Holiday Rentals in Rutland

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Holiday Rentals in Rutland

The Dylin by Mint House

4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (119)
"Great location and very comfortable stay. Love the extra space to hang out."
United States
Brian
The price is €102
includes taxes & fees
23 Dec - 24 Dec
The Dylin by Mint House

220’ WATERFRONT BEACH ROCK RIVER WI PETS PIER POOL FP KYAKS FISHNG BOAT INCLUDED

Edgerton
9.8 out of 10, Exceptional, (168)
"The owners were great and super responsive. Wonderful property and location. "
United States
Michael R.
220’ WATERFRONT BEACH ROCK RIVER WI PETS PIER POOL FP KYAKS FISHNG BOAT INCLUDED

Conveniently Located just off University Avenue on Madison's West Side

Spring Harbor
10.0 out of 10, Exceptional, (131)
"It was great!"
United States
Guitar string S.
Conveniently Located just off University Avenue on Madison's West Side

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

Verona
9.6 out of 10, Exceptional, (69)
"Beautiful location, nice spacious and clean spot. We had a great time. "
United States
Sarah B.
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

ONE OF A KIND vacation rental with a view

Madison
10.0 out of 10, Exceptional, (147)
"This is a unique home that is super clean and had everything needed to cook, entertain (we played games & watched football) and accommodate any family. The location was close to downtown, the interstate, and airport. Plenty of restaurants were nearby as well. We thoroughly enjoyed our stay and would absolutely stay again. "
United States
Connie C.
ONE OF A KIND vacation rental with a view

Doty ★ Walk to Everything -Hotel Quality- Downtown

Downtown Madison
9.8 out of 10, Exceptional, (36)
"Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! "
United States
Mindi Z.
The price is €256
includes taxes & fees
14 Dec - 15 Dec
Doty ★ Walk to Everything -Hotel Quality- Downtown

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Faircrest
10.0 out of 10, Exceptional, (119)
"Scenic property, super zen, lovely hosts!"
United States
Christina C.
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Pool with Slide. Great for Business Travelers!

Fitchburg
The price is €142
includes taxes & fees
14 Dec - 15 Dec
Pool with Slide. Great for Business Travelers!

Log Cabin at Lake Koshkonong - “The Overlook”

Edgerton
9.2 out of 10, Wonderful, (47)
"Checkin was super easy, great amenities, and cozy cabin atmosphere."
United States
Nicholas R.
The price is €143
includes taxes & fees
7 Dec - 8 Dec
Log Cabin at Lake Koshkonong - “The Overlook”

Madison & ~UW~-Madison Area Lakefront Home

McFarland
10.0 out of 10, Exceptional, (202)
"What a lovely place to spend a few days with family! There was so much to do within a short distance but we loved being able to just chill on the water. We had a wonderful stay and can’t wait to visit again. Would highly recommend! "
United States
Jody G.
Madison & ~UW~-Madison Area Lakefront Home

Free Breakfast Pool & Hot Tub. Near UW-Madison

Madison
10.0 out of 10, Exceptional, (1)
"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 €264
includes taxes & fees
7 Dec - 8 Dec
Free Breakfast Pool & Hot Tub. Near UW-Madison

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

Monona
9.8 out of 10, Exceptional, (47)
"Such a nice house! Great location and excellent amenities!"
United States
Carson M.
The price is €441
includes taxes & fees
15 Dec - 16 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.

McFarland
10.0 out of 10, Exceptional, (12)
"Nice stay"
United States
Rebecca S.
Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.

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

Deerfield
10.0 out of 10, Exceptional, (133)
"Clean, quiet neighborhood, and plenty of space for our whole crew during Ironman weekend. Would recommend for anyone visiting the Madison area. "
United States
Alex T.
Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison

One Bedroom King with views of Lake Monona in the heart of downtown.

2.0 star property
Downtown Madison
The price is €220
includes taxes & fees
4 Jan - 5 Jan 2026
One Bedroom King with views of Lake Monona in the heart of downtown.

Clean and spacioius flat in great location near Epic and downtown Verona!

Verona
10.0 out of 10, Exceptional, (30)
"good location and value for the money. We were pleased to bring our dog with us!"
United States
audrey w.
Clean and spacioius flat in great location near Epic and downtown Verona!

On the Yahara River, access to Madison Lakes

Monona
10.0 out of 10, Exceptional, (52)
"Great stay - very relaxing!"
United States
Karen S.
On the Yahara River, access to Madison Lakes

Paoli Den - Renovated Flat!

Verona
9.8 out of 10, Exceptional, (31)
"Charming place, great communication with owners!"
United States
Ed D.
Paoli Den - Renovated Flat!

King Suite | Free Breakfast. Pool and Hot Tub

Middleton
8.0 out of 10, Very good, (5)
"Great place for a stay."
United States
Andy D.
The price is €125
includes taxes & fees
7 Dec - 8 Dec
King Suite | Free Breakfast. Pool and Hot Tub

Waterfront - Hot Tub - Sauna - Game Room - Pets

Edgerton
8.8 out of 10, Excellent, (5)
"Great place. Well outfitted and clean. Easy communication. No complaints and would return when in area."
United States
Mark W.
The price is €624
includes taxes & fees
7 Dec - 8 Dec
Waterfront - Hot Tub - Sauna - Game Room - Pets
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

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 €102 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?

220’ WATERFRONT BEACH ROCK RIVER WI PETS PIER POOL FP KYAKS FISHNG BOAT INCLUDED: 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 Olbrich Botanical Gardens. Stoughton Opera House and Alliant Energy Center 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.