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Madison Holiday Rentals

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Holiday Rentals in Madison

Historic Madison Eagle Inn

10.0 out of 10, Exceptional, (7)
"Loved the location, we were in town for a Wedding at Reinback Barn. Very clean and loved the bed and linens!"
The price is HK$1,374
HK$2,334 total
includes taxes & fees
10 Jul - 11 Jul
Historic Madison Eagle Inn

Spacious Retreat with Outdoor Firepit & Large Deck

9.6 out of 10, Exceptional, (27)
"This is a super nice place that is spacious, clean and comfortable.I would highly recommend!"
The price is HK$1,272
HK$2,217 total
includes taxes & fees
14 Jul - 15 Jul
Spacious Retreat with Outdoor Firepit & Large Deck

4BR Retreat Near Wineries, Weddings & Hiking

10.0 out of 10, Exceptional, (32)
"Stephen makes everyone feel welcome and comfortable in his beautiful house. Great comfy beds, amazing back yard and great breakfasts. I have already booked for next year!"
The price is HK$2,355
HK$4,625 total
includes taxes & fees
15 Jul - 16 Jul
4BR Retreat Near Wineries, Weddings & Hiking

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

9.8 out of 10, Exceptional, (86)
"Great place that works well for Rixey Manor weddings "
The price is HK$1,609
HK$3,315 total
includes taxes & fees
14 Jul - 15 Jul
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

9.4 out of 10, Exceptional, (32)
"Beautiful working farm and just the right size for an overnight stay before visiting Carter Mountain. The food recos were great, and the staff was welcoming and friendly."
The price is HK$1,727
HK$2,089 total
includes taxes & fees
15 Jul - 16 Jul
Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.

9.6 out of 10, Exceptional, (36)
"Outstanding stay!"
The price is HK$1,256
HK$1,524 total
includes taxes & fees
13 Jul - 14 Jul
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.

Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm

9.6 out of 10, Exceptional, (29)
"Had a wonderful time and highly recommend staying. "
The price is HK$3,140
HK$3,799 total
includes taxes & fees
14 Jul - 15 Jul
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm

The Ranch at Wine Country - Complimentary Bottle!

10.0 out of 10, Exceptional, (42)
"Our stay at The Ranch was a brief and quick one but it was a fantastic one! It was a last minute decision and one of the best we could have ever made. The hosts were phenomenal to work with in giving detail instructions for check in and check out. They also gave suggestions for the area as well. The house was beautiful and is as advertised. Had everything we needed for our one night stay. Would definitely recommend to anyone and hope to come back for a long stay ourselves!"
The price is HK$2,080
HK$3,529 total
includes taxes & fees
10 Jul - 11 Jul
The Ranch at Wine Country - Complimentary Bottle!

“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

10.0 out of 10, Exceptional, (32)
"Beautiful, serene location for the perfect weekend getaway! "
The price is HK$1,759
HK$2,544 total
includes taxes & fees
10 Jul - 11 Jul
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

Fern Cottage Summary:

10.0 out of 10, Exceptional, (13)
"We were all very comfortable in this wonderful home."
The price is HK$2,528
HK$4,803 total
includes taxes & fees
5 Aug - 6 Aug
Fern Cottage Summary:

Charming Private Suite in Historic Colonial House – right beside from The Inn!

10.0 out of 10, Exceptional, (14)
"an excellent option if dining at the INN"
The price is HK$1,099
HK$1,828 total
includes taxes & fees
4 Aug - 5 Aug
Charming Private Suite in Historic Colonial House – right beside from The Inn!

Colonial 3BR Home • Walk to The Inn • Great Location • Fast Wi-Fi

10.0 out of 10, Exceptional, (119)
"The house was comfy and well appointed. The owners have made every effort to cover whatever you might need while staying in the home. "
The price is HK$1,570
HK$2,505 total
includes taxes & fees
4 Aug - 5 Aug
Colonial 3BR Home • Walk to The Inn • Great Location • Fast Wi-Fi

Mint Cottage at Little Washington - a modern, spacious retreat with a view

10.0 out of 10, Exceptional, (6)
"Mint Cottage is a gem. Its spacious, beautifully furnished, and a great place to stay to explore Shenandoah National Park and its environs"
The price is HK$2,995
HK$3,644 total
includes taxes & fees
13 Jul - 14 Jul
Mint Cottage at Little Washington - a modern, spacious retreat with a view

Barn Apartment on Farm Near Old Rag and Shenandoah National Park

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay on the farm. Check in was easy, Jen was very accommodating and a wealth of information about the hikes and other things to do in the area."
The price is HK$848
HK$1,368 total
includes taxes & fees
31 Jul - 1 Aug
Barn Apartment on Farm Near Old Rag and Shenandoah National Park

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

10.0 out of 10, Exceptional, (3)
"Loved it, clean and as described, great farm."
The price is HK$636
HK$874 total
includes taxes & fees
10 Jul - 11 Jul
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

9.4 out of 10, Exceptional, (69)
"Nice place to stay for hiking."
The price is HK$3,497
HK$5,693 total
includes taxes & fees
14 Jul - 15 Jul
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

Tranquil Hazel River Cabin – Perfect for Relaxation & Exploration. Pet Friendly

The price is HK$1,876
HK$3,569 total
includes taxes & fees
15 Jul - 16 Jul
Tranquil Hazel River Cabin – Perfect for Relaxation & Exploration. Pet Friendly

Walk to Old Rag* hot tub* 360 mountain views

10.0 out of 10, Exceptional, (20)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
The price is HK$2,286
HK$4,963 total
includes taxes & fees
10 Jul - 11 Jul
Walk to Old Rag* hot tub* 360 mountain views

Charming Family Getaway Near Wineries & Skyline Drive; Sleeps 4; Short Stays OK

10.0 out of 10, Exceptional, (12)
"Easy check in and great description. Good location near Shenandoah National Park."
The price is HK$785
HK$1,521 total
includes taxes & fees
10 Jul - 11 Jul
Charming Family Getaway Near Wineries & Skyline Drive; Sleeps 4; Short Stays OK

Dream Dome - Romantic Retreat + Wifi A/C + Hot Tub

2.0 star property
10.0 out of 10, Exceptional, (2)
"This was a great place to stay for a change of setting. So much more fun than a hotel room. The hot tub was a nice extra and bed was super comfortable. Nice to be able to have a cup of coffee and sit outside at picnic table. Great place!"
The price is HK$2,267
HK$2,715 total
includes taxes & fees
22 Jul - 23 Jul
Dream Dome - Romantic Retreat + Wifi A/C + Hot Tub
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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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?

Mountainside Villas at Massanutten by Tripforth: This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Amenities such as kitchenware and free parking are also available for your convenience. You and your friends and family can relax into your holiday with amenities such as an outdoor tennis court. Another good choice for your trip to Madison is Old Rag View Horse Farm with Log Lodge and Treehouse.

How many holiday rentals will I find in Madison?

With 18 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 Lawrence Beasley Park.

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.