Deals on vacations and trips to Windsor

Save when you book Windsor package deals

Choose two or more items and save on your trip:

Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $705, price is now $589 per person
$589
per person
Dec 3 - Dec 7
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.
The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $1,095, price is now $786 per person
$786
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.
Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Price was $1,155, price is now $882 per person
$882
per person
Dec 3 - Dec 7
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.
Kingston Carriage House

Kingston Carriage House

4 out of 5
Rondout
Price was $1,052, price is now $863 per person
$863
per person
Dec 3 - Dec 7
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
This bed & breakfast features free WiFi in public areas, a communal living room, and concierge services. A virtual front desk are provided for your convenience.
Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was $828, price is now $687 per person
$687
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
A 24-hour gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like full breakfast and WiFi in public areas. A business center, a terrace, and a garden are also on offer.

Top Windsor hotels deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $123 total per night
$123 total
Nov 1 - Nov 2
Total with taxes and fees
This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Parking included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
Nov 1 - Nov 2
Total with taxes and fees
This aparthotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
$106 nightly
The price is $118 total per night
$118 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $151 total per night
$151 total
Nov 1 - Nov 2
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
$119 nightly
The price is $133 total per night
$133 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Enjoy the hot tub and free perks like continental breakfast and free self parking.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$209 nightly
The price is $233 total per night
$233 total
Nov 1 - Nov 2
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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?
Treat yourself to a one-of-a-kind experience in Windsor with a vacation package starting from as low as $589. Locking in your hotels, flights and tours through Travelocity is so simple. On top of that, our package deals will leave you with more money in your pocket for fun activities.
Where can I get the best vacation package deals for Windsor?
For a fun and affordable package deal to Windsor, turn to Travelocity. Take your pick of 400 partner airlines and 1,000,000 properties across the globe to create the ideal escape — the choice is all yours!
Why should I purchase my Windsor vacation bundle with Travelocity?
By booking your hotel, flights, activities and car rental altogether, you'll save time and money. We offer round-the-clock customer support, and you'll know that you'll always be getting the best deal in town with our Price Match Guarantee. So, what's stopping you? Book the vacation of your dreams today and start packing!
Can I save money on my Windsor car rental if I bundle 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 many things to do in and around Windsor, that rental vehicle will come in handy. Once you've slid into the driver's seat, turn up the stereo and head toward Fenway Park, an unmissable sight approximately 100 mi from Windsor.
Which airport is best for Windsor?
Bradley Intl. Airport (BDL), located around 45 mi southeast of downtown Windsor, is likely to be where you'll step off the plane. Your other choices are Albany Intl. Airport (ALB) (40 mi away from central Windsor) and Hartford, CT (HFD-Hartford - Brainard) (55 mi away from central Windsor).
Where should I stay when visiting Windsor?
The Massachusetts Vacation Rental w/ Deck & Grill is the first choice of many travelers. Book soon before it's too late.

Photos of local treasures

Browse Windsor vacation photos for more inspiration