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.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,181, price is now $640 per person
$640
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A steam room is featured at this hotel, along with free WiFi in public areas and dry cleaning. There's luggage storage and multilingual staff can provide around-the-clock assistance.
Tudor Lux

Tudor Lux

4 out of 5
Price was $3,432, price is now $1,753 per person
$1,753
per person
Nov 6 - Nov 8
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Philadelphia (PHL)
A terrace, a garden, and a picnic area are available at this vacation home. Families will appreciate the arcade/game room and barbecue grills. Free self parking, laundry facilities, and a virtual front desk are also on offer.
Casa De Miliki

Casa De Miliki

3 out of 5
South Philadelphia
Price was $3,357, price is now $1,841 per person
$1,841
per person
Nov 6 - Nov 8
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Philadelphia (PHL)
This guesthouse includes free WiFi in public areas and laundry facilities.
Cozy Home near City Center with Hot tub

Cozy Home near City Center with Hot tub

3 out of 5
South Philadelphia
Price was $7,031, price is now $3,973 per person
$3,973
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
This vacation home includes free WiFi in public areas and laundry facilities.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,185, price is now $684 per person
$684
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Top Windsor hotels deals

Hyatt Regency Princeton

Hyatt Regency Princeton

4 out of 5
102 Carnegie Ctr Princeton NJ
$118 nightly
The price is $135 total per night
$135 total
Oct 4 - Oct 5
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included
The Heldrich Hotel

The Heldrich Hotel

4 out of 5
10 Livingston Avenue New Brunswick NJ
Free Cancellation
Reserve now, pay when you stay
$132 nightly
The price is $150 total per night
$150 total
Sep 27 - Sep 28
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this Art Deco hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and wedding services.
Pool
Spa
MHO Hotel Bordentown

MHO Hotel Bordentown

2 out of 5
187 US 130 and 206 Bordentown NJ
Free Cancellation
Reserve now, pay when you stay
$61 nightly
The price is $69 total per night
$69 total
Oct 1 - Oct 2
Total with taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A computer station is also provided.
Parking included
Free WiFi
Hilton East Brunswick Hotel & Executive Meeting Center

Hilton East Brunswick Hotel & Executive Meeting Center

3.5 out of 5
3 Tower Center Blvd East Brunswick NJ
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $140 total per night
$140 total
Sep 22 - Sep 23
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 45 conference rooms, free WiFi in public areas, and express check-in. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.
Pool
Free WiFi
DoubleTree by Hilton Princeton

DoubleTree by Hilton Princeton

4 out of 5
4355 US Highway 1 at Ridge Rd. Princeton NJ
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $107 total per night
$107 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Unwind with a drink at the bar/lounge and enjoy perks like free self parking and a free area shuttle.
Pool
Pet friendly
Holiday Inn East Windsor - Cranbury Area by IHG

Holiday Inn East Windsor - Cranbury Area by IHG

3 out of 5
399 Monmouth St Hightstown NJ
Free Cancellation
$90 nightly
The price is $103 total per night
$103 total
Oct 18 - Oct 19
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a garden, and dry cleaning are also offered.
Parking included
Free WiFi
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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.

Frequently asked questions

How much are vacation packages to Windsor?
Starting from as low as $640, flight and hotel packages are an excellent way to make your vacation budget stretch further. Windsor, here you come!
Where can I get the best vacation package deals for Windsor?
For an amazing package deal to Windsor, you can't go past Travelocity. Take your pick of 400 partner airlines and 1,000,000 properties across the globe to create your dream escape — it's as easy as that.
Why should I book my Windsor vacation bundle with Travelocity?
Travel should be about making cherished memories and leaving all your stresses behind — which is why we provide you with a team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our impressive range of vacation packages. So what are you waiting for? There's no time like the present to secure the vacation of a lifetime.
Can I save money on my Windsor car rental if I bundle it with my hotel or flight?
Booking a Windsor vacation package with Travelocity is a surefire way to save you time and money. Combine a hotel, flight and car, or any combination of them, and enjoy great discounts. You could also throw in a few activities and experiences. After you've collected the keys to your rental car, venture out of the neighborhood and discover what this place has to offer. About 45 mi from Windsor, Times Square is well worth a road trip.

Photos of local treasures

Browse Windsor vacation photos for more inspiration

A couple standing in front of a detailed white temple facade with intricate carvings and statues.