Middleway Vacation Rentals

Dates

November 2026

December 2026

Check prices for these dates

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Our top choices for Middleway vacation rentals

A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

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

Martinsburg

Helen F.

$228 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

2. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Martinsburg

Arnold A.

$222 nightly

Nov 18 - Nov 19

Total with taxes and fees

A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

Shepherdstown

Dennis C.

$86 nightly

Nov 15 - Nov 16

Total with taxes and fees

A living room with a dining table, chairs, a sofa, and a television.

4. Quaint Mini Cottage in Shepherdstown - Walking Distance

Shepherdstown

Abigail

$184 nightly

Nov 15 - Nov 16

Total with taxes and fees

A forested area with a metal railing and a paved path.

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

Harpers Ferry

Jennifer H.

$234 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern building with a patio area, a fire pit, and a view of a river and forest.

6. Cabin at the Gap | You Won't Believe the View!

Harpers Ferry

Matthew P.

$307 nightly

Nov 10 - Nov 11

Total with taxes and fees

7. Forest 2BR chalet w/ hot tub & backyard

Gerrardstown

John Z.

$309 nightly

Nov 9 - Nov 10

Total with taxes and fees

A sunroom with a large glass wall, a dining table set for four, and a ceiling fan.

8. Log Cabin w/ Hot Tub & Waterfront Patio!

Harpers Ferry

Andrew A.

$372 nightly

Nov 11 - Nov 12

Total with taxes and fees

A covered outdoor area with wicker furniture, a ceiling fan, and a view of a lake and forest.

9. Peaceful Lakefront Cottage with Mountain Views!

Harpers Ferry

Tara G.

$384 nightly

Nov 18 - Nov 19

Total with taxes and fees

A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

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

Gerrardstown

Samantha N.

$302 nightly

Nov 15 - Nov 16

Total with taxes and fees

A room with a large window overlooking a forested area.

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

Harpers Ferry

Eliot W.

$368 nightly

Nov 12 - Nov 13

Total with taxes and fees

A hot tub with a view of a forested landscape during sunset.

12. Cottage w/ Hot Tub and 100-Mile Valley Views!

Harpers Ferry

Keri L.

$370 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern building with a stone facade and a balcony with red chairs.

13. Stone chalet w/ views & hot tub

Gerrardstown

Michael H.

$328 nightly

Nov 30 - Dec 1

Total with taxes and fees

A room with a large window, a round table, and two chairs.

14. Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

Harpers Ferry

Diane S.

$258 nightly

Dec 1 - Dec 2

Total with taxes and fees

A bedroom with a bed, two windows, a ceiling fan, a green armchair, a dresser, and a nightstand with a lamp.

15. Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

Gerrardstown

Amber H.

$312 nightly

Nov 16 - Nov 17

Total with taxes and fees

A covered deck with a table and chairs, overlooking a river and autumn foliage.

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

Harpers Ferry

Lindy K.

$434 nightly

Nov 18 - Nov 19

Total with taxes and fees

A hot tub outside a building with a view of autumn trees.

17. Woodsy Retreat with a Hot Tub and Seasonal Views!

Harpers Ferry

Rebecca N.

$354 nightly

Nov 19 - Nov 20

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

18. Walk to Stores: Home in Historic Shepherdstown!

Shepherdstown

$335 nightly

Nov 19 - Nov 20

Total with taxes and fees

A spacious living area with a fireplace, a sofa, and a coffee table.

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

Harpers Ferry

Tracy H.

$359 nightly

Nov 19 - Nov 20

Total with taxes and fees

A wooden interior with a dining table set for four, a fireplace, and large windows offering a view of the outdoors.

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

Harpers Ferry

Alfred A.

$398 nightly

Nov 19 - Nov 20

Total with taxes and fees

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Find vacation rentals that suit your style

Top Middleway Hotel Reviews

A refrigerated display case with various snacks and beverages, shelves with packaged goods, and a sign above indicating the section as 'Treats.'

Hampton Inn Martinsburg South-Inwood

Inwood

10/10 Excellent

Anonymous traveler

An outdoor patio area with wicker furniture, a stone fire feature, and a covered seating area with string lights.

Home2 Suites by Hilton Charles Town

Charles Town

10/10 Excellent

Tommy

A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.

Microtel Inn & Suites by Wyndham Winchester

Winchester

10/10 Excellent

Elizabeth

A traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.

Hillbrook Inn

Charles Town

10/10 Excellent

This is an Inn in a very rural area. It is very peaceful and this was much needed to quiet the mind. I went on the verge of the leaves changing in the fall so it was quite beautiful with changing leaves but still green grass and some plants blooming. I brought my small dog in this solo trip and it was a nice touch to leave a couple of milk bones in the room for him. I didn't go to the dining area for breakfast or dinner so I can't comment of this portion.

Patti

A swimming pool with a metal ladder, lounge chairs, and a seating area with a view of the outdoors.

Hampton Inn & Suites Charles Town

Charles Town

10/10 Excellent

Trisha

A bar area with high stools, a counter, and a patterned carpet.

Rodeway Inn & Suites Charles Town

Charles Town

10/10 Excellent

Julie

A self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.

TRU By Hilton Winchester

Winchester

10/10 Excellent

Eddy

A two-story house with a front porch, American flags, and a mailbox.

The Carriage Inn B&B

Charles Town

10/10 Excellent

retired teacher

A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.

Quality Inn Winchester

Winchester

10/10 Excellent

james

An outdoor patio with a fire feature, seating, and a covered area.

SpringHill Suites by Marriott Winchester

Winchester

10/10 Excellent

Lynette

A reception area with a blue door, a reception desk, and two armchairs.

Days Inn by Wyndham Charles Town/Harpers Ferry

Charles Town

10/10 Excellent

Wade

A modern hotel lobby with a central dining area, a reception desk, and a large window providing natural light.

Hampton Inn Winchester N/Conference Center, VA

Winchester

10/10 Excellent

Kevin

A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".

Spark by Hilton Winchester

Winchester

10/10 Excellent

Joan

A restaurant with a bar area, multiple tables and chairs, and a seating area with a sofa.

Holiday Inn Martinsburg by IHG

Martinsburg

10/10 Excellent

Nathan

A modern hotel lobby with seating areas, a reception desk, and a 'Welcome' sign.

Hampton Inn Martinsburg

Martinsburg

10/10 Excellent

Destiny

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 $96 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.