Search Deals on
Madison Vacation Packages

Build your package with 2 more options

Madison Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
Price was $504, price is now $409 per person
$409
per person
Jul 24 - Jul 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Price was $633, price is now $438 per person
$438
per person
Jul 24 - Jul 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Downtown Mall and John Paul Jones Arena are located nearby.
Kimpton The Forum Hotel by IHG

Kimpton The Forum Hotel by IHG

4 out of 5
Save 100% on your flight
Price was $1,278, price is now $976 per person
$976
per person
Sep 2 - Sep 6
found 18 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

3 out of 5
Save 100% on your flight
Price was $1,376, price is now $1,061 per person
$1,061
per person
Sep 2 - Sep 6
found 18 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
Stay at this hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions John Paul Jones Arena and Scott Stadium are located nearby.
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Price was $1,086, price is now $855 per person
$855
per person
Sep 2 - Sep 6
found 18 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
Book a stay at this business-friendly B&B in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Downtown Mall and John Paul Jones Arena are located nearby.
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Price was $654, price is now $520 per person
$520
per person
Jul 24 - Jul 27
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Price was $951, price is now $769 per person
$769
per person
Sep 2 - Sep 6
found 18 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
Stay at this hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a picnic area. Our guests praise the helpful staff in our reviews. Popular attractions Scott Stadium and John Paul Jones Arena are located nearby.
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

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

3 out of 5
Price was $514, price is now $421 per person
$421
per person
Jul 24 - Jul 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.

Madison Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $633, price is now $438 per person
$438
per person
Jul 24 - Jul 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Charlottesville (CHO)
Kimpton The Forum Hotel by IHG

Kimpton The Forum Hotel by IHG

4 out of 5
UVA
Save 100% on your flight
Price was $1,278, price is now $976 per person
$976
per person
Sep 2 - Sep 6
found 18 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

3 out of 5
Lewis Mountain
Save 100% on your flight
Price was $1,376, price is now $1,061 per person
$1,061
per person
Sep 2 - Sep 6
found 18 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $1,086, price is now $855 per person
$855
per person
Sep 2 - Sep 6
found 18 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)

Madison Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Inn At Warm Springs

The Inn At Warm Springs

3.5 out of 5
Price was $1,328, price is now $1,301 per person
$1,301
per person
Aug 9 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Weyers Cave (SHD)
The Anderson Cottage Bed & Breakfast

The Anderson Cottage Bed & Breakfast

3 out of 5
Price was $1,819, price is now $1,665 per person
$1,665
per person
Aug 9 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Weyers Cave (SHD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Tue, Sep 29 - Sat, Oct 3
ORD
O'Hare Intl.
SHD
Shenandoah Valley Regional
$234 Roundtrip, found 20 hours ago
$234
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Sep 29 from O'Hare Intl. to Shenandoah Valley Regional, returning Sat, Oct 3, priced at $234 found 20 hours ago
American Airlines
Tue, Aug 25 - Wed, Sep 2
IAH
George Bush Intercontinental
CHO
Charlottesville-Albemarle
$291 Roundtrip, found 5 days ago
$291
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Aug 25 from George Bush Intercontinental to Charlottesville-Albemarle, returning Wed, Sep 2, priced at $291 found 5 days ago
Delta
Tue, Aug 11 - Mon, Aug 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$296 Roundtrip, found 1 day ago
$296
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 11 from O'Hare Intl. to Charlottesville-Albemarle, returning Mon, Aug 17, priced at $296 found 1 day ago
Delta
Thu, Jul 9 - Tue, Jul 14
DFW
Dallas-Fort Worth Intl.
CHO
Charlottesville-Albemarle
$352 Roundtrip, found 1 day ago
$352
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jul 9 from Dallas-Fort Worth Intl. to Charlottesville-Albemarle, returning Tue, Jul 14, priced at $352 found 1 day ago