Middleway Holidays from £805

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top Middleway Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Price was £1,208, price is now £805 per person
£805
per person
19 Sept - 26 Sept
found 2 hours ago
Return direct flight included
London (LON) to Baltimore (BWI)
9/10 Wonderful! (1,866 reviews)
The room was very dark. No outside window in our room.

Reviewed on 4 Jul 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 £2,982, price is now £1,784 per person
£1,784
per person
10 Sept - 17 Sept
found 23 hours ago
Return flight included
London (LHR) to Baltimore (BWI)
9.4/10 Exceptional! (1,196 reviews)
Great staff! Property clean and maintained (issues resolved quickly after told). NO breakfast included. Menu full and high priced meals. You can ask for a mini fridge for room.

Reviewed on 4 Jul 2026

The Melrose Georgetown Hotel

The Melrose Georgetown Hotel

4 out of 5
Northwest
Price was £1,319, price is now £922 per person
£922
per person
10 Sept - 17 Sept
found 23 hours ago
Return flight included
London (LHR) to Baltimore (BWI)
8.8/10 Excellent! (1,425 reviews)
They say they are 4 star but I’ve been to nicer 3 star hotel. The quality just wasn’t there, the front desk couldn’t even break a $100 for tip money. Room keys kept failing and security seem lacking but Georgetown is as safe as you get in DC.

Reviewed on 30 Jun 2026

The LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Northwest
Price was £1,275, price is now £894 per person
£894
per person
10 Sept - 17 Sept
found 23 hours ago
Return flight included
London (LHR) to Baltimore (BWI)
8.6/10 Excellent! (1,004 reviews)
Very cool place in a great part of town! Loved the staff:)

Reviewed on 30 Jun 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was £1,347, price is now £951 per person
£951
per person
13 Sept - 20 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Baltimore (BWI)
8.2/10 Very good! (1,005 reviews)
Awesome staff and such a variety of food! Place is so convenient!

Reviewed on 4 Jul 2026

Middleway Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Hagerstown Regional Airport (HGR)
Max Temp Winter
4ºC
Max Temp Summer
29ºC

Top hotels in Middleway

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
The price is £76 per night from 19 Jul to 20 Jul
£76
19 Jul - 20 Jul
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"Good location but floor was sticky in room and no closets, just open hooks."

Reviewed on 4 Jul 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
The price is £73 per night from 26 Jul to 27 Jul
£73
26 Jul - 27 Jul
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."

Reviewed on 28 Jun 2026

Spark by Hilton Winchester
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
The price is £111 per night from 28 Jul to 29 Jul
£111
28 Jul - 29 Jul
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"Very charming historic hotel. Close to very nice restaurants and tourist District."

Reviewed on 4 Jul 2026

The George Washington Hotel, A Wyndham Grand Hotel
See all 695 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Middleway travel package cost?
We make it simple for everyone to travel, with Middleway packages starting from just £805. You'll have the flexibility to bundle your favourite hotels, airlines and car rental. For the ultimate getaway, why not add some tours and experiences to your travel itinerary?
If I'm not able to travel, can I cancel my Middleway travel package?
Don't worry if you're rethinking your Middleway travel package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We totally understand life can sometimes throw you a curveball, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we're here to help.
How do I get a cheap travel package to Middleway?
Bundle your flights and hotels, add on extras such as a rental car or activities, and save with a Middleway travel package. You won't just enjoy awesome discounts on your escape — you'll have a world of choice within your reach too. When you book with Expedia, you can select from more than 550 air carriers and 1,000,000 hotels across the globe. Your unforgettable holiday starts right here, right now!
Does Expedia offer Book Now, Pay Later Middleway holidays?
Expedia has teamed up with online lender Klarna to make your next break easier on your wallet. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to pick from, so you're sure to find one that works with your budget. Check out these flexible payment options:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's manageable monthly instalment plans. If making bite-sized repayments each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: If you want to pay off your getaway in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

What are the top hotels in Middleway?
Get your trip off to a good start by locking in a room at Quality Inn & Suites. It's one of most sought-after hotels in Middleway. Another cosy option is Renovated Wv Schoolhouse: History Buff's Heaven.
How far in advance should I book my Middleway holiday?
Savvy travellers always book early. Air carriers generally advertise flight tickets around a year ahead of departure, and this is your chance to pick up some rock-bottom prices. Boss just told you to take some holiday time next month? That's fine too — Expedia are never short on fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Middleway travel package include?
Flights, rental cars and hotels, or any combination of them — the choice is yours. Whether you're venturing to Middleway with the entire family or travelling solo, there's a package to match every style and budget. Once you've made your booking, why not add on a few tours or activities?
What should I know before booking a Middleway travel package?
You can save big by combining your flights, hotels and rental cars. Once you've made your booking, you can add on things like activities or sightseeing tours. Your next awesome holiday is only a couple of clicks away.
Can I choose my airline with a Middleway Expedia travel package?
Yes, you can. We offer more than 550 airline partners around the world, so pick the carrier that best fits your travel preferences.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.