Title: New Windsor Vacation Packages 2026 from $286 | Expedia.com

[New Windsor Travel Guide](https://expedia.com/New-Windsor.dx6122933)[Hotels in New Windsor](https://expedia.com/New-Windsor-Hotels.d6122933.Travel-Guide-Hotels)[Vacation Rentals in New Windsor](https://expedia.com/New-Windsor-Vacation-Rentals.d6122933.Travel-Guide-VacationRentals)[Flights to New Windsor](https://expedia.com/Cheap-Flights-To-New-Windsor.d6122933.Travel-Guide-Flights)[Car Rentals in New Windsor](https://expedia.com/Car-Rentals-In-New-Windsor.d6122933.Car-Rental-Guide)

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# New Windsor Vacations from $286

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to $1,045 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  
Plan, book, and manage your trip all in one place

## Your New Windsor Vacation

Food, history, entertainment and more … There's so much to discover with a New Windsor vacation package. And with the ability to customize your city getaway, it's guaranteed to be one you won't forget. Make sure to spend some time sightseeing during your trip to New Windsor. [Old Westminster Winery](https://www.expedia.com/Old-Westminster-Winery-New-Windsor.d553248621561182366.Vacation-Attraction) and [Elk Run Vineyards](https://www.expedia.com/Elk-Run-Vineyards-Mount-Airy.d6091699.Vacation-Attraction) are some favorite places to check out. Whoever you're escaping with and whatever your bank balance, your dream New Windsor vacation is just a few clicks away with Expedia.

## The Latest New Windsor vacation packages

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

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Historic Inns of Annapolis

Historic District

$286

per person

Jun 1 - Jun 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

9/10 Wonderful! (1,878 reviews)

Staff were a pleasure. Room was beautiful.

Reviewed on Mar 4, 2026

![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/89cd8abe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Baltimore

Fells Point

Save 100% on your flight

$2,260

per person

May 17 - May 23

found 1 hour ago

Roundtrip flight included

Minneapolis (MSP) to Baltimore (BWI)

9.4/10 Exceptional! (1,000 reviews)

Nice room, clean view of the water.

Reviewed on Feb 20, 2026

![Atlantic Sands Hotel & Conference Center](https://images.trvl-media.com/lodging/2000000/1160000/1151000/1150975/2aa1e794_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Atlantic Sands Hotel & Conference Center

North Rehoboth

$691

per person

Apr 17 - Apr 24

just found

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

8.4/10 Very Good! (1,401 reviews)

Yes very nice ocean view

Reviewed on Mar 3, 2026

![Unit 3 One BR With Queen  Sofa and  Bed ](https://images.trvl-media.com/lodging/119000000/118260000/118253300/118253252/9355c127_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Unit 3 One BR With Queen Sofa and Bed 

Downtown Washington D.C.

Save 100% on your flight

$765

per person

May 19 - May 24

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

9/10 Wonderful! (2 reviews)

![Homewood Suites by Hilton Arlington Rosslyn Key Bridge](https://images.trvl-media.com/lodging/20000000/19970000/19961800/19961795/f2657acd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Homewood Suites by Hilton Arlington Rosslyn Key Bridge

Rosslyn

Save 100% on your flight

$840

per person

May 19 - May 24

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

9.4/10 Exceptional! (1,000 reviews)

Handicapped room was large and had everything I needed. Bed was very comfortable. Breakfast was good

Reviewed on Mar 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to New Windsor

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-08/2026-04-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6122933)

### Discover the most popular places to visit in New Windsor

#### Old Westminster Winery

You can enjoy a tasting or tour at Old Westminster Winery during your travels to New Windsor. While in this family-friendly area, you can enjoy the restaurants. 

[](https://expedia.com/Old-Westminster-Winery-New-Windsor.d553248621561182366.Vacation-Attraction)

## New Windsor Hotel Deals

![Inn at Cemetery Hill](https://images.trvl-media.com/lodging/1000000/450000/447000/446925/074785e2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Inn at Cemetery Hill

613 Baltimore St Gettysburg PA

Fully refundableReserve now, pay when you stay

$88 nightly

$98 total

Mar 9 - Mar 10

Total with taxes and fees

9.4/10 Exceptional! (1,003 reviews)

Wrong time of the year to think about vinyards

Reviewed on Mar 5, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F9%2F2026&endDate=3%2F10%2F2026&selected=446925&PinnedHotelID=446925&HadPinnedHotel=true&regionId=6122933)

![Country Inn & Suites by Radisson, Frederick, MD](https://images.trvl-media.com/lodging/1000000/60000/59600/59588/1aff68d6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Country Inn & Suites by Radisson, Frederick, MD

5579 Spectrum Dr Frederick MD

Fully refundable

$84 nightly

$93 total

Mar 22 - Mar 23

Total with taxes and fees

8.4/10 Very Good! (1,270 reviews)

Clean room, friendly staff, nicely remodeled

Reviewed on Mar 6, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=59588&PinnedHotelID=59588&HadPinnedHotel=true&regionId=6122933)

![SpringHill Suites by Marriott Frederick](https://images.trvl-media.com/lodging/62000000/61640000/61631900/61631879/e35ce686_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

SpringHill Suites by Marriott Frederick

111 Byte Drive Frederick MD

Fully refundableReserve now, pay when you stay

$107 nightly

$119 total

Apr 1 - Apr 2

Total with taxes and fees

9.4/10 Exceptional! (769 reviews)

Great

Reviewed on Mar 3, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=61631879&PinnedHotelID=61631879&HadPinnedHotel=true&regionId=6122933)

[See all 348 properties in New Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F9%2F2026&endDate=3%2F10%2F2026&regionId=6122933)

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.

## Find the Best New Windsor Vacation Packages

## New Windsor Essential Information

| Language        | English     |
| --------------- | ----------- |
| Currency        | U.S dollars |
| Population      | 1,400       |
| Max Temp Winter | 40ºF        |
| Max Temp Summer | 80ºF        |

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## Frequently asked questions

### How much does a New Windsor vacation package cost?

### What are the cheapest months to go to New Windsor?

### How many days is enough for New Windsor?

### How to find the best New Windsor package deals?

### Is it cheaper to book a New Windsor vacation as a package?

### When to book a vacation package to New Windsor?

### Does Expedia offer Book Now, Pay Later New Windsor vacation packages?

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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