Windsor Vacations from $559

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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
Price was $715, price is now $559 per person
$559
per person
Jul 9 - Jul 13
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Manchester (MHT)
8.8/10 Excellent! (182 reviews)
Was nice and clean and modernized. A table in the room to do office type work at a desk could be helpful. Microwave and coffee maker too.

Reviewed on May 25, 2026

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Price was $824, price is now $596 per person
$596
per person
Jul 9 - Jul 13
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Manchester (MHT)
9.2/10 Wonderful! (213 reviews)
First time staying at this place with my family and we had a very pleasant experience! Place is very clean and peaceful. The pool as well as the barbecue area are very well maintained. And the staff from the moment we arrived to the moment we checked out, were extremely nice and pleasant! I would recommend this place 100%.

Reviewed on May 28, 2026

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,873, price is now $1,546 per person
$1,546
per person
Jul 9 - Jul 13
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
9.4/10 Exceptional! (578 reviews)
Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel.

Reviewed on May 22, 2026

Eagle Mountain House & Golf Club

Eagle Mountain House & Golf Club

3.5 out of 5
Price was $875, price is now $733 per person
$733
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Manchester (MHT)
8.8/10 Excellent! (1,003 reviews)
Loved the historical significance and serenity! Beautiful location and they have a nice bar, restaurant and pool. The lobby is very welcoming and when they don’t serve breakfast in the dining room they put out a simple but nice take it with you treat of yogurt and fruit, juice and bagels. You really have everything you need there. Golfers will have something to do as well, there is a 9 hole course on the property. If you are a family of skiers stay at Eagle Mountain House in the winter and Ski Black Mountain, you will have memories that you will cherish a lifetime.

Reviewed on May 18, 2026

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $888, price is now $747 per person
$747
per person
Jul 9 - Jul 13
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.6/10 Excellent! (883 reviews)
Great location downtown near good restaurants. The hotel is old and full of character and history. Microwave, good shower, many cable TV channels, refrigerator, elevator- all in good order. With a cinema and restaurant in the lobby. We watched a movie (The Sheep Detectives).

Reviewed on May 29, 2026

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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
$148 nightly
The price is $161 total per night from Jun 7 to Jun 8
$161 total
Jun 7 - Jun 8
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
"This place is a dump Pretty much a motel Looks and smells dirty The curtains in bathroom are filthy The tub is disgusting and black No pride in the upkeep of this property Dirty walls and carpets Exposed outlets Didn’t even clean our room I only stayed here because Hampton inn was sold out NEVERRR ..."

Reviewed on May 25, 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
$97 nightly
The price is $105 total per night from Jun 1 to Jun 2
$105 total
Jun 1 - Jun 2
Total with taxes and fees
7/10 Good! (1,000 reviews)
"The building needs a total rehab"

Reviewed on May 28, 2026

Days Inn by Wyndham Keene NH
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
$156 nightly
The price is $169 total per night from Jun 21 to Jun 22
$169 total
Jun 21 - Jun 22
Total with taxes and fees
8.8/10 Excellent! (185 reviews)
"Was nice and clean and modernized. A table in the room to do office type work at a desk could be helpful. Microwave and coffee maker too."

Reviewed on May 25, 2026

Hideaway Inn Mt.Sunapee
See all 473 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 $559 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.