Windsor Vacations from $434

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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.
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
Save 100% on your flight
Price was $617, price is now $434 per person
$434
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MHT)
8.8/10 Excellent! (207 reviews)
So it's a virtual thing. So there is no front desk. Trying to check in was horrible. Thank God for the housekeeper. The rooms we had did smell like a dog kennel. It was a gross smell. The rooms could use some furniture. There is a bed, two chairs and a mirror. That's it. No screen on the window. Oh and a record player that hangs on the wall. I will not be staying there again. But like I said the housekeeper was an amazing lady. Thank you for your help.

Reviewed on Jul 7, 2026

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Save 100% on your flight
Price was $674, price is now $472 per person
$472
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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

Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Save 100% on your flight
Price was $838, price is now $594 per person
$594
per person
Sep 28 - Oct 5
found 1 hour ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
9.4/10 Exceptional! (123 reviews)
Very friendly and courteous owner, great location 5 mins away from Mount Snow.

Reviewed on Jul 10, 2026

The Village of Loon Mountain Fixed Rooms

The Village of Loon Mountain Fixed Rooms

2 out of 5
Price was $651, price is now $474 per person
$474
per person
Oct 5 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
8.6/10 Excellent! (53 reviews)
Plenty of towels and bedding. The two pools and multiple hot tubs, and sauna provided great after skiing entertainment. The shuttle didn't run for NH vacation week but it's an easy drive across street to mountain. The staff stayed on top of plowing and shoveling. The electric heat is a little erratic in the unit with the loft sometimes feeling like summer. Front desk is well staffed and ready to assist.

Reviewed on Feb 26, 2026

Eagle Mountain House & Golf Club

Eagle Mountain House & Golf Club

3.5 out of 5
Save 100% on your flight
Price was $770, price is now $571 per person
$571
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MHT)
8.8/10 Excellent! (1,002 reviews)
My wife and I had a great 3 day stay place is very well kept and the staff is friendly. We love hanging out on the front porch.

Reviewed on Jul 10, 2026

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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?
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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 468 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 $434 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.