Winchester Holidays

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Your Winchester Holiday

Book a Winchester holiday package and discover the atmosphere and rhythm of this sought-after neighbourhood. With all your travel plans worked out, the only thing you need to concentrate on here is having an absolute ball. Some leading nearby attractions to check out during your trip to Winchester include Oriole Park at Camden Yards, M&T Bank Stadium and Baltimore Museum of Art. Whatever your ideal Winchester holiday looks like, you can turn it into reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
  • View from property
    Jul 2 - Jul 16

    Residence Inn by Marriott Alexandria Old Town South at Carlyle + Flight

    Eisenhower East
    14 nights
    3.0 star property
    8.8/10 - Excellent (1,003 reviews)
    "We come to Alexandria every month for two weeks. There are many restaurants and supermarkets in the area. Metro is just minutes away and location is right on the bus line. Love that there is a kitchen in the rooms with a full fridge. We do a lot of cooking! Hotel is just a quarter of a mile from a great dog park and our little dog loves going there. Staff is friendly and helpful. There is a small outside seating area, and it is a relaxing place after a day out. Sat out there most of the..."
    Reviewed May 30, 2026
    Return • Sydney (SYD) - Baltimore (BWI)
    SYD - BWI • 1 stop DCA - SYD • 1 stop
    AU$5,823
    AU$4,690
    per traveller
    found 1 day ago
    Residence Inn by Marriott Alexandria Old Town South at Carlyle
  • Rooftop terrace
    Jul 2 - Jul 16

    Landing at Bridge District + Flight

    Southeast
    14 nights
    4.0 star property
    8.6/10 - Excellent (34 reviews)
    "Loved staying there. People were friendly and welcoming. Building is new and the apartment super clean and comfortable"
    Reviewed May 27, 2026
    Return • Sydney (SYD) - Baltimore (BWI)
    SYD - BWI • 1 stop DCA - SYD • 1 stop
    AU$7,387
    AU$5,241
    per traveller
    found 1 day ago
    Landing at Bridge District
  • Exterior
    Jul 2 - Jul 16

    Eurostars Saint Gregory Dupont Circle Georgetown + Flight

    Downtown Washington D.C.
    14 nights
    4.0 star property
    8.8/10 - Excellent (1,000 reviews)
    "Unexpected upgrade at check in. Was much appreciated!"
    Reviewed May 16, 2026
    Return • Sydney (SYD) - Baltimore (BWI)
    SYD - BWI • 1 stop DCA - SYD • 1 stop
    AU$7,928
    AU$5,777
    per traveller
    found 1 day ago
    Eurostars Saint Gregory Dupont Circle Georgetown
  • Terrace/patio
    Jul 2 - Jul 16

    Kellogg Conference Hotel at Gallaudet University + Flight

    Northeast
    14 nights
    3.0 star property
    8.2/10 - Very good (1,004 reviews)
    "This could have easily been a rough stay, but the staff was very accommodating and kind. Thanks to everyone, especially Twanda."
    Reviewed May 25, 2026
    Return • Sydney (SYD) - Baltimore (BWI)
    SYD - BWI • 1 stop DCA - SYD • 1 stop
    AU$7,315
    AU$5,459
    per traveller
    found 1 day ago
    Kellogg Conference Hotel at Gallaudet University
  • Lobby
    Jul 2 - Jul 16

    Hilton Arlington National Landing + Flight

    Crystal City
    14 nights
    4.0 star property
    8.8/10 - Excellent (826 reviews)
    "We only got a Room for One Night, as we had an Early Morning Departure. It was on the 1st Floor, and a few Doors down was a Conference Room, that was being used for a Conference. The Bathroom Bathtub/Shower did NOT drain. It was 8pm at night and we weren’t staying up late for Maintenance. My Husband was able to take the Drain Stopper out, and it was CLOGGED with so much Hair, and the Drain Pipe was STILL draining extremely slow. The Bathroom Cold Water Handle did NOT work. The Restaurant for..."
    Reviewed May 26, 2026
    Return • Sydney (SYD) - Baltimore (BWI)
    SYD - BWI • 1 stop DCA - SYD • 1 stop
    AU$7,446
    AU$5,980
    per traveller
    found 1 day ago
    Hilton Arlington National Landing

Our guide on where to stay in Winchester

Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester
Inner Harbor

Inner Harbor

2 out of top 10 points of interest in this area

The captivating waterfront views and popular shops are just a few highlights of Inner Harbor. Make a stop by Baltimore Inner Harbor Marina or Harborplace while you're exploring the area.

