Rutland Vacation Rentals from $135: Search Short-Term Rentals

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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

Downtown Madison

ANCA

$122 nightly

Nov 1 - Nov 2

Total with taxes and fees

A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

2. A Room with a View

Verona

Ashley J.

$128 nightly

Nov 8 - Nov 9

Total with taxes and fees

A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

3. Charming Downtown Two Bedroom w/ Fireplace

New Glarus

Heather & Nick V.

$250 nightly

Oct 28 - Oct 29

Total with taxes and fees

A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

4. Pool with Slide. Great for Business Travelers!

Fitchburg

$189 nightly

Oct 25 - Oct 26

Total with taxes and fees

A two-story building with a brown roof, a wooden front door, and a window with the number 318.

5. Spacious 3-bedroom apartment in Downtown Stoughton

Stoughton

$347 nightly

Oct 27 - Oct 28

Total with taxes and fees

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

Fitchburg

$214 nightly

Oct 25 - Oct 26

Total with taxes and fees

A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

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

Village of Cottage Grove

Anakin F.

$400 nightly

Oct 22 - Oct 23

Total with taxes and fees

A cozy living room with a sofa, coffee table, and large windows offering a view of trees.

8. Blue Lakeview Home

Edgerton

$256 nightly

Oct 26 - Oct 27

Total with taxes and fees

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Top Rutland Hotel Reviews

Best Western Premier Park Hotel

10/10 Excellent

"I had several points during my stay where I needed help with planning short trips. The staff was extremely helpful."

Tru by Hilton Madison West, WI

10/10 Excellent

"The room, while not large, was well thought out. The shower was large and you could step right into it. There were safety bars in good locations and the shower faucet was easy to use and regulate. The sink had a nice amount of space around it. Ice could be gotten from an ice machine in the lobby. There was a water machine next to it so that you could fill your water bottle with ice then water. Breakfast was free with pancakes you could make yourself, scrambled eggs, sausage, bagels, and oatmeal. The desk staff was welcoming and helpful."

Valued Stay Madison

8/10 Good

"In reality, this is a solid 3 stars. Nothing stood out enough to make it a 4 or 5, but nothing was bad enough to warrant a 1 or 2. I officially clicked 4 stars because anything below 4 is seen as "bad" on a review site. Cleanliness: the toilet, shower, floor, linens, shower, desk, fridge, microwave were all clean. There was a spot of something on the bathroom wall (all the walls seem to have been painted within the last few years), but washing down all the walls seems like expecting a lot. Comfort: the heat/AC worked well, the bed was fairly comfortable, and the linens were soft enough. The pillows were great an numerous. Ambiance: there's nothing exciting to look at out the window. This is a utility hotel. Most nights were quiet but there seemed to be people slamming doors all night one night. I never felt unsafe or uncomfortable. Parking seemed tight, especially if I got in later, but I found a spot each night. I could not smell the garbage dump (mid-October weather probably helped). Breakfast: exactly what I would expect from this type of hotel if not for all the reviews praising it. In fairness, I only went on Thurs/Fri, and there just weren't a lot of appealing options for a light meal. I think there were more options on Saturday/Sunday, but I skipped breakfast those days. Overall: as a single person going to an event at the Alliant Energy Center, this was a great choice. I will almost certainly pick the same hotel next year. With family I'd pick some place nicer."

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.

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Check prices for these dates

Our top choices for Rutland vacation rentals

1. The Dylin

2. A Room with a View

3. Charming Downtown Two Bedroom w/ Fireplace

4. Pool with Slide. Great for Business Travelers!

5. Spacious 3-bedroom apartment in Downtown Stoughton

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

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

8. Blue Lakeview Home

9. Lake Cabin | Sauna · River · Game Room

10. FirePit/Grill/Arcade Your Fall Escape Starts Here

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

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

13. Charming 3-bedroom house on Madison's Eastside! Close to everything!

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

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

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

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

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

Find vacation rentals that suit your style

Top Rutland Hotel Reviews

Best Western Premier Park Hotel

DoubleTree by Hilton Madison East

AmericInn by Wyndham Madison West

Hampton Inn & Suites Madison-West

Tru by Hilton Madison West, WI

Baymont by Wyndham Madison West/Middleton WI West

Valued Stay Madison

Days Inn & Suites by Wyndham Madison

Cambria Hotel Madison East

Find out more about Rutland

Frequently asked questions

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