Windsor Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Top Flight + Hotel Deals in Windsor

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
per person
15 Oct - 19 Oct
found 1 day ago
Return direct flight included
London (LHR) to New Haven (HVN)
7/10 Good! (888 reviews)
The pool wasn’t open, the room needed to be updated, bathroom outlet didn’t work, tv was static, I wouldn’t stay again.

Reviewed on 27 Jul 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
15 Oct - 19 Oct
found 1 day ago
Return direct flight included
London (LHR) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
I love this property. But, very disappointed in the pool and lack of variety of food

Reviewed on 9 Aug 2025

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
per person
15 Oct - 19 Oct
found 1 day ago
Return direct flight included
London (LHR) to New Haven (HVN)
9.4/10 Exceptional! (16 reviews)
We loved the convenient location and beautiful historic building, but we were very disappointed in the level of cleanliness (a layer of dust on shelves and fireplace, cobwebs under furniture). There were some other issues (loose shower head, broken coffee maker). There's no one on site to address in person. It's a lovely place, but needs some attention. For the price, it should be better! :(

Reviewed on 1 May 2025

The Captain Stannard

The Captain Stannard

3 out of 5
Westbrook Center
per person
15 Oct - 19 Oct
found 1 day ago
Return direct flight included
London (LHR) to New Haven (HVN)
9.6/10 Exceptional! (237 reviews)
This is as nice a place as can be. 10 stars all the way from checkin to check out. Do not hesitate to book here

Reviewed on 25 Jul 2025

The Niantic Inn

The Niantic Inn

2 out of 5
per person
15 Oct - 19 Oct
found 1 day ago
Return direct flight included
London (LHR) to New Haven (HVN)
9.2/10 Wonderful! (103 reviews)
Everything was great .Location is perfect to shop and dine. Only issue was garbage was left in stairwells overnight

Reviewed on 2 May 2025

Top hotels in Windsor

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
555 Corporate Dr, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is €125 per night from 1 Sept to 2 Sept
€125
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Nice"

Reviewed on 7 Aug 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport
Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

3.5 out of 5
28 Day Hill Rd, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is €157 per night from 15 Aug to 16 Aug
€157
15 Aug - 16 Aug
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"The airport shuttle was very helpful for our family whose flight had been cancelled."

Reviewed on 5 Aug 2025

Marriott Hartford/Windsor Airport
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
200 Corporate Dr, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is €142 per night from 24 Aug to 25 Aug
€142
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Spacious and clean. Staff was kind."

Reviewed on 3 Aug 2025

HYATT house Hartford North/Windsor
See all 666 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.

Frequently asked questions

How much does a Windsor holiday package cost?
You'll find cheap prices from €627 on Expedia for your Windsor break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your holiday to Windsor costs.
What are the cheapest months to go to Windsor?
You can typically find lower rates and greater availability in December, January and February. Explore our cheap Windsor holiday packages and you could score some great off-season discounts.
How many days is enough for Windsor?
With about 2 days, you'll have enough time to visit popular neighbourhoods like Downtown Hartford and North Meadows during your Windsor holiday. Be sure to also add Oliver Ellsworth Homestead and SS&C SummerWind Performing Arts Centre to your list of must-sees. In the mood for more adventures? Consider exploring outside of Windsor on tours and day trips.
Is it worth booking a holiday package to Windsor?
Whether you want to check out top sights such as Oliver Ellsworth Homestead and Windsor Meadows State Park on your Windsor holiday, or coming for its great history, festivals and culture, there's something for everyone here. With so many things to see and do, you'll quickly learn why so many visitors think Windsor is a good holiday destination.
How to find the best Windsor package deals?
Bagging a cheap Windsor package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can customise your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor holiday as a package?
You can enjoy significant savings on your next Windsor getaway by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Windsor?
If you're planning a spur-of-the-moment Windsor holiday, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Windsor?

  1. Pick your travel dates: What you want to do in Windsor and your preferred season will help you decide when to go.
  2. Budget wisely: Besides the price of your stay, you should consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Windsor.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Windsor. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customised Windsor holiday package.

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