Old Town Winchester Holidays from £1,356

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

Your Old Town Winchester Holiday

Book a customized holiday package to Old Town Winchester and experience the charms of this neighbourhood from dawn to dusk. From its cafes and history to its unique personality and vibe, there are tons of fabulous reasons to visit Old Town Winchester. Can't wait to get out and see the sights during your trip to Old Town Winchester? Pencil in a visit to nearby attractions such as Shenandoah University, Rock Harbour Golf Course and Museum of the Shenandoah Valley. Stop daydreaming and start doing. When you're ready to lock in your holiday to Old Town Winchester, Expedia will help get you there.

Price found within the past 48 hours. Click for updated prices.
Sonesta Hotel Baltimore Inner Harbor

Sonesta Hotel Baltimore Inner Harbor

4 out of 5
Downtown Baltimore
Price was £1,438, price is now £1,356 per person
£1,356
per person
28 Jun - 4 Jul
found 1 day ago
Return flight included
London (LHR) to Baltimore (BWI)
8.2/10 Very Good! (1,389 reviews)
Room was great but the shower disappointed. There was no hot water and the shower head was broken.

Reviewed on 14 May 2026

Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Price was £2,310, price is now £2,089 per person
£2,089
per person
28 Jun - 4 Jul
found 1 day ago
Return flight included
London (LHR) to Baltimore (BWI)
9.4/10 Exceptional! (1,000 reviews)
My friend and I stayed here as a weekend getaway. It was absolutely perfect. The service was phenomenal from start to finish. We did have an issue with valet but they corrected it immediately and gave us a discount on the cost. The hotel is stunning, lives up to all the hype.

Reviewed on 4 May 2026

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was £1,492, price is now £1,359 per person
£1,359
per person
28 Jun - 4 Jul
found 1 day ago
Return flight included
London (LHR) to Baltimore (BWI)
8.4/10 Very Good! (1,001 reviews)
It’s very clean and in great area close to the shopping mall

Reviewed on 13 May 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was £1,495, price is now £1,399 per person
£1,399
per person
28 Jun - 4 Jul
found 1 day ago
Return flight included
London (LHR) to Baltimore (BWI)
8.4/10 Very Good! (2,712 reviews)
Great place, wonderful location, and always a good stay!

Reviewed on 14 May 2026

Baltimore Marriott Inner Harbor at Camden Yards

Baltimore Marriott Inner Harbor at Camden Yards

4 out of 5
Downtown West
Price was £1,593, price is now £1,501 per person
£1,501
per person
28 Jun - 4 Jul
found 18 hours ago
Return flight included
London (LHR) to Baltimore (BWI)
8.2/10 Very Good! (1,036 reviews)
Clean room, staff was great, restaurants were fun! Remodeling is taking place so some signs of construction. No noise that we noticed, just signs of a hopefully siccessful remodel. Stay here every time we come to Orioles games.

Reviewed on 27 Apr 2026

Top hotels in Old Town 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 £103 per night from 11 Jun to 12 Jun
£103
11 Jun - 12 Jun
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
The staff was helpful and kind. The architecture was incredible.

Reviewed on 12 May 2026

The George Washington Hotel, A Wyndham Grand Hotel
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 £72 per night from 31 May to 1 Jun
£72
31 May - 1 Jun
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
Could have had more of a selection for breakfast. Christine welcomed me with a smile & welcome. Makes you feel good right off the bat!

Reviewed on 15 May 2026

Spark by Hilton Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is £58 per night from 17 May to 18 May
£58
17 May - 18 May
includes taxes & fees
8.6/10 Excellent! (1,069 reviews)
Location was convenient. Staff were freindly and helpful.

Reviewed on 15 May 2026

Travelodge by Wyndham Winchester
See all 370 properties in Old Town Winchester
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 an Old Town Winchester travel package cost?
Maybe less than you imagined — from a low £1,356, as a matter of fact! By combining flights, hotels and car rentals into a tailor-made travel package, your trip to Old Town Winchester is just a few clicks away.
If I'm not able to travel, can I cancel my Old Town Winchester travel package?
It's hard to predict what the future holds, so it's comforting to know that you can change or cancel your Old Town Winchester travel package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Old Town Winchester?
If you love getting an amazing deal, bundle your bookings into an Old Town Winchester travel package. Whether you need flights, hotels, activities or rental cars, you can browse and book them all in one place. You'll have a wealth of choice at your fingertips too. Expedia has over 550 airlines and 1,000,000 properties all over the world to choose from. Fly with who you prefer, find a room where you like and save a tidy sum — now that's the perfect escape!
Does Expedia offer Book Now, Pay Later Old Town Winchester holidays?
Expedia has joined forces with online lender Klarna to make your next trip easier on your wallet. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more money to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that suits your budget. Consider these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month works for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

Where should I stay in Old Town Winchester?
With interesting attractions like Winchester Medical Centre and Shenandoah University in this area, look for a hotel located near them. Apple Blossom Mall is another sight that pulls the crowds.
What are the top hotels in Old Town Winchester?
If this will be your first visit to Old Town Winchester, lock in a room at Travelodge by Wyndham Winchester or Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel. Both hotels have good amenities and are popular options with many travellers.
How far in advance should I book my Old Town Winchester holiday?
It depends on the airline, but it's usually possible to browse through international fares on Expedia up to 12 months in advance. While it's generally recommended to book ahead of time, lucky travellers occasionally nab a cheaper ticket only weeks before the date of departure.
What does an Expedia Old Town Winchester travel package include?
With Expedia, you can choose a combination of hotels, car rentals and flights to create your ideal Old Town Winchester travel package. Once you've made your booking, you can add on the fun stuff like tours and activities. Remember — the more you bundle, the more dollars you'll save!
What should I know before booking an Old Town Winchester travel package?
When you book your flights, hotels and car rentals together, you'll score terrific discounts. Whether you're planning a rural escape in a cottage or want to stay in a luxurious city hotel, Expedia will help make it happen.
Can I choose my airline with an Old Town Winchester Expedia travel package?
Definitely. Expedia has more than 550 partner airlines to choose from across the world. With such a huge range of choice, finding the right carrier to whisk you away to Old Town Winchester shouldn't be hard.

Popular places to visit

Shenandoah Valley Discovery Museum

4/5(1 review)

You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Shenandoah Valley Discovery Museum

Bright Box Theater

Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Bright Box Theater

Apple Blossom Mall

You can search for that perfect souvenir at Apple Blossom Mall during your stay in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Apple Blossom Mall

* 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.