Middleway Vacations from $341

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The Latest Middleway vacation packages

Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $563, price is now $341 per person
$341
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,005 reviews)
Being on a college campus did make arrival somewhat confusing. That was the end of any issues I had with this hotel. Staff was extremely helpful and courteous from jump. A problem I had in the room upon arrival was rectified immediately. Parking was a bit pricey, but worth it and close by. I most definitely will be chosing this location anytime I have to come to DC.

Reviewed on Jul 12, 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Save 100% on your flight
Price was $1,266, price is now $732 per person
$732
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,196 reviews)
We chose the hotel because it had a spa, which didnt disappoint and an outdoor pool. Overall hotel is very well maintained. Pool area a little small for the amount of guests, not enough lounge chairs..However Moises at the pool bar is a gem. Smiles easily, patient- considering ordering food can be challenging...he could use a food runner when its busy. Hotel ambience upscale and we felt safe. Our room was very nice and clean, Updated decor, spacious. Complimentary soap, shampoo etc were very, very nice. The view from our room not so nice as we mainly faced a brick wall, they should have discussed a possible upgrade$$?? Fortunately, we were only in the room for the most part to shower and sleep. Room was very quiet. The Restaurant wasvery busy and was challenged at breakfast time...seating and service experienced delays but the staff was always pleasant. Breakfast was pricey. Location on the Wharf was excellent. Would definitely stay again but would discuss room location and possible breakfast included price!

Reviewed on Jul 12, 2026

The Bethesdan Hotel, Tapestry Collection by Hilton

The Bethesdan Hotel, Tapestry Collection by Hilton

4 out of 5
Bethesda Downtown
Save 100% on your flight
Price was $557, price is now $346 per person
$346
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,881 reviews)
This was a very nice hotel for the price. It very easy to walk to the Metro station. Felt very safe. Hotel was very clean and the room was very nice! I would definitely go back!

Reviewed on Jul 13, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $916, price is now $571 per person
$571
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
8.8/10 Excellent! (1,005 reviews)
The property staff was awesome. Had a problem with TV and never fixed but staff did offer a change of rooms which I did not accept.

Reviewed on Jul 11, 2026

The LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Northwest
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Price was $756, price is now $480 per person
$480
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,006 reviews)
I would have given this a higher rating but felt assaulted when we entered the portico and into the hotel. The large pictures of seductive young men were offensive to us. The decor of the worn out carpet didn’t help. Then realizing it had been a church was insulting. The water pressure was difficult in our bathroom. The staff was wonderful and friendly. The rooms were clean.

Reviewed on Jul 12, 2026

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Middleway Hotel Deals

TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Jul 26 to Jul 27
$90 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (1,032 reviews)
"The room was very narrow. Only one person could pass tge bed at a time. There was no dressers to out clothes in. They only had hooks that you could hang up clothes. There was no closet in the room and no microwave. The only garbage pail was a small pail that was divided in half without a bag which ..."

Reviewed on Jul 13, 2026

TRU By Hilton Winchester
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $73 total per night from Jul 26 to Jul 27
$73 total
Jul 26 - Jul 27
Total with taxes and fees
9/10 Wonderful! (1,011 reviews)
"Great staff, clean rooms and delightful breakfast. I'll be back!"

Reviewed on Jul 5, 2026

Spark by Hilton Winchester
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
$86 nightly
The price is $95 total per night from Aug 2 to Aug 3
$95 total
Aug 2 - Aug 3
Total with taxes and fees
9.2/10 Wonderful! (1,017 reviews)
"Highly recommend. Good location and great amenities. Very clean."

Reviewed on Jul 12, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 706 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 $341 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.