Compare Middleton Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Middleton Rentals

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

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

1.19 mi from city center
Guests staying at this vacation home enjoy an outdoor pool, laundry facilities, and local meal delivery service. Additional amenities include barbecue grills and a garden.
Pool
Kitchen
The Dylin by Mint House

The Dylin by Mint House

4 out of 5
611 E Dayton St, Madison, WI
6.37 mi from city center
$139 nightly
The price is $160 total per night
$160 total
Oct 5 - Oct 6
Total with taxes and fees
Guests of The Dylin by Mint House enjoy features like a 24-hour gym, free WiFi in public areas, and express check-out. Self parking is offered for USD 30 per night.
Kitchen
Washer
Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown

6.22 mi from city center
$485 nightly
The price is $561 total per night
$561 total
Oct 5 - Oct 6
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
ONE OF A KIND vacation rental with a view

ONE OF A KIND vacation rental with a view

5.71 mi from city center
Guests staying at this vacation home enjoy a water park, a sauna, and laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!

5.97 mi from city center
$168 nightly
The price is $189 total per night
$189 total
Oct 2 - Oct 3
Total with taxes and fees
At this apartment, guests have access to an indoor pool, laundry facilities, and barbecue grills.
Pool
Breakfast included
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

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

9.02 mi from city center
At this vacation home, guests enjoy an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly vacation home include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub
Private Pool - HOT TUB - Sauna - Game Room - Pets

Private Pool - HOT TUB - Sauna - Game Room - Pets

14.54 mi from city center
$975 nightly
The price is $1,055 total per night
$1,055 total
Oct 1 - Oct 2
Total with taxes and fees
Guests staying at this vacation home enjoy access to a water park, a gym, and a hot tub. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and a garden.
Pool
Hot Tub
Lake Wisconsin Resort

Lake Wisconsin Resort

3 out of 5
W10941 Corning St, Poynette, WI
20.08 mi from city center
Lake Wisconsin Resort features free WiFi in public areas and barbecue grills. You can take advantage of free parking if you drive. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. This cottage also has a picnic area.
Kitchen
Pet friendly
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

21.07 mi from city center
Guests staying at this cottage enjoy a water park, a hot tub, and barbecue grills. This smoke-free cottage also has a garden.
Hot Tub
Kitchen
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

22.02 mi from city center
Guests of this vacation home have access to an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly vacation home include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

22.12 mi from city center
Guests staying at this vacation home enjoy an indoor pool, a gym, and a sauna. Additional amenities include an arcade/game room, laundry facilities, and a garden.
Pool
Kitchen
Rocky Glen Condo - forest nest on Baraboo bluff

Rocky Glen Condo - forest nest on Baraboo bluff

23.08 mi from city center
$297 nightly
The price is $334 total per night
$334 total
Oct 1 - Oct 2
Total with taxes and fees
At this condo, guests have access to features like laundry facilities. This golf condo building also has a garden.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Middleton
View all properties
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.

Middleton Large Group Rentals

How to Book Vacation Rentals in Middleton



🏠 What is the best price for Middleton vacation rentals?

Middleton vacation rentals range in price, starting at $160 per night.


🏠 What types of vacation rentals in Middleton can I rent?

Orbitz offers a wide range of Middleton rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Middleton condo rentals.


🏠 Is it free to cancel my Middleton vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Middleton vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Middleton. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Middleton?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Middleton apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Middleton?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Middleton package deals will get you even more savings.

More to Explore

More to Explore