Title: Windsor Vacation Packages 2026 from $530 | Expedia.com

[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d553248634998834412.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d553248634998834412.Travel-Guide-VacationRentals)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d553248634998834412.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Windsor Vacations from $530

## Book a Hotel + Flight or Car together to unlock savings

## 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](https://www.expedia.com/Franklin-Pierce-Homestead-Hillsboro.d6110846.Vacation-Attraction) 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.

![The Centennial](https://images.trvl-media.com/lodging/1000000/50000/42700/42642/e7221520_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Centennial

$530

per person

Apr 23 - Apr 26

found 1 day ago

Roundtrip non-stop flight included

Orlando (ORL) to Manchester (MHT)

8.8/10 Excellent! (1,000 reviews)

The breakfast was very bad, only cold items and staled bread.

Reviewed on Feb 16, 2026

![Anchor at Tideline](https://images.trvl-media.com/lodging/119000000/118120000/118114000/118113913/4a0be860_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Anchor at Tideline

$598

per person

Apr 16 - Apr 22

found 1 day ago

Roundtrip flight included

San Francisco (SFO) to Manchester (MHT)

9.4/10 Exceptional! (3 reviews)

Beautiful room and very clean!

Reviewed on Feb 12, 2026

![Holiday Inn Express Durham by IHG](https://images.trvl-media.com/lodging/2000000/1510000/1507300/1507215/941e3cbf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn Express Durham by IHG

$602

per person

Apr 16 - Apr 22

found 1 day ago

Roundtrip flight included

San Francisco (SFO) to Manchester (MHT)

8.6/10 Excellent! (883 reviews)

we had a quick 1 night stay in town for an event. room was great, breakfast variety was amazing. kids had a good time

Reviewed on Feb 21, 2026

![The Hotel Concord](https://images.trvl-media.com/lodging/27000000/27000000/26999700/26999690/23da57c3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Hotel Concord

Downtown Concord

$692

per person

Apr 23 - Apr 26

found 1 day ago

Roundtrip non-stop flight included

Orlando (ORL) to Manchester (MHT)

9.6/10 Exceptional! (519 reviews)

Yes, everything was perfect

Reviewed on Feb 22, 2026

![The Grand at Bedford Village Inn](https://images.trvl-media.com/lodging/2000000/1220000/1211400/1211321/f6604c5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Grand at Bedford Village Inn

$775

per person

May 22 - May 24

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Manchester (MHT)

9.6/10 Exceptional! (352 reviews)

Everything was above and beyond. Our room was lovely. Every staff member was great! I would highly recommend the BVI.

Reviewed on Jan 29, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windsor

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-26/2026-04-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=VSF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_553248634998834412)

### 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. 

[](https://expedia.com/Franklin-Pierce-Homestead-Hillsboro.d6110846.Vacation-Attraction)

#### 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. 

[](https://expedia.com/Eatons-Magic-Morsel-Hillsboro.d553248621532666952.Vacation-Attraction)

## Windsor Hotel Deals

![Hideaway Inn Mt.Sunapee](https://images.trvl-media.com/lodging/121000000/120350000/120341300/120341253/7f350a77_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hideaway Inn Mt.Sunapee

1403 New Hampshire Rte 103 Newbury NH

Fully refundableReserve now, pay when you stay

$136 nightly

$148 total

Mar 17 - Mar 18

Total with taxes and fees

8.8/10 Excellent! (123 reviews)

We had a great stay and the staff was super helpful.

Reviewed on Feb 26, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F17%2F2026&endDate=3%2F18%2F2026&selected=120341253&PinnedHotelID=120341253&HadPinnedHotel=true&regionId=553248634998834412)

![Days Inn by Wyndham Keene NH](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

Fully refundableReserve now, pay when you stay

$81 nightly

$88 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://expedia.com/Hotel-Search?startDate=2%2F28%2F2026&endDate=3%2F1%2F2026&selected=50340&PinnedHotelID=50340&HadPinnedHotel=true&regionId=553248634998834412)

![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Best Western Plus Keene Hotel

401 Winchester St Keene NH

Fully refundableReserve now, pay when you stay

$119 nightly

$129 total

Feb 27 - Feb 28

Total with taxes and fees

8.4/10 Very Good! (1,001 reviews)

The room was not clean. There was a big spill of some kind of oil on the nightstand. Really gross!!!

Reviewed on Feb 23, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F27%2F2026&endDate=2%2F28%2F2026&selected=15916&PinnedHotelID=15916&HadPinnedHotel=true&regionId=553248634998834412)

[See all 449 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F27%2F2026&endDate=2%2F28%2F2026&regionId=553248634998834412)

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?

### What are the cheapest months to go to Windsor?

### How many days is enough for Windsor?

### How to find the best Windsor package deals?

### Is it cheaper to book a Windsor vacation as a package?

### When to book a vacation package to Windsor?

### Does Expedia offer Book Now, Pay Later Windsor vacation packages?

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.