Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

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Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $920, price is now $708 per person
$708
per person
Jun 15 - Jun 20
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $2,175, price is now $1,563 per person
$1,563
per person
Jul 17 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Price was $6,306, price is now $4,738 per person
$4,738
per person
Jul 17 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
A sauna, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room, a picnic area, and free newspapers are also on offer.
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3 out of 5
Price was $3,764, price is now $2,923 per person
$2,923
per person
Jul 17 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3 out of 5
Price was $4,521, price is now $3,549 per person
$3,549
per person
Jul 17 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
This cottage includes free WiFi in public areas and barbecue grills.

Top Windsor hotels deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $126 total per night
$126 total
May 24 - May 25
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $121 total per night
$121 total
May 10 - May 11
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
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
May 10 - May 11
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
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd South Deerfield MA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $110 total per night
$110 total
May 31 - Jun 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Pet friendly
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $208 total per night
$208 total
May 17 - May 18
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.
Pool
Spa
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
$145 nightly
The price is $162 total per night
$162 total
May 10 - May 11
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
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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 $708. 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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