Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $673, price is now $541 per person
$541
per person
Dec 30 - Jan 3
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,652, price is now $1,011 per person
$1,011
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $740, price is now $601 per person
$601
per person
Nov 27 - Nov 30
found 7 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $886, price is now $724 per person
$724
per person
Dec 17 - Dec 21
found 7 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $823, price is now $692 per person
$692
per person
Dec 17 - Dec 21
found 7 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.

Top Windsor hotels deals

Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

3.5 out of 5
28 Day Hill Rd Windsor CT
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $183 total per night
$183 total
Nov 14 - Nov 15
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like free self parking.
Pool
Free airport shuttle
Courtyard By Marriott Hartford/Windsor Airport

Courtyard By Marriott Hartford/Windsor Airport

3 out of 5
1 Day Hill Rd Windsor CT
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $161 total per night
$161 total
Oct 22 - Oct 23
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Pet friendly
Free WiFi
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
200 Corporate Dr Windsor CT
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $155 total per night
$155 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
100 Dunfey Ln Windsor CT
Get rates
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Pool
Breakfast included
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
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $124 total per night
$124 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy free perks like free self parking and an area shuttle.
Free airport shuttle
Pet friendly
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $120 total per night
$120 total
Nov 3 - Nov 4
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-out. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
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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.

Stay near popular Windsor attractions

Loomis Chaffee School

Enjoy the collegiate vibe at Loomis Chaffee School as part of your travels around Windsor. While in this family-friendly area, you can savor the top-notch restaurants.
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Frequently asked questions

How much are vacation packages to Windsor?
Travelocity has flight and hotel packages from as low as $541. With these kinds of savings, you'll be exploring all of Windsor in the blink of an eye.
How long should my Windsor vacation be?
Most sightseers vacation in Windsor for approximately 2 nights. But traveling is all about finding new adventures and making memories — why not book a couple of more nights so you can do just that?
Where can I get the best vacation package deals for Windsor?
Travelocity can help you get a great Windsor package deal. With no less than 400 airlines and 1,000,000 properties across the globe, we know you'll find one that works for you.
Why should I book my Windsor vacation package via Travelocity?
From our 24/7 customer support to our range of enticing destinations, we're dedicated to giving you the most unforgettable escape. All you need to do is click and book — our Price Match Guarantee will ensure you get the cheapest price.
Can I save money on my Windsor car rental if I combine it with my hotel or flight?
You certainly can — combine your car, hotel and flight into a Windsor vacation package and you can save a ton. With so much to discover in Windsor, having your own set of wheels will make exploring a breeze. Once you've buckled yourself in, put the stereo on and head toward Times Square, a famous attraction around 100 mi from Windsor.
Which airport is best for Windsor?
There's a very good chance you'll be arriving at Bradley Intl. Airport (BDL), which is 6 mi north of inner Windsor. Tweed - New Haven Regional Airport (HVN) (40 mi away from central Windsor) and Hartford, CT (HFD-Hartford - Brainard) (8 mi away from central Windsor) are your other options.
What is there to do in Windsor?
Windsor is full of places to discover, including Oliver Ellsworth Homestead and Windsor Meadows State Park. These well-known attractions are on most tourists' must-see lists.
Where should I stay when visiting Windsor?
If you're after a place to spend your nights, take a look at the Hilton Garden Inn Hartford North/Bradley Intl Airport. It's the top choice for many travelers.

Photos of local treasures

Browse Windsor vacation photos for more inspiration

A rustic barn surrounded by autumn foliage and a field.
A frozen river with snow-covered trees on both sides.
A frozen river with trees in the foreground and houses in the background.
A calm river with autumn foliage reflecting on the water, surrounded by dense forest.
A covered bridge over a river with a sign that reads 'Walk your horses or pay two dollars fine.'