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Our top choices for Rutland vacation homes

Arcade/Fireplace/CoffeeBar The Holidays Start Here
Arcade/Fireplace/CoffeeBar The Holidays Start HereMilton
10.0 out of 10, Exceptional, (17)
$504 nightly
The price is $557
Dec 16 - Dec 17
Total with taxes and fees

One Bedroom Queen in the heart of downtown.
One Bedroom Queen in the heart of downtown.Downtown Madison
10.0 out of 10, Exceptional, (2)
$193 nightly
The price is $223
Dec 17 - Dec 18
Total with taxes and fees

Waterfront - Hot Tub - Sauna - Game Room - Pets
Waterfront - Hot Tub - Sauna - Game Room - PetsEdgerton
8.8 out of 10, Excellent, (5)
$681 nightly
The price is $700
Dec 16 - Dec 17
Total with taxes and fees

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Charming 3-bedroom Duplex unit with WiFi in Cottage GroveVillage of Cottage Grove
10.0 out of 10, Exceptional, (7)
$397 nightly
The price is $450
Jan 11 - Jan 12, 2026
Total with taxes and fees

Doty ★ Walk to Everything -Hotel Quality- Downtown
Doty ★ Walk to Everything -Hotel Quality- DowntownDowntown Madison
9.8 out of 10, Exceptional, (37)
$240 nightly
The price is $277
Dec 16 - Dec 17
Total with taxes and fees

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!Monona
9.8 out of 10, Exceptional, (47)
$439 nightly
The price is $498
Dec 16 - Dec 17
Total with taxes and fees

Winter Wonderland | Near UW + Skiing
Winter Wonderland | Near UW + SkiingFitchburg
10.0 out of 10, Exceptional, (19)
$698 nightly
The price is $785
Dec 16 - Dec 17
Total with taxes and fees

One Bedroom King with views of the heart of downtown.
One Bedroom King with views of the heart of downtown.Downtown Madison
10.0 out of 10, Exceptional, (2)
$205 nightly
The price is $237
Dec 16 - Dec 17
Total with taxes and fees
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 Rutland Hotel Reviews

The Madison Concourse Hotel and Governor's Club
10/10 Excellent
Find out more about Rutland
Rutland Vacation Homes information
Number of reviews | 136 |
|---|---|
Accommodation | 98 Vacation Homes |
Lowest Price | $208 |
Highest Price | $785 |
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