Photo by Phil Martin

Madison Holiday Rentals

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Holiday Rentals in Madison

Massanutten's Woodstone Meadows by Tripforth

4.0 star property
9.0 out of 10, Wonderful, (190)
"Need luggage carts to load up going to different floors"
Massanutten's Woodstone Meadows by Tripforth

Mountainside Villas at Massanutten by Tripforth

3.5 star property
9.0 out of 10, Wonderful, (269)
"Price was fair and enough room for our family"
Mountainside Villas at Massanutten by Tripforth

Massanutten Resort by Tripforth

3.0 star property
7.8 out of 10, Good, (145)
"Beautiful area! Check in took us over a hour. Not enough details on the rental information "
Massanutten Resort by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4.0 star property
7.6 out of 10, Good, (124)
"The unit is in need of an update. The unit itself was difficult to find. Need better signage. If stairs is a problem this is not the unit for you"
Massanuttens Shenandoah Villas by Tripforth

The Summit at Massanutten Resort by Tripforth

3.5 star property
9.2 out of 10, Wonderful, (49)
"Will stay again "
The Summit at Massanutten Resort by Tripforth
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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Other types of properties in Madison you may be interested in

English Inn of Charlottesville

3.0 star property
9.2 out of 10, Wonderful, (1931)
"Great place to stay "
The price is S$129
includes taxes & fees
1 Dec - 2 Dec
English Inn of Charlottesville

Massanutten Resort

2.5 star property
8.0 out of 10, Very good, (546)
"Great stay for access to JMU Little pricey but over all good. Units should have more blankets available "
The price is S$165
includes taxes & fees
19 Dec - 20 Dec
Massanutten Resort

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

3.0 star property
9.0 out of 10, Wonderful, (1019)
"Friendly staff. Great pool area, the girls loved swimming every day. "
The price is S$147
includes taxes & fees
11 Dec - 12 Dec
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Madison?

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

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

Massanutten Resort by Tripforth: This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, an arcade/games room and free WiFi to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Madison?

With 20 Expedia holiday rentals, you're guaranteed to find just the right place for your Madison stay.

What can I see and do in Madison?

Shenandoah National Park and Rapidan River are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Early Mountain Vineyards and Sweely Estate Winery.

What are holiday rentals like in Madison?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Madison. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.