Photo by Phil Martin

Search Holiday Homes in Madison

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Browse Select Madison Holiday Homes

Historic Madison Eagle Inn
Exterior detail

Historic Madison Eagle Inn

10.0 out of 10, Exceptional, (8)
"The place was great! It was clean and comfortable - a great jumping off point for a weekend of hiking in Shenandoah. Would definitely stay again. "
The price is £244
includes taxes & fees
25 Aug - 26 Aug
Historic Madison Eagle Inn
4BR Retreat Near Wineries, Weddings & Hiking
Fridge, microwave, oven, stovetop

4BR Retreat Near Wineries, Weddings & Hiking

10.0 out of 10, Exceptional, (32)
"We really enjoyed our stay. Family and friends stayed at Culpeper for my daughter's wedding. The house is warm, friendly and very inviting. Highly recommended! spacious. and Thank you! "
4BR Retreat Near Wineries, Weddings & Hiking
Newly renovated entire guest suite in Orange County.
Property grounds

Newly renovated entire guest suite in Orange County.

10.0 out of 10, Exceptional, (43)
"Myla was such a wonderful hostess. She shared cucumbers from her garden with us. This place was like a home away from home. Cozy and had everything you need. We stayed here 5 nights. My dog loved trying to hunt the squirrels. And the flowers smelled amazing when you stepped outside every morning. I highly recommend staying here. "
Newly renovated entire guest suite in Orange County.
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Property grounds

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

9.8 out of 10, Exceptional, (87)
"Great place that works well for Rixey Manor weddings "
The price is £304
includes taxes & fees
9 Sept - 10 Sept
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.
Outdoor dining

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 £201
includes taxes & fees
24 Aug - 25 Aug
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.
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (36)
"Outstanding stay!"
The price is £148
includes taxes & fees
17 Aug - 18 Aug
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Terrace/patio

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 £364
includes taxes & fees
18 Aug - 19 Aug
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
The Ranch at Wine Country - Complimentary Bottle!
Interior

The Ranch at Wine Country - Complimentary Bottle!

10.0 out of 10, Exceptional, (42)
"We had a wedding at a local winery and this was the perfect venue for our group. Had a great time. The host was incredibly accommodating and was flexible with check in so we could have time to get ready. Only thing is the ladies wished there was a full length mirror for getting ready. Otherwise no complaints. "
The price is £338
includes taxes & fees
18 Aug - 19 Aug
The Ranch at Wine Country - Complimentary Bottle!
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Exterior

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

10.0 out of 10, Exceptional, (33)
"Beautiful, serene location for the perfect weekend getaway! "
The price is £244
includes taxes & fees
17 Aug - 18 Aug
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Charming Private Suite in Historic Colonial House – right beside from The Inn!
Exterior

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

10.0 out of 10, Exceptional, (15)
"an excellent option if dining at the INN"
The price is £162
includes taxes & fees
2 Sept - 3 Sept
Charming Private Suite in Historic Colonial House – right beside from The Inn!
Colonial 3BR Home • Walk to The Inn • Great Location • Fast Wi-Fi
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (119)
"Awesome house for a weekend getaway."
The price is £226
includes taxes & fees
15 Sept - 16 Sept
Colonial 3BR Home • Walk to The Inn • Great Location • Fast Wi-Fi
Mint Cottage at Little Washington - a modern, spacious retreat with a view
Terrace/patio

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 £452
includes taxes & fees
28 Aug - 29 Aug
Mint Cottage at Little Washington - a modern, spacious retreat with a view
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Exterior

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

9.6 out of 10, Exceptional, (4)
"Loved it, clean and as described, great farm."
The price is £85
includes taxes & fees
19 Aug - 20 Aug
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
TV, fireplace, video games, DVD player

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

9.4 out of 10, Exceptional, (70)
"Nice place to stay for hiking."
The price is £523
includes taxes & fees
17 Aug - 18 Aug
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
Walk to Old Rag* hot tub* 360 mountain views
Smart TV, ping pong, books

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 £468
includes taxes & fees
3 Sept - 4 Sept
Walk to Old Rag* hot tub* 360 mountain views
Charming Family Getaway Near Wineries & Skyline Drive; Sleeps 4; Short Stays OK
Exterior

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

10.0 out of 10, Exceptional, (13)
"Easy check in and great description. Good location near Shenandoah National Park."
The price is £145
includes taxes & fees
18 Aug - 19 Aug
Charming Family Getaway Near Wineries & Skyline Drive; Sleeps 4; Short Stays OK
Dream Dome - Romantic Retreat + Wifi A/C + Hot Tub
Fridge, microwave, oven, stovetop

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"The Dream Dome was such a great experience. Had everything we needed and very close to Shenandoah NP"
Dream Dome - Romantic Retreat + Wifi A/C + Hot Tub
Zen Dome - Romantic Retreat + Wifi A/C + Hot Tub
Fridge, microwave, oven, stovetop

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

2.0 star property
The price is £318
includes taxes & fees
11 Sept - 12 Sept
Zen Dome - Romantic Retreat + Wifi A/C + Hot Tub
Ridgeview Mountain Cabin
Fireplace, DVD player

Ridgeview Mountain Cabin

9.4 out of 10, Exceptional, (42)
"This was the perfect little cabin for me and my husband. The location was perfect for us. We went to the Laray Caverns and hiked Old Rag. The owner was very helpful and has great communication! Planning another trip soon! "
The price is £276
includes taxes & fees
20 Aug - 21 Aug
Ridgeview Mountain Cabin
Overlook Mountain Cabin
Outdoor dining

Overlook Mountain Cabin

9.8 out of 10, Exceptional, (160)
"Beautiful mountain view! The trip was nice and beautiful! I love a good cozy vibe in the mountains! Communication with property manger was very excellent customer service! "
The price is £281
includes taxes & fees
14 Sept - 15 Sept
Overlook Mountain Cabin
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

English Inn of Charlottesville

English Inn of Charlottesville

10/10 Excellent
"Great place!"
Chad 2-night trip
Posted 1 day ago
English Inn of Charlottesville