
Windsor Vacations from $482
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.


Exeter Inn
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
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
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
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
Stay near popular Windsor attractions
Windsor Hotel Deals

Lakefront Cabin in Beautiful, Quiet Location
Windsor NH

Keene Elm City Hotel, an Ascend Collection Hotel
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

Best Western Plus Keene Hotel
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
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
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















