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Windsor Vacation Packages

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Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
Price was $606, price is now $510 per person
$510
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool in our reviews. Popular attractions Camp Randall Stadium and Alliant Energy Center are located nearby.
Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Price was $661, price is now $538 per person
$538
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy a rooftop terrace, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Camp Randall Stadium and Alliant Energy Center are located nearby.
The Edgewater

The Edgewater

4.5 out of 5
Price was $801, price is now $657 per person
$657
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)
Book a stay at this luxury hotel in Madison. Enjoy a full-service spa, 4 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Camp Randall Stadium and Alliant Energy Center are located nearby.
Christmas Mountain Campground

Christmas Mountain Campground

3 out of 5
Price was $762, price is now $626 per person
$626
per person
May 19 - May 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Madison (MSN)
Book a stay at this ski resort in Wisconsin Dells. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Kalahari Indoor Waterpark and Mt. Olympus Water and Theme Park are located nearby.
Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Price was $711, price is now $598 per person
$598
per person
May 23 - May 26
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Camp Randall Stadium and Alliant Energy Center are located nearby.
The Saddlery Madison Downtown

The Saddlery Madison Downtown

2 out of 5
Price was $952, price is now $807 per person
$807
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)
Stay at this hotel in Madison. Enjoy free WiFi, parking (surcharge), and laundry facilities. Popular attractions Camp Randall Stadium and Alliant Energy Center are located nearby.
Embassy Suites By Hilton Madison Downtown

Embassy Suites By Hilton Madison Downtown

3.5 out of 5
Price was $956, price is now $826 per person
$826
per person
May 21 - May 25
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)
Stay at this hotel in Madison. Enjoy free breakfast, free WiFi, and room service. Popular attractions Camp Randall Stadium and Alliant Energy Center are located nearby.
Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

3 out of 5
Price was $751, price is now $653 per person
$653
per person
May 19 - May 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Madison (MSN)
Book a stay at this ski resort in Wisconsin Dells. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Kalahari Indoor Waterpark and Mt. Olympus Water and Theme Park are located nearby.

Windsor Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
Downtown Madison
Price was $606, price is now $510 per person
$510
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)
Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
Price was $661, price is now $538 per person
$538
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)
The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Price was $801, price is now $657 per person
$657
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)
Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was $711, price is now $598 per person
$598
per person
May 23 - May 26
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)

Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Christmas Mountain Campground

Christmas Mountain Campground

3 out of 5
Price was $762, price is now $626 per person
$626
per person
May 19 - May 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Madison (MSN)
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
Downtown Madison
Price was $1,019, price is now $796 per person
$796
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Madison (MSN)
Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

3 out of 5
Price was $751, price is now $653 per person
$653
per person
May 19 - May 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Madison (MSN)
Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
Price was $2,943, price is now $2,564 per person
$2,564
per person
May 6 - May 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Bargain Flight
Thu, Aug 20 - Tue, Aug 25
BOS
Logan Intl.
MSN
Dane County Regional
$257 Roundtrip, found 19 hours ago
$257
Roundtrip
found 19 hours ago
Select Bargain Flight flight, departing Thu, Aug 20 from Logan Intl. to Dane County Regional, returning Tue, Aug 25, priced at $257 found 19 hours ago
Bargain Flight
Wed, Jun 24 - Tue, Jun 30
LAS
Harry Reid Intl.
MSN
Dane County Regional
$261 Roundtrip, found 1 hour ago
$261
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Wed, Jun 24 from Harry Reid Intl. to Dane County Regional, returning Tue, Jun 30, priced at $261 found 1 hour ago
United
Sat, Sep 12 - Tue, Sep 29
DEN
Denver Intl.
MSN
Dane County Regional
$269 Roundtrip, found 23 hours ago
$269
Roundtrip
found 23 hours ago
Select United flight, departing Sat, Sep 12 from Denver Intl. to Dane County Regional, returning Tue, Sep 29, priced at $269 found 23 hours ago
Bargain Flight
Tue, Apr 7 - Sat, Apr 11
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$276 Roundtrip, found 1 hour ago
$276
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Tue, Apr 7 from Minneapolis - St. Paul Intl. to Dane County Regional, returning Sat, Apr 11, priced at $276 found 1 hour ago