Middleway Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Middleway vacation rentals

Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (77 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
$127 nightly
The price is $141
Jun 29 - Jun 30
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Interior

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (37 reviews)
"Very welcoming, the house was way more than expected. My family and I didn't want to leave."
United States
Shanna B.
$323 nightly
The price is $359
Jun 8 - Jun 9
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
Terrace/patio

Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (62 reviews)
"Host was welcoming and place was as described and in very clean condition. "
United States
Junaid B.
$171 nightly
The price is $181
Jun 8 - Jun 9
Total with taxes and fees
Cozy Getaway near Harper`s Ferry, C&O & Potomac
Terrace/patio

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (37 reviews)
"Would come back anytime, very scenic and easy check-in process"
United States
Mark F.
$344 nightly
The price is $383
Jun 9 - Jun 10
Total with taxes and fees
Rebels Rest - Cabin with Enchanting Sunset Views!
TV, fireplace

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
9.8 out of 10, Exceptional, (67 reviews)
"Great home "
United States
January D.
$374 nightly
The price is $416
Jun 15 - Jun 16
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
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, (23 reviews)
"Great view, very secluded"
United States
Matt s.
$352 nightly
The price is $392
Jun 22 - Jun 23
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
Dining

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Harpers Ferry
10.0 out of 10, Exceptional, (90 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
$317 nightly
The price is $353
Jun 8 - Jun 9
Total with taxes and fees
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
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.
$302 nightly
The price is $326
Jun 28 - Jun 29
Total with taxes and fees
Forest chalet w/ hot tub & BBQ grill
Exterior

Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (24 reviews)
"The host was extremely welcoming and kind to us. We spent a week here and loved our stay. We are so grateful to have been able to stay here with Kim and Todd. "
United States
Christina H.
$189 nightly
The price is $200
Jun 7 - Jun 8
Total with taxes and fees
Beautiful, Historic, Hiking, Biking and C&O Canal
Interior

Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.8 out of 10, Exceptional, (12 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
$169 nightly
The price is $188
Jun 7 - Jun 8
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
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.
$309 nightly
The price is $344
Jun 8 - Jun 9
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
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, (69 reviews)
"Very quiet cabin. Nicely situated between Charles Town and Harper’s Ferry. "
United States
Kelly R.
$343 nightly
The price is $382
Jun 22 - Jun 23
Total with taxes and fees
Blue Ridge Getaway - Sunset Views, A.T. Access
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
$314 nightly
The price is $333
Jun 7 - Jun 8
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
Exterior

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.8 out of 10, Exceptional, (201 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
$166 nightly
The price is $176
Jun 7 - Jun 8
Total with taxes and fees
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
TV, fireplace

Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!
Harpers Ferry
9.8 out of 10, Exceptional, (9 reviews)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
$344 nightly
The price is $383
Jun 8 - Jun 9
Total with taxes and fees
Aslan's How - Cabin with Valley Views & Hot Tub!
Exterior

Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (6 reviews)
"Clean, great location, and charming/updated space. Highly recommend! Host was super communicative and helpful!! "
United States
Kaitlin L.
$236 nightly
The price is $250
Jun 7 - Jun 8
Total with taxes and fees
Historic Getaway near C&O Canal, hiking and biking
Exterior

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (23 reviews)
"The house had wonderful spaces to use for our weekend getaway!"
United States
Jessame P.
$331 nightly
The price is $369
Jun 15 - Jun 16
Total with taxes and fees
Lake View Retreat - Cottage Near a Peaceful Lake!
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, (38 reviews)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
$352 nightly
The price is $392
Jun 16 - Jun 17
Total with taxes and fees
Secluded Cabin a Stone's Throw From the A.T.!
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, (30 reviews)
"Wonderful communication with the host and we loved the hot tub surrounded by natural beauty "
United States
Lisa P.
$386 nightly
The price is $430
Jun 16 - Jun 17
Total with taxes and fees
The Oculus - Huge Cabin with a Hot Tub!
Property grounds

Cozy w/Fire Pit, Grill, Screened Porch & WiFi

Cozy w/Fire Pit, Grill, Screened Porch & WiFi
Harpers Ferry
10.0 out of 10, Exceptional, (3 reviews)
"The host was very communicative and the place was very clean. "
United States
Christopher M.
$284 nightly
The price is $305
Jun 8 - Jun 9
Total with taxes and fees
Cozy w/Fire Pit, Grill, Screened Porch & WiFi
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"The hotel was very clean and modern with a very minimalist vibe. I like that. No need for unnecessary extras. It was a great venue and we will be sure to stay again. Staff was very pleasant"
James 1-night trip
Posted 6 hours 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 $141 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?

Terra Alta - Incredible River Views and Hot Tub!: This vacation home rental near Middleway is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Clearbrook Park. 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.