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Rutland Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Rutland vacation rentals

A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

1. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (191 reviews)
"I loved the apartment hotel concept. Felt very homey and had a kitchen which was wonderful. Location was in a quiet neighborhood and underground parking was wonderful. Also enjoyed the keyless check in process. Staff was very responsive."
United States
Andrea
The price is AED 576
AED 666 total
includes taxes & fees
19 Oct - 20 Oct
The Dylin
A two-story building with a brown roof, a wooden front door, and a window with the number 318.

2. Spacious 3-bedroom apartment in Downtown Stoughton

Spacious 3-bedroom apartment in Downtown Stoughton
Stoughton
The price is AED 749
AED 1,472 total
includes taxes & fees
20 Oct - 21 Oct
Spacious 3-bedroom apartment in Downtown Stoughton
A large, two-story log cabin with a stone chimney, a front porch with outdoor seating, and a snow-covered yard leading to a fire pit.

3. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (13 reviews)
"We love this property on the Sugar River. Very spacious, rustic but with all the modern amenities. Beautiful view of the water and lots of wildlife in area. "
United States
Lisa and Peter R.
The price is AED 719
AED 2,658 total
includes taxes & fees
8 Oct - 9 Oct
Lake Cabin | Sauna · River · Game Room
A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

4. Charming Downtown Two Bedroom w/ Fireplace

Charming Downtown Two Bedroom w/ Fireplace
New Glarus
10.0 out of 10, Exceptional, (28 reviews)
"Amazing location, nicely furnished and cozy!"
United States
Heather & Nick V.
The price is AED 496
AED 1,063 total
includes taxes & fees
2 Nov - 3 Nov
Charming Downtown Two Bedroom w/ Fireplace
A library with wooden bookshelves, a staircase, and a chandelier.

5. Spacious Condo: Historic Boutique Rental in Downtown Edgerton

Spacious Condo: Historic Boutique Rental in Downtown Edgerton
Edgerton
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful.. just beautiful and right at the hert if town"
United States
Georgia S.
The price is AED 485
AED 1,069 total
includes taxes & fees
20 Oct - 21 Oct
Spacious Condo: Historic Boutique Rental in Downtown Edgerton
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

6. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is AED 546
AED 711 total
includes taxes & fees
11 Oct - 12 Oct
Pool with Slide. Great for Business Travelers!
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

7. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (56 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
The price is AED 312
AED 484 total
includes taxes & fees
2 Nov - 3 Nov
A Room with a View
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

8. King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
The price is AED 624
AED 813 total
includes taxes & fees
11 Oct - 12 Oct
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

9. Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
9.8 out of 10, Exceptional, (19 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is AED 520
AED 1,658 total
includes taxes & fees
4 Nov - 5 Nov
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
An outdoor seating area with wicker furniture and a central fire feature.

10. Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Madison
10.0 out of 10, Exceptional, (1 review)
"Clean, quiet, and convenient! Everything went smooth."
United States
Thomas C.
The price is AED 742
AED 989 total
includes taxes & fees
1 Nov - 2 Nov
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A spacious kitchen with wooden beams, a central island, and a dining area with a blue sofa and chairs.

11. Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (46 reviews)
"Great place!"
United States
Robert F.
The price is AED 1,403
AED 2,007 total
includes taxes & fees
8 Oct - 9 Oct
Doty ★ Walk to Everything -Hotel Quality- Downtown
Outdoor dining

12. Vast Lake Koshkonong Views from Pier, Deck, & Home

Vast Lake Koshkonong Views from Pier, Deck, & Home
Edgerton
10.0 out of 10, Exceptional, (2 reviews)
Vast Lake Koshkonong Views from Pier, Deck, & Home
A dining area with a table set for four, a sofa, and a television mounted on the wall.

13. FirePit/Grill/PacMan Your Fall Escape Starts Here

FirePit/Grill/PacMan Your Fall Escape Starts Here
Milton
10.0 out of 10, Exceptional, (24 reviews)
"Clean, pet friendly and well appointed. Would be great to revisit in summer when we could enjoy all of the outdoor amenities. Highly recommend. "
United States
Vicky Z.
The price is AED 770
AED 2,774 total
includes taxes & fees
12 Oct - 13 Oct
FirePit/Grill/PacMan Your Fall Escape Starts Here
A small cabin with a wooden deck and a glass door.

