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Your Madison Vacation
History, cuisine, art and more … There's a whole lot to discover with a Madison vacation package. And with the ability to easily customize your city getaway, you know it'll be one that's tough to forget. Early Mountain Vineyards is just one of the must-see attractions to check off your to-do list during a trip to Madison. Your Madison vacation is just a few clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your travel style.
The Latest Madison vacation packages
Price found within the past 48 hours. Click for updated prices.

Microtel Inn & Suites by Wyndham Harrisonburg
Price was $306, price is now $259 per person
$259
per person
Jun 22 - Jun 25
found 23 hours ago
Roundtrip flight included
New York (NYC) to Weyers Cave (SHD)
8.4/10 Very Good! (1,008 reviews)
A bit noisy with doors and people coming and going.
Reviewed on May 4, 2026

The Blackburn Inn and Conference Center
Price was $384, price is now $318 per person
$318
per person
Jun 22 - Jun 25
found 23 hours ago
Roundtrip flight included
New York (NYC) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,013 reviews)
My room was spacious, great high ceilings, comfortable. It’s an old building, so creaky wood floors especially in bedroom. Beautiful bathroom, modern glass shower, great lighting, rainfall shower head. Great towels; cheap, thin, polyester linens on bed, good pillows. Bed average. Window coverings excellent for keeping light out, easily opened shades for super large windows.
TVs great, but very difficult to find channels because guide does not match on paper or on screen and the two tvs are different also.
Glass doors in hallways help with noise. AC great. But, I was awakened and only got about 5 hrs sleep second night because very loud guests, 1 male and 1 female, came in at 1:15-1:30 am and did not quiet down quickly.
I also was very disappointed by the pet policy—my std poodle was very good, but not being able to leave him in the room, and not knowing that until I checked in, was very difficult. I would not stay here again with a pet.
Also, it was the first time I visited this property (large property)and would have loved to have had front desk staff point out some of the things I should see. Never did see any restaurants or anything else. Was directed to parking and side door after asking a question.
Nicest staff member was young woman who brought me 2 bandaids when I got a small skin tear Wed. night (5/20) after shower.
Told front desk checking out bathroom needs touch up paint on windowsill.
Reviewed on May 21, 2026

Dinsmore Boutique Inn
Venable
Price was $934, price is now $774 per person
$774
per person
Jul 24 - Jul 26
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Charlottesville (CHO)
9.6/10 Exceptional! (383 reviews)
no elevator to 2nd floor room. clean, parking OK and good breakfast
Reviewed on May 16, 2026

Virginia Guesthouse Hotel
Lewis Mountain
Price was $839, price is now $714 per person
$714
per person
Jul 24 - Jul 26
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Charlottesville (CHO)
9/10 Wonderful! (14 reviews)
I would’ve given this hotel five stars, had I been charged their normal rack rates. It’s brand new, beautiful, and has an extremely friendly and professional staff. Unfortunately, at nearly $1000 per night on graduation weekend, it raises the expectations and the hotel does not meet that price category of property. It’s a clearly cashing in on a captive audience but seems to be a common theme in the area. That said, as long as you avoid the gauging times, this is an excellent hotel near UVA.
Reviewed on May 18, 2026

The Doyle Hotel
Starr Hill
Price was $812, price is now $696 per person
$696
per person
Jul 24 - Jul 26
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Charlottesville (CHO)
8.4/10 Very Good! (1,010 reviews)
The hotel is beautiful - sleek and chic! Great location and stellar staff. The rooftop bar and restaurant is my favorite place in Charlottesville. (The gluten-free pizza is FANTASTIC!). The rooms are nice, but there was mildew on the shower walls the last 2 times we stayed there. The gym has some broken equipment, but that won't stop us from coming back! The best value in the area.
Reviewed on May 8, 2026
What to do in Madison

Shenandoah National Park Self-Guided Driving Audio Tour
$17
per traveler
100% of travellers recommend
Madison Hotel Deals

The Cabin at the Lake
Madison VA
$260 nightly
The price is $286 total per night from May 25 to May 26
$286 total
May 25 - May 26
Total with taxes and fees
9.8/10 Exceptional! (50 reviews)
"Great view and access to the lake!"
Reviewed on May 11, 2026

English Inn of Charlottesville
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $123 total per night from May 26 to May 27
$123 total
May 26 - May 27
Total with taxes and fees
9.2/10 Wonderful! (2,834 reviews)
"It was a great place to stay during our visit."
Reviewed on May 21, 2026

Massanutten Resort
1822 Resort Dr McGaheysville VA
$119 nightly
The price is $131 total per night from May 26 to May 27
$131 total
May 26 - May 27
Total with taxes and fees
8/10 Very Good! (1,325 reviews)
"The property is set in a beautiful mountain setting with great amenities. The rooms are dated and well worn but it is a great value foe the area."
Reviewed on May 21, 2026
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.
Find the Best Madison Vacation Packages
Madison Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Charlottesville-Albemarle Airport (CHO) |
Population | 220 |
Max Temp Winter | 45ºF |
Max Temp Summer | 85ºF |
Top Sights | Early Mountain Vineyards and Rapidan Camp |
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