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Windsor Vacation Packages

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Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $790, price is now $642 per person
$642
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Springfield (VSF)
Stay at this B&B in West Dover. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $1,232, price is now $955 per person
$955
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,145, price is now $956 per person
$956
per person
Jun 1 - Jun 6
found 14 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Quechee Gorge Bridge and Billings Park and Trail are located nearby.
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
Price was $1,181, price is now $990 per person
$990
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,616, price is now $1,397 per person
$1,397
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
Price was $1,341, price is now $1,192 per person
$1,192
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $985, price is now $888 per person
$888
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Colonel Williams Inn

Colonel Williams Inn

3 out of 5
Price was $1,034, price is now $939 per person
$939
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Springfield (VSF)
Stay at this B&B in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Southern Vermont Natural History Museum and Hogback Mountain Conservation Area are located nearby.

Windsor Vacation Packages 3-4 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 $783, price is now $756 per person
$756
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)

Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $790, price is now $642 per person
$642
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Springfield (VSF)
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $1,232, price is now $955 per person
$955
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,145, price is now $956 per person
$956
per person
Jun 1 - Jun 6
found 14 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Springfield (VSF)
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
Price was $1,181, price is now $990 per person
$990
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Springfield (VSF)

Top Flight Deals

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

Cape Air
Sat, May 30 - Wed, Jun 10
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 2 hours ago
$180
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 10, priced at $180 found 2 hours ago
Cape Air
Thu, May 28 - Mon, Jun 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 16 hours ago
$184
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 8, priced at $184 found 16 hours ago
Cape Air
Sat, May 30 - Wed, Jun 10
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$186 Roundtrip, found 2 hours ago
$186
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 10, priced at $186 found 2 hours ago
JetBlue Airways
Sat, May 30 - Wed, Jun 10
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 2 hours ago
$196
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 10, priced at $196 found 2 hours ago