Windsor Vacations from $903

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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.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $1,015, price is now $903 per person
$903
per person
Jun 14 - Jun 18
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

The Centennial

The Centennial

4 out of 5
Price was $1,344, price is now $969 per person
$969
per person
Jul 16 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
8.8/10 Excellent! (1,001 reviews)
Lovely and very helpful staff - Late night and early morning! Bed was very comfortable and breakfast was out early and very nice.

Reviewed on Apr 6, 2026

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was $1,819, price is now $1,524 per person
$1,524
per person
Jul 16 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
9.6/10 Exceptional! (366 reviews)
Very nice place, grounds are very well kept. Staff is very friendly & restaurants are excellent

Reviewed on May 4, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,075, price is now $904 per person
$904
per person
Jun 14 - Jun 18
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.8/10 Excellent! (923 reviews)
Lovely hotel with views of river and walkable to variety of shops and restaurants

Reviewed on May 12, 2026

Temple's Sunset Harbor

Temple's Sunset Harbor

4 out of 5
Save 100% on your flight
Price was $4,847, price is now $4,119 per person
$4,119
per person
Jun 14 - Jun 18
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Manchester (MHT)
No reviews
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Discover the most popular places to visit in Windsor

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

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

Windsor Hotel Deals

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
$154 nightly
The price is $167 total per night from May 17 to May 18
$167 total
May 17 - May 18
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
Room was very clean and people were very nice just thought full breakfast was more

Reviewed on May 15, 2026

Best Western Plus Keene Hotel
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
$105 nightly
The price is $113 total per night from May 31 to Jun 1
$113 total
May 31 - Jun 1
Total with taxes and fees
7/10 Good! (1,000 reviews)
The water was hot but the hotle is very very old. Everything needs an upgrade.

Reviewed on May 9, 2026

Days Inn by Wyndham Keene NH
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $152 total per night from May 26 to May 27
$152 total
May 26 - May 27
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
The hotel room was exceptionally clean and well maintained. The bed linens and bathroom were spotless, and the entire room smelled fresh upon arrival.

Reviewed on May 12, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
See all 469 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 $903 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.