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Our top choices for Rutland vacation homes
Vacation Home in Milton
Arcade/Fireplace/CoffeeBar The Holidays Start Here10.0 out of 10, Exceptional, (17)
"We had the best VRBO experience at Harbor House. The hosts are absolutely fabulous. The house was perfect, just as presented online. 6 of us adults and a little French bulldog spent a long weekend there so we could cheer on our son (one of the visitors) as he ran the half Ironman in Madison. He LOVED the hot tub afterward. Great visit. Would definitely stay again if in the area."
Karrie S.
$486 nightly
The price is $537
Dec 15 - Dec 16
Total with taxes and fees
Vacation Home in Downtown Madison
One Bedroom Queen in the heart of downtown.10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay and the close location to the capital. Great modern style and very functional "
Alexandrines H.
$193 nightly
The price is $223
Dec 14 - Dec 15
Total with taxes and fees
Vacation Home in Edgerton
Waterfront - Hot Tub - Sauna - Game Room - Pets8.8 out of 10, Excellent, (5)
"Overall a really great place! Lots of space to spread out in the house and lots of fun stuff providing with the paddle boards, kayaks, and games. The back deck is huge, but could use a good cleaning. I would recommend this place. "
Jessica D.
$681 nightly
The price is $700
Dec 16 - Dec 17
Total with taxes and fees
Vacation Home in Village of Cottage Grove
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove10.0 out of 10, Exceptional, (7)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
Anakin F.
$397 nightly
The price is $450
Jan 11 - Jan 12, 2026
Total with taxes and fees
Vacation Home in Downtown Madison
Doty ★ Walk to Everything -Hotel Quality- Downtown9.8 out of 10, Exceptional, (36)
"Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! "
Mindi Z.
$248 nightly
The price is $287
Dec 14 - Dec 15
Total with taxes and fees
Vacation Home in Monona
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!9.8 out of 10, Exceptional, (47)
"We had a great time on our weekend trip to Madison. Location was super quick to get to downtown, house was clean, and we really enjoyed taking the canoe out on the lakes to explore."
Molly S.
$439 nightly
The price is $498
Dec 14 - Dec 15
Total with taxes and fees
Vacation Home in Fitchburg
Snowy Madison Escape | Warm Executive Home10.0 out of 10, Exceptional, (19)
"Property was generally clean, spacious and had all the amenities that our family needed.An enjoyable stay at a nice property!"
Kim & Jeff T.
$696 nightly
The price is $783
Dec 14 - Dec 15
Total with taxes and fees
Vacation Home in Downtown Madison
One Bedroom King with views of the heart of downtown.10.0 out of 10, Exceptional, (2)
"The property was easy to check-in and very clean! It had all the amenities to feel right at home. Excellent location close to restaurants within walking distance. We had a lovely time!"
Vikki T.
$205 nightly
The price is $237
Dec 14 - Dec 15
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.
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Top Rutland Hotel Reviews
Hampton Inn & Suites Madison / Downtown
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 | $783 |
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