Windsor Vacations from $482

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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.
Moultonborough Inn

Moultonborough Inn

3 out of 5
Price was $637, price is now $482 per person
$482
per person
Oct 1 - Oct 4
found 23 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Manchester (MHT)
9/10 Wonderful! (215 reviews)
No problems everything went well

Reviewed on Jun 29, 2026

Exeter Inn

Exeter Inn

3.5 out of 5
Price was $723, price is now $517 per person
$517
per person
Oct 1 - Oct 4
found 23 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Manchester (MHT)
9/10 Wonderful! (1,001 reviews)
Beautiful property with a great staff right next to the Phillips Exeter Academy. Perfect stay in Exeter.

Reviewed on Jul 7, 2026

The Centennial

The Centennial

4 out of 5
Save 100% on your flight
Price was $1,217, price is now $872 per person
$872
per person
Oct 1 - Oct 5
found 2 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
8.8/10 Excellent! (1,000 reviews)
The room was clean and comfortable but there was a window ac unit and no shade on the window. Closing the curtains for privacy meant blocking the ac. The room also lacked a full length mirror and had limited bathroom vanity space. I did like the laminate floors, the room was a nice size and the bed was comfy

Reviewed on Jul 5, 2026

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Price was $756, price is now $548 per person
$548
per person
Oct 1 - Oct 4
found 23 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Manchester (MHT)
9.2/10 Wonderful! (224 reviews)
Location is good, value is fair. Furniture old and start being cranky.

Reviewed on Jul 4, 2026

The Lake Estate on Winnisquam

The Lake Estate on Winnisquam

4.5 out of 5
Save 100% on your flight
Price was $1,703, price is now $1,245 per person
$1,245
per person
Oct 1 - Oct 5
found 2 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
9.8/10 Exceptional! (41 reviews)
Beautiful property, very good food, amenities and staff and convenient for area attractions (easy 20 minute ride to Weirs Beach). Our new favorite.

Reviewed on Jul 8, 2026

Don't see what you're looking for?
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Stay near popular Windsor attractions

Windsor Town Hall

Windsor Town Hall is just one of the places to see in Windsor, so why not enjoy the other things to explore during your travels?
See properties

Windsor Hotel Deals

Lakefront Cabin in Beautiful, Quiet Location

Lakefront Cabin in Beautiful, Quiet Location

Windsor NH
Get rates
Lakefront Cabin in Beautiful, Quiet Location
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
$119 nightly
The price is $129 total per night from Jul 12 to Jul 13
$129 total
Jul 12 - Jul 13
Total with taxes and fees
8.6/10 Excellent! (1,013 reviews)
"Staff was very professional and friendly"

Reviewed on Jul 10, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
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
$119 nightly
The price is $129 total per night from Aug 2 to Aug 3
$129 total
Aug 2 - Aug 3
Total with taxes and fees
8.4/10 Very Good! (1,013 reviews)
"The room needed updating! The toilet seat was oval shaped, the bowl was round…weird. The toilet paper dispenser was out of reach of the toilet seat, the walls needed some repairs. The breakfast was ok. The ladies working it were very nice and helpful. Overall, I won’t return there…"

Reviewed on Jul 10, 2026

Best Western Plus Keene Hotel
See all 461 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 $482 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.