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.
Homewood Suites by Hilton Albany

Homewood Suites by Hilton Albany

3 out of 5
Price was $725, price is now $651 per person
$651
per person
Jan 29 - Feb 2
found 17 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $1,042, price is now $881 per person
$881
per person
Jan 29 - Feb 2
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
The Manchester View

The Manchester View

2.5 out of 5
Price was $1,220, price is now $1,057 per person
$1,057
per person
Jan 29 - Feb 2
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
Price was $1,098, price is now $968 per person
$968
per person
Jan 29 - Feb 2
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
South Shire

South Shire

4 out of 5
Price was $757, price is now $680 per person
$680
per person
Jan 29 - Feb 2
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-in, and express check-out 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
$111 nightly
The price is $124 total per night
$124 total
Dec 9 - Dec 10
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
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
$107 nightly
The price is $120 total per night
$120 total
Dec 20 - Dec 21
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 perks like free self parking.
Pool
Hot Tub
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $120 total per night
$120 total
Jan 7 - Jan 8, 2026
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
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $208 total per night
$208 total
Dec 10 - Dec 11
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
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
$92 nightly
The price is $103 total per night
$103 total
Dec 12 - Dec 13
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $100 total per night
$100 total
Dec 15 - Dec 16
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
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 $651. 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