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Rockingham Vacation Packages

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Rockingham Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Windham Hill Inn

Windham Hill Inn

4 out of 5
Price was $554, price is now $459 per person
$459
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this B&B in West Townshend. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hot Glass Works and Ball Mountain State Park are located nearby.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $986, price is now $845 per person
$845
per person
Aug 22 - Aug 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Mills Riverside Park and Waters Memorial Library are located nearby.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Price was $599, price is now $535 per person
$535
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Four Columns Inn

Four Columns Inn

4 out of 5
Price was $586, price is now $525 per person
$525
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Stay at this B&B in Newfane. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Moore Free Library and Rock River Preserve are located nearby.
Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts

4 out of 5
Price was $547, price is now $491 per person
$491
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $553, price is now $499 per person
$499
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park are located nearby.
Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $1,381, price is now $1,266 per person
$1,266
per person
Jul 26 - Jul 30
found 2 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this luxury guesthouse in Bolton Landing. Enjoy free WiFi, a full-service spa, and room service. Popular attractions Lake George and Adirondack Extreme Adventure Course are located nearby.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,102, price is now $1,016 per person
$1,016
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Middle Covered Bridge are located nearby.

Rockingham Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $553, price is now $499 per person
$499
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $1,381, price is now $1,266 per person
$1,266
per person
Jul 26 - Jul 30
found 2 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Inn at Valley Farms

Inn at Valley Farms

2 out of 5
Price was $876, price is now $820 per person
$820
per person
Jul 24 - Jul 28
found 2 hours ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)

Rockingham Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $986, price is now $845 per person
$845
per person
Aug 22 - Aug 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)

Top Flight Deals

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

JetBlue Airways
Mon, Sep 21 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$502 Roundtrip, found 3 days ago
$502
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Sep 21 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $502 found 3 days ago
United
Fri, Sep 11 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$509 Roundtrip, found 3 days ago
$509
Roundtrip
found 3 days ago
Select United flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $509 found 3 days ago
JetBlue Airways
Mon, Sep 21 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$512 Roundtrip, found 5 days ago
$512
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Sep 21 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $512 found 5 days ago
United
Wed, Sep 23 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$745 Roundtrip, found 4 days ago
$745
Roundtrip
found 4 days ago
Select United flight, departing Wed, Sep 23 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $745 found 4 days ago