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.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was $437, price is now $343 per person
$343
per person
Oct 2 - Oct 5
found 7 hours ago
Roundtrip flight included
Chicago (MDW) to New Haven (HVN)
Free WiFi in public areas is available at this hotel. Business travelers can take advantage of the business center. Take advantage of the free self parking.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $532, price is now $396 per person
$396
per person
Oct 2 - Oct 5
found 7 hours ago
Roundtrip flight included
Chicago (MDW) 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.
Head of Pond House

Head of Pond House

3 out of 5
Price was $892, price is now $732 per person
$732
per person
Oct 2 - Oct 5
found 7 hours ago
Roundtrip flight included
Chicago (MDW) 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.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $1,260, price is now $995 per person
$995
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $802, price is now $633 per person
$633
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to New Haven (HVN)
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

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
$169 nightly
The price is $194 total per night
$194 total
Aug 7 - Aug 8
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
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
$122 nightly
The price is $141 total per night
$141 total
Jul 19 - Jul 20
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
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
$159 nightly
The price is $183 total per night
$183 total
Aug 1 - Aug 2
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
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
$143 nightly
The price is $164 total per night
$164 total
Aug 2 - Aug 3
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
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Free Cancellation
$78 nightly
The price is $89 total per night
$89 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. 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.
Pool
Breakfast included
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $120 total per night
$120 total
Jul 14 - Jul 15
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

Windsor Arts Center

7.6/10 (18 reviews)
Enjoy an outing to Windsor Arts Center during your stay in Windsor. Experience the area's acclaimed theater scene or attend a sporting event.
See properties

Frequently asked questions

How much are vacation packages to Windsor?
Travelocity has flight and hotel packages from as low as $343. 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 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.'
A serene lake with a red barn and a covered structure reflecting in the water, surrounded by lush trees.
A rustic metal bridge over a murky river, surrounded by leafless trees and a fence.