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Rutland Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Rutland vacation rentals

A small cabin with a wooden deck and a glass door.

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

Log Cabin at Lake Koshkonong - “The Overlook”
Edgerton
9.2 out of 10, Wonderful, (51 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.
$182 nightly
The price is $192
Sep 7 - Sep 8
Total with taxes and fees
Log Cabin at Lake Koshkonong - “The Overlook”
A library with wooden bookshelves, a staircase, and a chandelier.

2. 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.
$260 nightly
The price is $269
Sep 22 - Sep 23
Total with taxes and fees
Spacious Condo: Historic Boutique Rental in Downtown Edgerton
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

3. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (178 reviews)
"The freaking best place."
United States
Seth
$142 nightly
The price is $164
Sep 7 - Sep 8
Total with taxes and fees
The Dylin
A two-story building with a brown roof, a wooden front door, and a window with the number 318.

4. Spacious 3-bedroom apartment in Downtown Stoughton

Spacious 3-bedroom apartment in Downtown Stoughton
Stoughton
$322 nightly
The price is $365
Sep 14 - Sep 15
Total with taxes and fees
Spacious 3-bedroom apartment in Downtown Stoughton
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

5. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (54 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
$128 nightly
The price is $135
Sep 8 - Sep 9
Total with taxes and fees
A Room with a View
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
$160 nightly
The price is $181
Sep 10 - Sep 11
Total with taxes and fees
Pool with Slide. Great for Business Travelers!
An outdoor patio with a brick grill and seating area.

7. 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.
$152 nightly
The price is $173
Sep 7 - Sep 8
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
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
$194 nightly
The price is $220
Sep 7 - Sep 8
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

9. Charming Downtown Two Bedroom w/ Fireplace

Charming Downtown Two Bedroom w/ Fireplace
New Glarus
10.0 out of 10, Exceptional, (23 reviews)
"Amazing location, nicely furnished and cozy!"
United States
Heather & Nick V.
$262 nightly
The price is $290
Sep 30 - Oct 1
Total with taxes and fees
Charming Downtown Two Bedroom w/ Fireplace
A cozy living room with a sofa, coffee table, and large windows offering a view of trees.

10. Blue Lakeview Home

Blue Lakeview Home
Edgerton
$256 nightly
The price is $270
Sep 9 - Sep 10
Total with taxes and fees
Blue Lakeview Home
A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

11. 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, (56 reviews)
"Great little lake house, close to downtown Madison. "
United States
LiHsin C.
$457 nightly
The price is $519
Sep 14 - Sep 15
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

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

Vast Lake Koshkonong Views from Pier, Deck, & Home
Edgerton
$340 nightly
The price is $359
Sep 9 - Sep 10
Total with taxes and fees
Vast Lake Koshkonong Views from Pier, Deck, & Home
A spacious living room with a fireplace, a large TV mounted on a stone wall, and a dining area with a kitchen in the background.

13. Campus-Area 4BR | Panoramic Bluffs

Campus-Area 4BR | Panoramic Bluffs
Fitchburg
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful place with lots of room. "
United States
Brenda B.
$677 nightly
The price is $769
Sep 7 - Sep 8
Total with taxes and fees
Campus-Area 4BR | Panoramic Bluffs
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

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

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (16 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
$422 nightly
The price is $479
Oct 4 - Oct 5
Total with taxes and fees
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
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.

15. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (11 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.
$755 nightly
The price is $797
Sep 8 - Sep 9
Total with taxes and fees
Lake Cabin | Sauna · River · Game Room
A conference room with multiple tables and chairs, a projector screen, and a carpeted floor.

16. 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.
$211 nightly
The price is $244
Sep 7 - Sep 8
Total with taxes and fees
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A hotel pantry with a refrigerator stocked with beverages, a microwave, and shelves with snacks and condiments.

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

Accessible 1BR Suite | Free Daily Breakfast & Pool
Madison
$210 nightly
The price is $243
Sep 7 - Sep 8
Total with taxes and fees
Accessible 1BR Suite | Free Daily Breakfast & Pool
A hot tub with a view of a lake and trees.

18. Waterfront - Hot Tub - Sauna - Game Room - Pets

Waterfront - Hot Tub - Sauna - Game Room - Pets
Edgerton
9.0 out of 10, Wonderful, (11 reviews)
"This house was perfect for a weekend getaway with friends. Very spacious, lots of big beds, and perfect for the dogs as well. The hot tub and sauna were very refreshing. We'd definitely stay here again!"
United States
Tony
$883 nightly
The price is $974
Sep 23 - Sep 24
Total with taxes and fees
Waterfront - Hot Tub - Sauna - Game Room - Pets
A spacious kitchen with wooden beams, a central island, and a dining area with a blue sofa and chairs.

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

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (45 reviews)
"Great place!"
United States
Robert F.
$491 nightly
The price is $567
Sep 7 - Sep 8
Total with taxes and fees
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.

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

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
Madison
$301 nightly
The price is $349
Sep 7 - Sep 8
Total with taxes and fees
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
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
"Loved it."
Jason 2-night trip
Posted 3 hours ago
The Madison Concourse Hotel and Governor's Club

Find out more about Rutland

Everything you need to know about Rutland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rutland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rutland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rutland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rutland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Rutland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $135 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rutland rentals

At Expedia, we put the best Rutland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Rutland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rutland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rutland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.