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.
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
Price was $463, price is now $454 per person
$454
per person
Nov 24 - Nov 27
just found
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. A snack bar/deli, express check-out, and laundry facilities are also on offer.
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 17 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.
Days Inn by Wyndham Ridgefield

Days Inn by Wyndham Ridgefield

2 out of 5
Price was $742, price is now $680 per person
$680
per person
Nov 24 - Nov 28
just found
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and free newspapers are also on offer.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $679, price is now $633 per person
$633
per person
Nov 24 - Nov 27
just found
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Head of Pond House

Head of Pond House

3 out of 5
Price was $1,110, price is now $1,046 per person
$1,046
per person
Dec 30 - Jan 3
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a communal living room are also on offer.

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.
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.
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.
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.
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
$110 nightly
The price is $126 total per night
$126 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.
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $104 total per night
$104 total
Nov 16 - Nov 17
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.
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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 $454. 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.'