Windsor Vacations from $467

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Your Windsor Vacation

Our vacation packages to Windsor provide endless opportunities to delve into new sights, sounds and smells. And with all of the travel arrangements taken care of, you can kick back and enjoy your city escape to the fullest. Eager to do a little sightseeing? Spend your days enjoying popular attractions such as Franklin Pierce Homestead during your trip to Windsor. No matter your travel plans or budget, putting together a tailored Windsor vacation is easy with Expedia.

The Latest Windsor vacation packages

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

Exeter Inn

3.5 out of 5
Save 100% on your flight
Price was $743, price is now $467 per person
$467
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Manchester (MHT)
18/10 Exceptional! (1,000 reviews)
Friendly staff. Quaint room.

Reviewed on Nov 5, 2025

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
Price was $754, price is now $610 per person
$610
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Manchester (MHT)
18.8/10 Exceptional! (38 reviews)
Easy check-in, checkout; clean room; ready coffee machine! Quiet and cozy!

Reviewed on Nov 9, 2025

Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $1,138, price is now $963 per person
$963
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Springfield (VSF)
17.2/10 Exceptional! (539 reviews)
Small but clean room. Hotel is under construction but staff was accommodating and pleasant to work with durning our travel. If traveling for work we’d stay again

Reviewed on Nov 18, 2025

Chalet 239

Chalet 239

2 out of 5
Price was $989, price is now $854 per person
$854
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Springfield (VSF)
18.8/10 Exceptional! (87 reviews)
Absolutely the best value on the mountain! Loved the self service, breakfast and beautiful detail details

Reviewed on Oct 31, 2025

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Discover the most popular places to visit in Windsor

Eaton's Magic Morsel

Enjoy an outing to Eaton's Magic Morsel during your stay in Hillsboro. Discover the mountain views while you're in the area.

Eaton's Magic Morsel

Franklin Pierce Homestead

Learn about the local history of Hillsboro with a stop at Franklin Pierce Homestead. Discover the mountain views in this relaxing area.

Franklin Pierce Homestead

Windsor Hotel Deals

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
1403 New Hampshire Rte 103 Newbury NH
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $141 total per night from Dec 1 to Dec 2
$141 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (39 reviews)
Easy check in & out, room clean

Reviewed on Nov 10, 2025

Hideaway Inn Mt.Sunapee
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $99 total per night from Nov 20 to Nov 21
$99 total
Nov 20 - Nov 21
Total with taxes and fees
7/10 Good! (1,000 reviews)
Very professional people good service good staff

Reviewed on Nov 4, 2025

Days Inn by Wyndham Keene NH
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $151 total per night from Nov 20 to Nov 21
$151 total
Nov 20 - Nov 21
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
Easy check in and nice rooms

Reviewed on Nov 14, 2025

Best Western Plus Keene Hotel
See all 436 properties in Windsor
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 Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $467 on Expedia for your Windsor escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
You're likely to find lower prices and greater availability in October, November and December. Check out our cheap Windsor vacation packages and you could land some excellent off-season deals.
How many days is enough for Windsor?
The ideal length for your Windsor vacation depends on what you'd like to do. Typically, a handful of days to a week will give you time to visit all the leading sights and explore some hidden treasures along the way.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Windsor package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor escape underway.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still get the freedom to create a personalized Windsor vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Windsor?
Land incredible discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Windsor vacation.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Windsor trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.