Search Deals onWindsor Vacation Packages
Windsor Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Latchis Hotel
Price was $631, price is now $501 per person
$501
per person
Dec 17 - Dec 21
found 15 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.

Lincoln Inn & Gallery
Price was $1,686, price is now $1,068 per person
$1,068
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this guesthouse in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.
The hotel was amazing and the staff was so kind. Luke was working the front desk and made sure we had everything we needed. The hotel and property are beautiful. We really enjoyed our time and can't wait to come back!
Reviewed on Nov 8, 2026

The Shire Woodstock
Price was $1,940, price is now $1,646 per person
$1,646
per person
Dec 23 - Dec 27
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Perfect stay in a beautiful town. Can't wait to come back.
Reviewed on Nov 11, 2026

1846 Inn and Tavern
Price was $935, price is now $810 per person
$810
per person
Dec 17 - Dec 21
found 15 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
The Inn also has an adjacent nice food tavern and music this weekend. Friendly host - embodied the helpful spirit of old inns. Helped with allowing a late dinner due to late arrival. Adjusted the heat for us and allowed us to set a bit extra in their library.
Very welcoming. A ++ for hospitality and making us welcome!
Reviewed on Oct 12, 2026

The Vesper
Price was $1,098, price is now $985 per person
$985
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Quechee Gorge Bridge and Billings Park and Trail are located nearby.
The staff… they were lovely. So helpful and delightful.
The room was perfect and met all my needs. Bed was comfy.
Breakfast was delicious.
Overall I had a wonderful stay. Quiet and peaceful atmosphere. Friendly staff.
Will definitely comeback.
Reviewed on Nov 10, 2026

Sinclair Inn Bed and Breakfast
Price was $795, price is now $713 per person
$713
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Veterans' Park and Mills Riverside Park are located nearby.

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Price was $923, price is now $835 per person
$835
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Good hotel. Spacious rooms. Offered many choices for breakfast. Gym was too small.
Reviewed on Nov 11, 2026

Deerhill Inn
Price was $1,153, price is now $1,062 per person
$1,062
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this B&B in West Dover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
I loved every second of my stay at Deerhill Inn and am officially converted to staying at inns! The Delphinium Room was spotless, comfortable, and so welcoming I wished I could move in. I loved the spacious bathroom with its black-and-white tile, the cozy fireplace, and even the wonderfully helpful instructions for using the tub and shower. Such a thoughtful little detail!
Breakfast was outstanding. Scott is a wonderful cook, and I especially loved the morning scones. He was also happy to make me simple scrambled eggs and toast instead of the more elaborate menu choices. Ariane was absolutely delightful, and sweet Josie the Schnauzer was the perfect finishing touch.
Beautiful inn, wonderful hosts, and so many thoughtful details. I can’t wait to come back!
Reviewed on Sep 28, 2026
Windsor Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Windsor Vacation Packages 5-7 Night Stays
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$555 Roundtrip, found 4 days ago
$555
Roundtrip
found 4 days ago

Thu, Nov 19 - Sat, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$565 Roundtrip, found 6 days ago
$565
Roundtrip
found 6 days ago

Thu, Nov 19 - Sat, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$570 Roundtrip, found 6 days ago
$570
Roundtrip
found 6 days ago

Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$575 Roundtrip, found 4 days ago
$575
Roundtrip
found 4 days ago
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