Darlington Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Darlington Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Valued Stay Sun Prairie
Price was $597, price is now $537 per person
$537
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Madison (MSN)
Stay at this hotel in Sun Prairie. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions East Towne Mall and Sun Prairie Family Aquatic Center are located nearby.
The Edgewater
Downtown Madison
Save 100% on your flight
Price was $1,842, price is now $1,429 per person
$1,429
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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 Capitol Square and Kohl Center are located nearby.
Right on lake Mendota. Very nice and clean.
Reviewed on Jul 27, 2026
Graduate by Hilton Madison
Downtown Madison
Price was $1,425, price is now $1,249 per person
$1,249
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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 Kohl Center and Capitol Square are located nearby.
Great roof top bar and food
Reviewed on Jul 25, 2026
Fairfield Inn & Suites by Marriott Madison East
Price was $996, price is now $874 per person
$874
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions East Towne Mall and Capitol Square are located nearby.
The room was real clean & comfortable. Note the room was warm & stuffy when you first walk in. It must have a smart thermostat. It cooled right away. I wished we had time to visit the hot tub. I try to pick a hotel with a hot tub. The breakfast had good variety of choices.
Reviewed on Jul 20, 2026
AmericInn by Wyndham Madison South
Monona
Price was $771, price is now $690 per person
$690
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Alliant Energy Center and Capitol Square are located nearby.
Room was very clean had one the best night sleeps
The last two nights, staff was very helpful and kind, will be staying there m again my new home away from home
Reviewed on Jul 27, 2026
Country Inn & Suites by Radisson, Madison Southwest, WI
Price was $797, price is now $720 per person
$720
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Camp Randall Stadium and Alliant Energy Center are located nearby.
Nice quiet hotel in Fitchburg, WI with a unique restaurant next door called Quivys, with good food, Madison minutes away. The hotel is a little older but everything was nice and the pool and hot tub a nice ending to a long day. The beds were a bit firm for me and air conditioner a bit loud but it kept the room cool and I did get to sleep. Breakfast was a plus to get your day going, staff was very friendly and helpfull
Reviewed on Jul 27, 2026
Top Hotel Deals
Darlington Inn
201 Christiensen Dr Darlington WI
3.81 km from city center
Book a stay at this business-friendly motel in Darlington. Enjoy free breakfast, free WiFi, and free parking.
Irish Cottage Inn & Suites
9853 US-20 Galena IL
41.09 km from city center
Stay at this hotel in Galena. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
Wyndham Garden Galena Hotel & Day Spa
11383 US Highway 20 Galena IL
40.24 km from city center
Book a stay at this spa hotel in Galena. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
Stoney Creek Inn Galena
940 Galena Square Dr Galena IL
41.07 km from city center
Book a stay at this business-friendly hotel in Galena. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Country Inn & Suites by Radisson, Galena, IL
11334 Oldenburg Ln Galena IL
40.21 km from city center
Book a stay at this family-friendly hotel in Galena. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Don Q Inn
3658 State Road 23 Dodgeville WI
33.16 km from city center
Stay at this hotel in Dodgeville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Best Western Galena Inn & Suites
9923 West US Route 20 Galena IL
41.16 km from city center
Stay at this hotel in Galena. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Grant Hills Motel
9372 US Hwy 20 W Galena IL
40.65 km from city center
Book a stay at this business-friendly hotel in Galena. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Eagle Ridge Resort Golf and Horseshoe ...
Hotel Galena
324 Spring St Galena IL
41.41 km from city center
Stay at this hotel in Galena. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Dodgeville inn and suites
1308 n johns st Dodgeville WI
31.23 km from city center
Stay at this hotel in Dodgeville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cox Hollow Beach and Governor Dodge State Park are located ...
AmericInn by Wyndham Dodgeville
3637 State Road 23 Dodgeville WI
32.92 km from city center
Book a stay at this business-friendly hotel in Dodgeville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Eagle Ridge Resort and Spa
444 Eagle Ridge Dr Galena IL
37.52 km from city center
Book a stay at this spa resort in Galena. Enjoy a full-service spa, 3 restaurants, and a marina. Popular attractions Eagle Ridge Resort Golf and Horseshoe Mound ...
Deer Valley Lodge & Golf
401 West Industrial Drive Barneveld WI
38.38 km from city center
Book a stay at this golf hotel in Barneveld. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Sep 11 - Fri, Sep 18
DEN
Denver Intl.
MSN
Dane County Regional
$190 Roundtrip, found 4 days ago
$190
Roundtrip
found 4 days ago
Sat, Sep 12 - Sat, Sep 19
DEN
Denver Intl.
MSN
Dane County Regional
$279 Roundtrip, found 3 days ago
$279
Roundtrip
found 3 days ago
Sat, Sep 12 - Sat, Sep 19
DEN
Denver Intl.
MSN
Dane County Regional
$299 Roundtrip, found 3 days ago
$299
Roundtrip
found 3 days ago
Sat, Sep 12 - Sat, Sep 19
DEN
Denver Intl.
MSN
Dane County Regional
$299 Roundtrip, found 3 days ago
$299
Roundtrip
found 3 days ago
Sat, Sep 19 - Tue, Sep 29
LAS
Harry Reid Intl.
MSN
Dane County Regional
$607 Roundtrip, found 2 days ago
$607
Roundtrip
found 2 days ago