Middleway Vacations from $250

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The Latest Middleway vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $429, price is now $250 per person
$250
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8/10 Very Good! (1,015 reviews)
Though I was able to check in successfully and the hotel was clean and staff friendly enough. For whatever reason there were several additional attempts at charging my card. So I more than likely won’t stay here again

Reviewed on Sep 27, 2025

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
Save 100% on your flight
Price was $833, price is now $511 per person
$511
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,008 reviews)
Noisy - drilling construction work and banging on the wall behind the bed in the morning. Cold water ran hot for about 5 minutes. No coffee in room. Noisy ac. And we did not like having an interior room. But the room was clean and otherwise comfortable.

Reviewed on Sep 27, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
Price was $890, price is now $564 per person
$564
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8.8/10 Excellent! (1,011 reviews)
This hotel is very expensive so why charge $65 for my car.

Reviewed on Sep 28, 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
Price was $640, price is now $411 per person
$411
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,825 reviews)
The hotel location was perfect for a night out in town. Very walkable, room was comfortable and clean.

Reviewed on Sep 24, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
Price was $1,665, price is now $1,087 per person
$1,087
per person
Dec 14 - Dec 21
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.4/10 Exceptional! (1,004 reviews)
Service was excellent.

Reviewed on Sep 12, 2025

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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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $118 total per night from Oct 5 to Oct 6
$118 total
Oct 5 - Oct 6
Total with taxes and fees
9.2/10 Wonderful! (2,166 reviews)
"Friendly front desk..needed additional pillow and blanket ..got immediate response"

Reviewed on Sep 23, 2025

La Quinta Inn & Suites by Wyndham Winchester
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $99 total per night from Oct 5 to Oct 6
$99 total
Oct 5 - Oct 6
Total with taxes and fees
9/10 Wonderful! (1,012 reviews)
"Clean comfortable room. Friendly and attentive staff Two thumbs up!"

Reviewed on Sep 25, 2025

Hampton Inn Winchester-University/Mall Area
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $91 total per night from Oct 26 to Oct 27
$91 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (1,346 reviews)
"Very nice place to stay. Everything is perfectly placed and the amenities were good."

Reviewed on Sep 21, 2025

Microtel Inn & Suites by Wyndham Winchester
See all 665 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.

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Frequently asked questions

How much does a Middleway vacation package cost?
Offering great value package deals from $250 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.