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Middleton Vacation Packages

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Middleton Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Price was $719, price is now $623 per person
$623
per person
Nov 22 - Nov 26
found 21 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Everything was amazing here !!

Reviewed on Oct 20, 2026

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
Price was $1,186, price is now $977 per person
$977
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

Days Inn & Suites by Wyndham Madison

Days Inn & Suites by Wyndham Madison

2 out of 5
Price was $839, price is now $727 per person
$727
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Madison (MSN)
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Alliant Energy Center and East Towne Mall are located nearby.
everything was perfect

Reviewed on Oct 20, 2026

Madison Marriott South

Madison Marriott South

3.5 out of 5
Price was $1,125, price is now $1,039 per person
$1,039
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Alliant Energy Center and Camp Randall Stadium are located nearby.
Very nice hotel

Reviewed on Oct 16, 2026

1810 Emerson House Bed & Breakfast - Adults Only

1810 Emerson House Bed & Breakfast - Adults Only

3.5 out of 5
Price was $847, price is now $789 per person
$789
per person
Nov 23 - Nov 27
found 12 hours ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
Stay at this B&B in Beloit. Enjoy free WiFi, free parking, and a garden. Popular attractions Hancock Field and Rosevelt Park are located nearby.
Simply the BEST stay! Tony and Beth are the kindest hosts! The space is cozy and intimate; perfect for special occasions. My husband and I have had the privilege of staying here 3 times, and this will always be one of our favorite spots for a getaway! We highly recommend this gem!

Reviewed on Mar 22, 2026

Wingate by Wyndham Wisconsin Dells Waterpark

Wingate by Wyndham Wisconsin Dells Waterpark

3 out of 5
Price was $1,108, price is now $1,033 per person
$1,033
per person
Nov 24 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Casper (CPR) to Madison (MSN)
Book a stay at this business-friendly hotel in Baraboo. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. Popular attractions Kalahari Indoor Waterpark and Noah's Ark Waterpark are located nearby.
There needs to be a rating between 'Good' and 'Excellent'. Everything was very nice, and clean, for what we paid for, and if there were a 'Very Good' rating, I would have selected it. No complaints here.

Reviewed on Oct 18, 2026

The Edgewater

The Edgewater

4.5 out of 5
Price was $1,408, price is now $1,319 per person
$1,319
per person
Dec 6 - Dec 10
found 3 hours ago
Roundtrip flight included
Phoenix (PHX) 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.
Loved the location, right on time lake. Reasonable price

Reviewed on Oct 19, 2026

The Wisconsin Hotel & Conference Center

The Wisconsin Hotel & Conference Center

2.5 out of 5
Price was $1,275, price is now $1,200 per person
$1,200
per person
Nov 24 - Nov 28
found 22 hours ago
Roundtrip non-stop flight included
Casper (CPR) to Madison (MSN)
Book a stay at this family-friendly hotel in Wisconsin Dells. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Kalahari Indoor Waterpark and Noah's Ark Waterpark are located nearby.
Can't believe we actually found a sophisticated, classy hotel in the Dells. We'll definitely return and spread the word to family and friends.

Reviewed on Oct 19, 2026

Middleton Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was $719, price is now $623 per person
$623
per person
Nov 22 - Nov 26
found 21 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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 $723, price is now $653 per person
$653
per person
Dec 26 - Dec 29
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Madison (MSN)
1810 Emerson House Bed & Breakfast - Adults Only

1810 Emerson House Bed & Breakfast - Adults Only

3.5 out of 5
Price was $847, price is now $789 per person
$789
per person
Nov 23 - Nov 27
found 12 hours ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
Wingate by Wyndham Wisconsin Dells Waterpark

Wingate by Wyndham Wisconsin Dells Waterpark

3 out of 5
Price was $1,108, price is now $1,033 per person
$1,033
per person
Nov 24 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Casper (CPR) to Madison (MSN)

Middleton Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Days Inn & Suites by Wyndham Madison

Days Inn & Suites by Wyndham Madison

2 out of 5
Price was $839, price is now $727 per person
$727
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $1,186, price is now $977 per person
$977
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Madison (MSN)
Madison Marriott South

Madison Marriott South

3.5 out of 5
Price was $1,125, price is now $1,039 per person
$1,039
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Madison (MSN)
Holiday Inn Express & Suites Beloit by IHG

Holiday Inn Express & Suites Beloit by IHG

3.5 out of 5
Price was $786, price is now $749 per person
$749
per person
Dec 27 - Jan 1
found 22 hours ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)

Top Flight Deals

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

Bargain Flight
Wed, Nov 11 - Sat, Nov 14
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$226 Roundtrip, found 15 hours ago
$226
Roundtrip
found 15 hours ago
Select Bargain Flight flight, departing Wed, Nov 11 from Minneapolis - St. Paul Intl. to Dane County Regional, returning Sat, Nov 14, priced at $226 found 15 hours ago
Bargain Flight
Wed, Oct 28 - Sun, Nov 1
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$292 Roundtrip, found 3 hours ago
$292
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Wed, Oct 28 from Ronald Reagan Washington National to Dane County Regional, returning Sun, Nov 1, priced at $292 found 3 hours ago
Bargain Flight
Sat, Nov 14 - Tue, Nov 17
BOS
Logan Intl.
MSN
Dane County Regional
$300 Roundtrip, found 13 hours ago
$300
Roundtrip
found 13 hours ago
Select Bargain Flight flight, departing Sat, Nov 14 from Logan Intl. to Dane County Regional, returning Tue, Nov 17, priced at $300 found 13 hours ago
Bargain Flight
Mon, Nov 2 - Fri, Nov 13
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$307 Roundtrip, found 3 hours ago
$307
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Mon, Nov 2 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Fri, Nov 13, priced at $307 found 3 hours ago