Middleway Vacations from $325

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The Latest Middleway vacation packages

Price found within the past 48 hours. Click for updated prices.
Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $486, price is now $325 per person
$325
per person
Jun 18 - Jun 22
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
No reviews
Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
Save 100% on your flight
Price was $3,076, price is now $1,955 per person
$1,955
per person
Jun 16 - Jun 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (202 reviews)
My stay at the Rosewood Hotel was absolutely wonderful from start to finish. The level of service, attention to detail, and overall atmosphere made it a truly memorable experience. From the moment I arrived, the staff was warm, welcoming, and genuinely attentive. Check‑in was smooth and effortless, and I immediately felt like a valued guest. The room was beautifully designed—spacious, spotless, and thoughtfully arranged with luxurious touches throughout. The bed was incredibly comfortable, and the overall ambiance made it easy to relax. The hotel’s amenities were equally impressive. Whether enjoying the dining options, unwinding in the lounge areas, or simply taking in the elegant décor, everything felt refined and well-curated. Every interaction with the staff felt sincere, and the service consistently exceeded my expectations. Overall, my stay at the Rosewood was exceptional. I would highly recommend this hotel to anyone looking for comfort, luxury, and top‑tier hospitality. I’m already looking forward to returning!

Reviewed on Feb 19, 2026

Residence Inn Alexandria Old Town South at Carlyle

Residence Inn Alexandria Old Town South at Carlyle

3 out of 5
Eisenhower East
Save 100% on your flight
Price was $940, price is now $616 per person
$616
per person
Jun 16 - Jun 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,002 reviews)
Tip—park at lot next to Eisenhower metro station 8 daily vs 40 daily at hotel.5 min walk Place is close to metro and free dash buses

Reviewed on Apr 7, 2026

Placemakr Buzzard Point

Placemakr Buzzard Point

4 out of 5
Southwest
Save 100% on your flight
Price was $1,310, price is now $861 per person
$861
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (164 reviews)
The room was very nice and clean. It made me want to stay longer. Love the view especially floor to ceiling windows. Couldn’t have asked for better accommodations. We will be returning to this location.

Reviewed on Mar 30, 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $2,182, price is now $1,450 per person
$1,450
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,417 reviews)
We had a great weekend getaway at the Riggs. Would recommend. Clean and comfortable. High marks for staff.

Reviewed on Apr 11, 2026

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Discover the most popular places to visit in Middleway

A-T Gift Company Farm Winery

You can enjoy a tasting or tour at A-T Gift Company Farm Winery during your travels to Kearneysville. While you're in the area, find time to visit its casinos.

A-T Gift Company Farm Winery

Middleway Hotel Deals

Hampton Inn Martinsburg

Hampton Inn Martinsburg

2.5 out of 5
975 Foxcroft Ave Martinsburg WV
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $115 total per night from May 10 to May 11
$115 total
May 10 - May 11
Total with taxes and fees
8.8/10 Excellent! (1,019 reviews)
Breakfast and staff were wonderful! Parking and check in was easy. Only complaint, no vent in the bathroom, for ventilation during showering or using the bathroom.

Reviewed on Apr 12, 2026

Hampton Inn Martinsburg
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $138 total per night from Apr 19 to Apr 20
$138 total
Apr 19 - Apr 20
Total with taxes and fees
9.4/10 Exceptional! (1,009 reviews)
Great place in the middle of everything. Beautiful rooms.

Reviewed on Apr 11, 2026

The George Washington Hotel, A Wyndham Grand Hotel
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
Fully refundable
$91 nightly
The price is $99 total per night from Apr 19 to Apr 20
$99 total
Apr 19 - Apr 20
Total with taxes and fees
9/10 Wonderful! (1,005 reviews)
Place is very clean. Staff very friendly and helpful. Breakfast buffet was amazing!!! We will stay here again.

Reviewed on Apr 12, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 699 properties in Middleway
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.

Find the Best Middleway Vacation Packages

Middleway Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Hagerstown Regional Airport (HGR)

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Frequently asked questions

How much does a Middleway vacation package cost?
Offering great value package deals from $325 on Expedia, you'll be surprised at how little a vacation to Middleway costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Middleway?
You can generally find lower rates and better availability in November, December and January. Check out our cheap Middleway vacation packages and you could land some great off-season discounts.
How many days is enough for Middleway?
The ideal length for your Middleway vacation depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to check out all the leading attractions and discover some hidden treasures along the way.
How to find the best Middleway package deals?
Finding a cheap Middleway package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Middleway package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Middleway vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Middleway vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Middleway?
If you've got your Middleway travel dates confirmed, book as soon as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Middleway vacation packages?
Your Middleway getaway is meant to be an escape from your daily routine, not a source of money worries. So to allow you more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.