A calm body of water reflecting a sunset sky with scattered clouds.

Middleton Vacation Rentals

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Check prices for these dates

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

Our top choices for Middleton vacation rentals

An outdoor patio with a brick grill and seating area.

1. 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 SAR 502
SAR 661 total
includes taxes & fees
1 Nov - 2 Nov
King Suite | Free Breakfast. Pool and Hot Tub
A spacious living area with a wooden floor, a round mirror on the wall, and a dark-colored sofa.

2. Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Middleton
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place, great stay."
United States
Thomas D.
The price is SAR 578
SAR 1,079 total
includes taxes & fees
25 Oct - 26 Oct
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
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, (195 reviews)
"Good location"
United States
ANCA
The price is SAR 460
SAR 531 total
includes taxes & fees
1 Nov - 2 Nov
The Dylin
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

4. 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 SAR 297
SAR 472 total
includes taxes & fees
21 Oct - 22 Oct
A Room with a View
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

5. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is SAR 598
SAR 764 total
includes taxes & fees
13 Nov - 14 Nov
Pool with Slide. Great for Business Travelers!
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

6. The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Mount Horeb
9.8 out of 10, Exceptional, (33 reviews)
"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."
United States
Mike G.
The price is SAR 488
SAR 946 total
includes taxes & fees
21 Oct - 22 Oct
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
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 SAR 678
SAR 881 total
includes taxes & fees
25 Oct - 26 Oct
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A modern living room with a sofa, coffee table, and dining area.

8. Historic Luxury 2-bedroom apartment in Cross Plains, WI

Historic Luxury 2-bedroom apartment in Cross Plains, WI
Cross Plains
The price is SAR 845
SAR 1,577 total
includes taxes & fees
15 Oct - 16 Oct
Historic Luxury 2-bedroom apartment in Cross Plains, WI
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

9. Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two
Dane
10.0 out of 10, Exceptional, (3 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is SAR 556
SAR 934 total
includes taxes & fees
17 Oct - 18 Oct
Escape to tranquility – your countryside haven, and at times with a horse or two
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

10. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
The price is SAR 451
SAR 1,174 total
includes taxes & fees
13 Nov - 14 Nov
Studio Apartment at Cannery Square
A modern kitchen with a dishwasher, a dining area with a table and chairs, a living room with a sofa and a TV, and a ceiling fan.

11. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (30 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is SAR 477
SAR 1,327 total
includes taxes & fees
28 Oct - 29 Oct
2 Bed, 2 Bath Apartment at Cannery Square
A lobby with a wall displaying vintage advertisements, a sofa, a potted plant, and a window with blinds.

12. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (56 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
The price is SAR 477
SAR 1,335 total
includes taxes & fees
19 Oct - 20 Oct
2 Bed, 2 Bath Apartment at Cannery Square
Bright, open lobby seating area — a comfortable space to relax or catch up on work

13. 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 SAR 940
SAR 1,261 total
includes taxes & fees
13 Nov - 14 Nov
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A gym with treadmills, elliptical machines, and free weights.

14. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very good, (16 reviews)
"Great little town to stay the night. Woke early 5:30 am to tow truck towing cars in front lot. We luckily parked in back lot as instructed. Other than the noise of this unfortunate event, we enjoyed our stay. Loved the town and many places to walk to. Pizza place was amazing!"
United States
Cheryl B.
The price is SAR 477
SAR 1,077 total
includes taxes & fees
13 Nov - 14 Nov
Studio Apartment at Cannery Square
A modern kitchen with a refrigerator, microwave, and bar stools.

15. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (41 reviews)
"The host was very responsive and very kind and considerate to our reason for traveling. The property was beautiful and clean inside and out, we really enjoyed our stay."
United States
Sha'Vonne G.
The price is SAR 725
SAR 1,530 total
includes taxes & fees
15 Oct - 16 Oct
2 Bedroom Apartment Downtown Sun Prairie!
A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

16. 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 SAR 473
SAR 1,038 total
includes taxes & fees
1 Nov - 2 Nov
Charming Downtown Two Bedroom w/ Fireplace
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

17. 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 SAR 532
SAR 1,699 total
includes taxes & fees
1 Nov - 2 Nov
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A kitchen with a sliding glass door leading to a wooden deck with a view of a grassy field and a lake.

18. Updated home with lake views, across the street from Lake WI, near free ferry

Updated home with lake views, across the street from Lake WI, near free ferry
Merrimac
10.0 out of 10, Exceptional, (47 reviews)
"Very clean property, exactly as advertised. Host was easy to work with."
United States
Jacob M.
The price is SAR 672
SAR 1,272 total
includes taxes & fees
15 Oct - 16 Oct
Updated home with lake views, across the street from Lake WI, near free ferry
A chalkboard sign with a welcome message and room instructions.

19. Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Sun Prairie
10.0 out of 10, Exceptional, (24 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
The price is SAR 1,314
SAR 2,244 total
includes taxes & fees
12 Nov - 13 Nov
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
A spacious dining area with a high ceiling and large windows, wooden furniture, and a view of the outdoors.

20. Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.6 out of 10, Exceptional, (30 reviews)
"Great Place Beautiful landscape from the deckHost was very responsive Would go back again in a heartbeat Everything you need for a great stay"
United States
John W.
The price is SAR 620
SAR 1,419 total
includes taxes & fees
27 Oct - 28 Oct
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
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 Middleton 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 6 hours ago
The Madison Concourse Hotel and Governor's Club

Frequently asked questions

Can I find a vacation rental in Middleton?

Yes, we offer vacation rentals close to popular points of interest in Middleton, or you can go with a more secluded option if you want a relaxing place to stay. Tourists like the array of shops and top-notch restaurants in Middleton. Make sure you have time to check out the cafes and football games during your trip.

What's the top vacation rental that Middleton has to offer?

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail: Visitors like this Middleton 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.

How many vacation rentals are there in Middleton?

Choose from 4 Expedia vacation rentals in Middleton for a memorable vacation.

What’s there to see and do in Middleton?

Cultural attractions include National Mustard Museum, whereas Lake Mendota is a spot to enjoy nature. Other places in town to visit include Capital Brewery and Pheasant Branch Conservancy.

What’s a vacation rental in Middleton like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Middleton. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for families.