Deals on vacations and trips to Windsor

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Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
per person
Aug 15 - Aug 18
found 11 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Albany (ALB)
This hotel features 2 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the free buffet breakfast each morning.
La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
per person
Aug 15 - Aug 18
found 11 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Albany (ALB)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Aug 15 - Aug 18
found 11 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Albany (ALB)
This hotel features an indoor pool, A 24-hour gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free airport shuttle. Unwind with a drink at the bar/lounge and enjoy perks like free self parking and a free area shuttle.
Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
per person
Aug 15 - Aug 18
found 11 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Albany (ALB)
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a grocery/convenience store, and a lobby fireplace are also on offer.
Renaissance Albany Hotel

Renaissance Albany Hotel

3.5 out of 5
Downtown Albany
per person
Aug 15 - Aug 18
found 11 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Albany (ALB)
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 free airport shuttle. Self parking, a garden, and a hair salon are also offered.

Top Windsor hotels deals

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $160 total per night
$160 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and perks like free self parking and free WiFi. A communal living room, express check-out, and luggage storage are also on offer.
Pool
Hot Tub
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
$117 nightly
The price is $131 total per night
$131 total
Jul 6 - Jul 7
Total includes taxes and fees
This condo 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
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $79 total per night
$79 total
Jul 6 - Jul 7
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
$230 nightly
The price is $257 total per night
$257 total
Jul 15 - Jul 16
Total includes taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking, a coffee shop, and a terrace are also offered.
Pet friendly
Parking included
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Free Cancellation
Reserve now, pay when you stay
$167 nightly
The price is $186 total per night
$186 total
Jul 9 - Jul 10
Total includes taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $122 total per night
$122 total
Jul 6 - Jul 7
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
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.

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 $518. 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

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