Find hotels in Inner Harbor

Our pick of the best Winchester Hotel Deals

Sonesta Hotel Baltimore Inner Harbor

Sonesta Hotel Baltimore Inner Harbor

4 out of 5
1 East Redwood Street Baltimore MD
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 4 June to 5 June
AU$182
4 June - 5 June
includes taxes & fees
8.2/10 Very Good! (1,493 reviews)
"Everyone was very helpful. Check-in and check-out processes were easy and quick. The room was clean, and I liked the location. They have a restaurant, but I didn’t eat there. I’ll stay here again when I come back!"

Reviewed on 31 May 2026

Sonesta Hotel Baltimore Inner Harbor
Sonesta ES Suites Baltimore BWI Airport

Sonesta ES Suites Baltimore BWI Airport

3 out of 5
1160 Winterson Rd Linthicum Heights MD
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 9 June to 10 June
AU$181
9 June - 10 June
includes taxes & fees
8/10 Very Good! (1,284 reviews)
"My room was decent... nice room... the temperature dropped one night and i turned on the heat which lifted the smell of cat urine from the carpet. I called the front desk and they brought up a plug-in deoderizer to suppress the oder. It did by about 80%."

Reviewed on 31 May 2026

Sonesta ES Suites Baltimore BWI Airport
Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

3 out of 5
815 Elkridge Landing Road Linthicum Heights MD
Fully refundable
The price is AU$187 per night from 7 June to 8 June
AU$187
7 June - 8 June
includes taxes & fees
9.2/10 Wonderful! (1,246 reviews)
"Great staff"

Reviewed on 31 May 2026

Holiday Inn Baltimore BWI Airport by IHG
See all 1,415 properties in 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.
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Frequently asked questions

How much does a Winchester holiday package cost?
Custom build your Winchester holiday package from as little as . Pick from any combination of flights, hotels and rental cars to put together the escape you've been dreaming of. Don't forget to add on one or two experiences!
How do I get a cheap travel package to Winchester?
Browse and lock in everything in one place with our Winchester holiday packages. We have incredible bargains on flights, hotels and more that'll keep your credit card happy and your adventurousness alive. And, with more than 550 partner airlines and 1 000 000 hotel options all over the world to choose from, you'll have endless opportunities to mix and match your own way.
Where should I stay in Winchester?
A trip to Winchester isn't complete without stopping by National Aquarium in Baltimore and Oriole Park at Camden Yards. Stay at a hotel within walking distance for quick access to these fantastic attractions.
How far in advance should I book my Winchester holiday?
Reserving your flights early with Expedia means one less thing to have to worry about. Most carriers advertise tickets up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, discount prices to Winchester sometimes occur a few weeks before departure.
What does an Expedia Winchester travel package include?
Packages include flights, rental cars and hotels, but you can mix and match them to create your dream Winchester holiday. You can also add on tours and activities once you've made your booking. You're in the driver's seat! When you bundle your bookings with Expedia, you'll score deals you won't find elsewhere.
Can I choose my airline with a Winchester Expedia holiday package?
Yes, you sure can. We have more than 550 airline partners across the globe, so go with the carrier that's a good fit for your budget and travel needs.
If I'm not able to travel, can I cancel my Winchester holiday package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Winchester holiday package. If you made your booking in the last 24 hours, you may be entitled to a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal to learn more.

Discover the most popular places to visit in Winchester

Oriole Park at Camden Yards

Oriole Park at Camden Yards

4.5/5(3 reviews)

Watch Baltimore’s beloved baseball team play on their home field, located inside a groundbreaking stadium famous for blending classic and modern design elements.

Oriole Park at Camden Yards
M&T Bank Stadium

M&T Bank Stadium

4/5(1 review)

Catch an event at M&T Bank Stadium during your trip to Baltimore. Amble around this vibrant area's waterfront or experience its lively festivals.

M&T Bank Stadium
Johns Hopkins University

Johns Hopkins University

4/5(2 reviews)

Enjoy the student vibe with a visit to Johns Hopkins University, a well-known university in Baltimore. Amble around this vibrant area's waterfront or attend a sporting event.

Johns Hopkins University

Activities

Grand entrance to the Hard Rock Cafe in Baltimore

Dining at Hard Rock Cafe Baltimore

AU$56
per traveller
Dining at Hard Rock Cafe Baltimore
Downtown Baltimore History and Culture Self-Guided Audio Tour

Downtown Baltimore History and Culture Self-Guided Audio Tour

AU$15
per traveller
Downtown Baltimore History and Culture Self-Guided Audio Tour
Historical Baltimore Self-Driving Sightseeing Audio Tour

Historical Baltimore Self-Guided Driving & Walking Audio Tour

AU$21
per traveller
Historical Baltimore Self-Guided Driving & Walking Audio Tour
See all activities in Baltimore
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.