Holiday Rentals in Rutland

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Rutland

Our top choices for Rutland holiday rentals

The Dylin by Mint House

4.0 star property
9.2 out of 10, Wonderful, (86)
"Nice, clean, well-equipped and well-decorated rooms. "
The Dylin by Mint House

YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS

9.8 out of 10, Exceptional, (163)
"Great spot for a large group of family and friends. Very comfortable size, nice porch/yard and great layout."
YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS

Log Cabin at Lake Koshkonong - “The Overlook”

9.4 out of 10, Exceptional, (39)
"It was very comfortable, clean, and well equipped. The balcony on the second floor was really nice. Kitchen was a great size for the cabin."
The price is €172
includes taxes & fees
23 Sept - 24 Sept
Log Cabin at Lake Koshkonong - “The Overlook”

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (33)
"Had a great stay!"
Doty ★ Walk to Everything -Hotel Quality- Downtown

Pool with Slide. Great for Business Travelers!

The price is €163
includes taxes & fees
1 Sept - 2 Sept
Pool with Slide. Great for Business Travelers!

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (141)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (64)
"The property was beautiful and our group of 8 had tons of space. It was beautiful and we wish we could’ve stayed longer. We would definitely stay there again. "
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Remodeled home with pontoon rental 2 decks Private beach playground volleyball

10.0 out of 10, Exceptional, (4)
"Very nice place. The beds and blankets were so comfortable. "
Remodeled home with pontoon rental 2 decks Private beach playground volleyball

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (24)
"Prefect"
Paoli Den - Newly Remodeled!

Waterfront - Hot Tub - Sauna - Game Room - Pets

9.0 out of 10, Wonderful, (4)
"Great place. Well outfitted and clean. Easy communication. No complaints and would return when in area."
Waterfront - Hot Tub - Sauna - Game Room - Pets

Spacious Condo: Historic Boutique Rental in Downtown Edgerton

2.0 star property
10.0 out of 10, Exceptional, (4)
"The feel was exactly what we were looking for! Great and very helpful staff!! Highly recommend and will more than likely stay again!!"
Spacious Condo: Historic Boutique Rental in Downtown Edgerton

Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison

10.0 out of 10, Exceptional, (130)
"Clean, quiet neighborhood, and plenty of space for our whole crew during Ironman weekend. Would recommend for anyone visiting the Madison area. "
Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (42)
"We enjoyed our stay!"
The price is €494
includes taxes & fees
10 Sept - 11 Sept
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Madison & ~UW~-Madison Area Lakefront Home

10.0 out of 10, Exceptional, (195)
"The cottage is a great location, hiking trail, restaurants and pubs in walking distance, and short drive to Madison. It is well-furnished, comfortable and is located on the water with great views. My friends and I would highly recommend this property."
Madison & ~UW~-Madison Area Lakefront Home

Boat Dock & Backyard: 'Rock River Retreat'

9.8 out of 10, Exceptional, (17)
"We enjoyed our stay! It was a lovely property."
Boat Dock & Backyard: 'Rock River Retreat'

Enjoy Nature with Full Comfort!

9.4 out of 10, Exceptional, (30)
"Great location, beautiful, clean, and friendly host"
The price is €113
includes taxes & fees
31 Aug - 1 Sept
Enjoy Nature with Full Comfort!

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

10.0 out of 10, Exceptional, (151)
"Fantastic area to explore"
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

Kosh Cottage - Beach Vibes & Kayak Rides!

2.0 star property
9.0 out of 10, Wonderful, (2)
"Adorable home perfect for our weekend away"
Kosh Cottage - Beach Vibes & Kayak Rides!

One Bedroom Queen in the heart of downtown.

2.0 star property
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 "
The price is €255
includes taxes & fees
1 Sept - 2 Sept
One Bedroom Queen in the heart of downtown.

Contemporary home in quiet neighborhood with pool & great back yard close to all

9.6 out of 10, Exceptional, (8)
"Everything was just as advertised. The backyard & stay was very enjoyable. Thank you for a lovely stay, Sheila!"
Contemporary home in quiet neighborhood with pool & great back yard close to all
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Rutland Hotel Reviews

Find out more about Rutland

Find out more about Rutland

Everything you need to know about Rutland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rutland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Rutland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rutland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rutland holiday rentals we have selected for you start as low as €113 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Rutland rentals

At Expedia, we put the best Rutland holiday 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 holiday.

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 holiday rentals in Rutland?

Yes, there are holiday rentals close to the most popular sights in Rutland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Rutland has to offer?

YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS: This holiday home rental outside of Rutland is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 University of Wisconsin-Madison Arboretum. Alliant Energy Center and Ho-Chunk Gaming Madison are a couple of places you'll find in the wider area.

What are holiday rentals like in Rutland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Rutland. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip.