Windsor Vacations from $746

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Stonybrook Motel & Lodge

Stonybrook Motel & Lodge

2 out of 5
Save 100% on your flight
Price was $1,138, price is now $746 per person
$746
per person
Sep 19 - Sep 26
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
7.6/10 Good! (1,002 reviews)
Go elsewhere

Reviewed on Jul 10, 2026

The Village of Loon Mountain Fixed Rooms

The Village of Loon Mountain Fixed Rooms

2 out of 5
Save 100% on your flight
Price was $1,581, price is now $930 per person
$930
per person
Sep 19 - Sep 26
found 8 hours 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

The Village of Loon Mountain

The Village of Loon Mountain

3 out of 5
Save 100% on your flight
Price was $1,403, price is now $952 per person
$952
per person
Sep 19 - Sep 26
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
8.6/10 Excellent! (583 reviews)
The property is out dated with soft beds and not much to do on the property for adults. Our entry door had spider webs and so did the patio. We hear a loud noise every 20 to 30 minutes and it was coming from the basement. Definitely would not stay here again.

Reviewed on Jul 10, 2026

Tiny Home Topline

Tiny Home Topline

2 out of 5
Save 100% on your flight
Price was $7,655, price is now $5,434 per person
$5,434
per person
Sep 19 - Sep 26
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
No reviews

The Chandler Inn Bethlehem - Littleton, an Ascend Collection Hotel

The Chandler Inn Bethlehem - Littleton, an Ascend Collection Hotel

3 out of 5
Save 100% on your flight
Price was $1,306, price is now $942 per person
$942
per person
Sep 19 - Sep 26
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
8.6/10 Excellent! (813 reviews)
Great service Friendly staff

Reviewed on Jul 9, 2026

Don't see what you're looking for?
See all available trips from Columbus to Windsor
View all trips

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 19 to Jul 20
$129 total
Jul 19 - Jul 20
Total with taxes and fees
8.6/10 Excellent! (1,014 reviews)
"The hotel and grounds are clean and well maintained. The staff were friendly and helpful. Room was large. Bed comfortable. Good hot shower. Good hotel breakfast. Pool was clean and nice. Ample parking. Good location. I would recommend and definitely stay here again next time in Keene. Very good ..."

Reviewed on Jul 13, 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 Jul 14 to Jul 15
$129 total
Jul 14 - Jul 15
Total with taxes and fees
8.4/10 Very Good! (1,017 reviews)
"The room, including the bathroom, was very clean. The shower was super clean. The breakfast was amazing! The lady who gets the food ready does a phenomenal job."

Reviewed on Jul 12, 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $746 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.