cabin w/ hot tub & game room

3BR cabin w/ hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"While there was something left to be desired by the kitchen utensils and cookware, this place is located off the beaten path in a beautiful mountainside area. Definitely worth the price. Just bring your own pot holders and pizza cutter if you plan on having pizza lol. "
United States
Tyrell O.
$312 nightly
The price is $326
Jul 22 - Jul 23
Total with taxes and fees
3BR cabin w/ hot tub & game room
3 bedrooms, desk, iron/ironing board, travel crib

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, (13 reviews)
"Nice modern place with great amenities. Fenced yard was great for the pooches."
United States
John M.
$359 nightly
The price is $390
Jul 22 - Jul 23
Total with taxes and fees
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Outdoor spa tub

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)
"This was a lovely rental in a breathtaking location. My whole family gasped at that view as we came over the hill and down the driveway! Could not have asked for a more picturesque front yard, and the sunsets from the hot tub were epic. The house was very clean, comfortable, and well appointed, with two generously sized bath tubs inside and comfy beds. Great game selection (although some of the contents were mixed into the wrong boxes), and we enjoyed the ping pong table too. Communication...
United States
Lauren P.
$381 nightly
The price is $424
Jul 28 - Jul 29
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
Exterior detail

Silo Tiny House Cabin

Silo Tiny House Cabin
Harpers Ferry
8.2 out of 10, Very Good, (25 reviews)
"The silo was cute. A little small for our liking, but it was a place to rest our heads. The location was excellent and fairly close to hiking, biking trails, as well as the towns near by."
United States
Kelli M.
$266 nightly
The price is $296
Jul 23 - Jul 24
Total with taxes and fees
Silo Tiny House Cabin
Smart TV, fireplace, DVD player, books

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (109 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
$368 nightly
The price is $410
Aug 2 - Aug 3
Total with taxes and fees
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds

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, (14 reviews)
"Great location with beautiful views. Definitely would stay there again"
United States
David D.
$369 nightly
The price is $411
Jul 23 - Jul 24
Total with taxes and fees
Rustic Log Cabin with Private Dock on the Lake!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middleway Hotel Reviews

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

8/10 Good
"Rooms were large and clean. Maid service everyday which is a nice change from the Marriott brand which is upon request. Check in was a little slow, restaurant had nice service and good food but had some issues with their POS system and beer taps. Overall a wonderful place to stay at an affordable cost."
Randy 3-night trip
Posted 2 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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 $133 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?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This vacation home rental near Middleway offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Middleway?

Explore the area and family-friendly sights such as For the Kids, By George Children's Museum, or get out into nature at a spot like Mackintosh Fruit Farm. Summit Point Motorsports Park and Old Opera House 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.