Deals on vacations and trips to Windsor

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Super 8 by Wyndham Latham/Albany Airport

Super 8 by Wyndham Latham/Albany Airport

2 out of 5
Price was $663, price is now $611 per person
$611
per person
Nov 7 - Nov 12
found 5 hours ago
Roundtrip non-stop flight included
Kingston (KIN) to Albany (ALB)
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. Staff at the 24-hour front desk can provide around-the-clock assistance.
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

2.5 out of 5
Price was $864, price is now $749 per person
$749
per person
Nov 7 - Nov 12
found 5 hours ago
Roundtrip non-stop flight included
Kingston (KIN) to Albany (ALB)
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

2.5 out of 5
Price was $882, price is now $777 per person
$777
per person
Nov 7 - Nov 12
found 5 hours ago
Roundtrip non-stop flight included
Kingston (KIN) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $881, price is now $787 per person
$787
per person
Nov 7 - Nov 12
found 5 hours ago
Roundtrip non-stop flight included
Kingston (KIN) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. A computer station, dry cleaning, and luggage storage are also on offer.
Microtel Inn & Suites by Wyndham Amsterdam

Microtel Inn & Suites by Wyndham Amsterdam

2.5 out of 5
Price was $834, price is now $764 per person
$764
per person
Nov 7 - Nov 12
found 5 hours ago
Roundtrip non-stop flight included
Kingston (KIN) to Albany (ALB)
A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

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
$112 nightly
The price is $125 total per night
$125 total
Nov 2 - Nov 3
Total with 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
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $108 total per night
$108 total
Nov 2 - Nov 3
Total with taxes and fees
This lodge 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.
Pool
Hot Tub
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
$129 nightly
The price is $144 total per night
$144 total
Nov 2 - Nov 3
Total with 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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $98 total per night
$98 total
Nov 2 - Nov 3
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.
Pet friendly
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
$180 nightly
The price is $202 total per night
$202 total
Nov 6 - Nov 7
Total with taxes and fees
This smoke-free 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. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Spa
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
$199 nightly
The price is $223 total per night
$223 total
Nov 5 - Nov 6
Total with 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
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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 $611. 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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