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Rutland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (195 reviews)
"Good location"
United States
ANCA
The price is ￥17,091
￥19,740 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥31,688
￥62,975 total
includes taxes & fees
Oct 19 - Oct 20
Spacious 3-bedroom apartment in Downtown Stoughton
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

3. 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 ￥12,541
￥19,913 total
includes taxes & fees
Oct 21 - Oct 22
A Room with a View
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

4. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is ￥25,216
￥32,755 total
includes taxes & fees
Oct 18 - Oct 19
Pool with Slide. Great for Business Travelers!
A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

5. 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 ￥19,989
￥43,826 total
includes taxes & fees
Nov 1 - Nov 2
Charming Downtown Two Bedroom w/ Fireplace
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.

6. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (14 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 ￥31,059
￥114,818 total
includes taxes & fees
Oct 15 - Oct 16
Lake Cabin | Sauna · River · Game Room
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

7. 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 ￥28,655
￥37,206 total
includes taxes & fees
Nov 11 - Nov 12
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A small cabin with a wooden deck and a glass door.

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

Log Cabin at Lake Koshkonong - “The Overlook”
Edgerton
9.2 out of 10, Wonderful, (53 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.
Log Cabin at Lake Koshkonong - “The Overlook”
An outdoor patio with a brick grill and seating area.

9. 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 ￥22,890
￥30,064 total
includes taxes & fees
Nov 12 - Nov 13
King Suite | Free Breakfast. Pool and Hot Tub
A library with wooden bookshelves, a staircase, and a chandelier.

10. 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 ￥19,719
￥43,858 total
includes taxes & fees
Nov 8 - Nov 9
Spacious Condo: Historic Boutique Rental in Downtown Edgerton
A dining area with a table set for four, a sofa, and a television mounted on the wall.

11. 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 ￥24,672
￥109,471 total
includes taxes & fees
Oct 20 - Oct 21
FirePit/Grill/PacMan Your Fall Escape Starts Here
A cozy living room with a sofa, coffee table, and large windows offering a view of trees.

12. Blue Lakeview Home

Blue Lakeview Home
Edgerton
The price is ￥21,416
￥42,512 total
includes taxes & fees
Nov 11 - Nov 12
Blue Lakeview Home
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

13. 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)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
The price is ￥22,421
￥71,815 total
includes taxes & fees
Nov 2 - Nov 3
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Bright, open lobby seating area — a comfortable space to relax or catch up on work

14. 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 ￥32,067
￥43,197 total
includes taxes & fees
Nov 1 - Nov 2
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Outdoor dining

15. 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)
The price is ￥25,065
￥52,887 total
includes taxes & fees
Oct 26 - Oct 27
Vast Lake Koshkonong Views from Pier, Deck, & Home
A spacious kitchen with wooden beams, a central island, and a dining area with a blue sofa and chairs.

16. 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 ￥60,600
￥90,148 total
includes taxes & fees
Oct 18 - Oct 19
Doty ★ Walk to Everything -Hotel Quality- Downtown
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.

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

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
Madison
The price is ￥54,133
￥73,081 total
includes taxes & fees
Nov 1 - Nov 2
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
A modern building with a dark wooden exterior, large windows, and a concrete entrance.

18. 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 ￥110,937
￥188,169 total
includes taxes & fees
Oct 15 - Oct 16
The Overhang · Luxury River Retreat with Sauna, Hot Tub, Movie Theater, & Arcade
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.

19. 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 ￥54,133
￥73,081 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥32,067
￥41,365 total
includes taxes & fees
Nov 1 - Nov 2
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

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"The bar staff upstairs in the governers lounge and downstairs in circle bar are fantastic"
Joseph 1-night trip
Posted less than an hour ago
The Madison Concourse Hotel and Governor's Club

Find out more about Rutland

Search for holiday rentals in Rutland on Expedia! You can easily find your home rentals, villas, holiday apartments in Rutland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Rutland!

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.