14. Log Cabin at Lake Koshkonong - “The Overlook”

Log Cabin at Lake Koshkonong - “The Overlook”
Edgerton
9.2 out of 10, Wonderful, (52 reviews)
"Thank you for a peaceful stay, we came from Arizona to host my mothers memorial and the comfort and relaxation was well needed, plus it was big enough to have my kids spend time with us as well. Thank you for everything!"
United States
Kelly T.
The price is AED 477
AED 853 total
includes taxes & fees
13 Oct - 14 Oct
Log Cabin at Lake Koshkonong - “The Overlook”
An outdoor patio with a brick grill and seating area.

15. King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (6 reviews)
"Great place for a stay."
United States
Andy D.
The price is AED 491
AED 640 total
includes taxes & fees
1 Nov - 2 Nov
King Suite | Free Breakfast. Pool and Hot Tub
A modern two-story house with a large circular window on the left side, a smaller window on the right, and a door in the center.

16. The Overhang · Luxury River Retreat with Sauna, Hot Tub, Movie Theater, & Arcade

The Overhang · Luxury River Retreat with Sauna, Hot Tub, Movie Theater, & Arcade
Janesville
10.0 out of 10, Exceptional, (2 reviews)
"Another great stay at this beautiful home. The hosts are very responsive and supportive."
United States
R D.
The price is AED 2,569
AED 4,357 total
includes taxes & fees
8 Oct - 9 Oct
The Overhang · Luxury River Retreat with Sauna, Hot Tub, Movie Theater, & Arcade
A cozy living room with a sofa, coffee table, and large windows offering a view of trees.

17. Blue Lakeview Home

Blue Lakeview Home
Edgerton
The price is AED 777
AED 1,331 total
includes taxes & fees
20 Oct - 21 Oct
Blue Lakeview Home
A hotel room with a bed, a desk, a lamp, a framed picture, a kitchen area with cabinets and a microwave, and a carpeted floor.

18. Free Breakfast Pool & Hot Tub. Near East Towne Mall!

Free Breakfast Pool & Hot Tub. Near East Towne Mall!
Madison
10.0 out of 10, Exceptional, (1 review)
"It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well."
United States
Joy E.
The price is AED 1,253
AED 1,677 total
includes taxes & fees
1 Nov - 2 Nov
Free Breakfast Pool & Hot Tub. Near East Towne Mall!
A conference room with multiple tables and chairs, a projector screen, and a carpeted floor.

19. Free Breakfast. Pool & Hot Tub. Near East Towne Mall!

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
Madison
The price is AED 1,253
AED 1,677 total
includes taxes & fees
1 Nov - 2 Nov
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
A hotel room with a bed, a desk, a lamp, a framed picture, a kitchen area with cabinets and a microwave, and a carpeted floor.

20. Accessible 1BR Suite | Free Daily Breakfast & Pool

Accessible 1BR Suite | Free Daily Breakfast & Pool
Madison
The price is AED 742
AED 951 total
includes taxes & fees
1 Nov - 2 Nov
Accessible 1BR Suite | Free Daily Breakfast & Pool
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

DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

10/10 Excellent
"All staff were particularly helpful - front desk, restaurant and van drivers. Anxious to be sure my stay was exceptional."
John 3-night trip
Posted 3 hours ago
DoubleTree by Hilton Madison Downtown

Frequently asked questions

Are there vacation rentals in Rutland?

Yes, we have vacation rentals near top sights in Rutland, or you can go with a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental that Rutland has to offer?

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail: Visitors like this Rutland vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a selection of games, and a hot tub so you can immerse yourself in your vacation.

What can I see and do in Rutland?

While exploring the area, visit family-friendly sights like Henry Vilas Zoo, or get outside and enjoy nature at Olbrich Botanical Gardens. Stoughton Opera House and Alliant Energy Center are a couple of places you'll find in the larger area.

What are vacation rentals like in Rutland?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Rutland. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family getaway.