Old Town Winchester Holidays from NZ$2,725

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Top Holiday Package Deals in Old Town Winchester

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
per person
27 Sept - 29 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
8.2/10 Very Good! (1,005 reviews)
We encountered issues at check-in in but they could fix it relatively fast. The water did not get that hot, the carpet was dirty and the room was very dark even with all of the lights on. But the staff was excellent!

Reviewed on 11 Aug. 2025

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
per person
27 Sept - 29 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
9.4/10 Exceptional! (1,002 reviews)
Beautiful hotel in a great location!

Reviewed on 10 Aug. 2025

Sandaway Suites & Beach

Sandaway Suites & Beach

3 out of 5
per person
27 Sept - 29 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
9.4/10 Exceptional! (144 reviews)
Beautiful historic building and rooms. Scenic, quiet grounds, calming views of the bay. A true gem !

Reviewed on 3 Aug. 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
per person
27 Sept - 29 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
9/10 Wonderful! (1,824 reviews)
Charming area and loved to hotel decor!

Reviewed on 11 Aug. 2025

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

2.5 out of 5
per person
27 Sept - 29 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
9.6/10 Exceptional! (20 reviews)
Fantastic hotel with exceptional service and attention to detail. Debbie and the other members of staff were warm and welcoming, nothing was to much trouble. Look forward to staying there again in the future. Thank you for a wonderful stay.

Reviewed on 22 Jan. 2023

Our pick of the best Old Town Winchester Hotel Deals

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 NZ$241 per night from 18 Aug to 19 Aug
NZ$241
18 Aug - 19 Aug
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"This hotel is great. I’ve stayed there before and we’ll stay there again. My only gripe is that the hot tub wasn’t hot…it was warm, and there were no jets of any consequence… I absolutely recommend this hotel!"

Reviewed on 6 Aug. 2025

The George Washington Hotel, A Wyndham Grand Hotel
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
The price is NZ$190 per night from 1 Sept to 2 Sept
NZ$190
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,123 reviews)
"One of our fave places to stay when we visit Winchester."

Reviewed on 10 Aug. 2025

La Quinta Inn & Suites by Wyndham 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
The price is NZ$175 per night from 17 Aug to 18 Aug
NZ$175
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Wish breakfast was free. Other than that is was good."

Reviewed on 6 Aug. 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 355 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.

Frequently asked questions

How much does an Old Town Winchester holiday package cost?
Our Old Town Winchester holiday packages, which begin from just NZ$2,725, are the best way to save. All you have to do is choose your preferred hotels, flights and rental car to create your perfect getaway.
How do I get a cheap travel package to Old Town Winchester?
Our Old Town Winchester holiday packages offer plenty of savings for the savvy wanderer. For the best deal, simply bundle your hotel, flights and extras (including activities) into a handy package. But low prices are only the start of your next epic adventure. Book with Expedia and you'll have more than 550 air carriers and 1 000 000 hotels around the world to pick from. Whatever your budget or style, there's a package that's perfect for you.
Where should I stay in Old Town Winchester?
A holiday in Old Town Winchester wouldn't be complete without checking out Shenandoah University, Winchester Medical Centre and Museum of the Shenandoah Valley. Spend your evenings near these tourist attractions and make sightseeing a breeze.
What are the top hotels in Old Town Winchester?
Whether you plan to stay for a night or a week in Old Town Winchester, you'll get a wonderful night's rest at The George Washington Hotel, A Wyndham Grand Hotel. This option is a favourite with lots of travellers.
How far in advance should I book my Old Town Winchester holiday?
You'll be rewarded with the widest variety at the cheapest prices by booking your Old Town Winchester holiday nice and early. Airlines typically advertise tickets anywhere up to 12 months in advance, so start your planning as soon as possible. Having said that, Expedia is constantly working to give you the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Old Town Winchester travel package include?
Flights, hotels and car rentals — we connect you to all the best deals. All you'll have to do is decide on your favourite combination. Once you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to craft an amazing Old Town Winchester getaway.
What should I know before booking an Old Town Winchester travel package?
We already have low prices. However, you'll enjoy even more bargains when you book your flights, hotels and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a terrific range of choice.
Can I choose my airline with an Old Town Winchester Expedia holiday package?
With a holiday package, you're in charge. Whether you're looking to fly to Old Town Winchester in economy or business class, simply pick from the available airline options. Expedia has access to over 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Old Town Winchester holiday package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Booked your Old Town Winchester holiday package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a fee from your hotel, airline or car rental company. For further information, browse our Customer Service Portal. We're here to help you every step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.