Deals on vacations and trips to Madison
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Madison flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Clarion Pointe Charlottesville
The Meadows
Price was $438, price is now $392 per person
$392
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
This hotel doesn't skimp on freebies - guests receive free self-serve breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a 24-hour gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort
Price was $498, price is now $418 per person
$418
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
2 outdoor pools, a hot tub, and a gym are all featured at this hotel. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
Inn and Tavern at Meander
Price was $770, price is now $652 per person
$652
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
A restaurant, free self parking, and a terrace are among this bed & breakfast's amenities. WiFi in public areas is free. A garden, a snack bar/deli, and a lobby fireplace are also on offer.
Comfort Inn & Suites Orange - Montpelier
Price was $467, price is now $414 per person
$414
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Lafayette Inn
Price was $593, price is now $543 per person
$543
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A terrace, concierge services, and wedding services are also on offer.
Top Madison hotels deals
The Cabin at the Lake
Madison VA
$263 nightly
The price is $290 total per night
$290 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This cabin featured laundry facilities and barbecue grills.
Kitchen
Washer
Massanutten Resort
1822 Resort Dr McGaheysville VA
$132 nightly
The price is $146 total per night
$146 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a golf course, a full-service spa, and a water park. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy snowboarding. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities.
Pool
Hot Tub
English Inn of Charlottesville
2000 Morton Drive Charlottesville VA
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $109 total per night
$109 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Hampton Inn Charlottesville
2035 India Rd Charlottesville VA
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $102 total per night
$102 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a seasonal outdoor pool on site, and a 24-hour front desk and a snack bar/deli are also provided.
Pool
Breakfast included
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
1600 Emmet Street Charlottesville VA
Free Cancellation
$93 nightly
The price is $106 total per night
$106 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
DoubleTree by Hilton Hotel Charlottesville
990 Hilton Heights Rd Charlottesville VA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $107 total per night
$107 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.
Pool
Free airport shuttle
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.
Popular places to visit
Early Mountain Vineyards
4.5/5(19 reviews)
You can enjoy a tasting or tour at Early Mountain Vineyards during your travels to Madison. Discover the mountain views and wineries in this relaxing area.
Madison Plaza
You can enjoy retail therapy at Madison Plaza during your stay in Madison. You can seek out the hiking trails in this family-friendly area.
Lawrence Beasley Park
Explore the great outdoors at Lawrence Beasley Park, a lovely green space in Madison. You can seek out the hiking trails in this family-friendly area.
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