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

Latchis Hotel
Price was $487, price is now $409 per person
$409
per person
Jan 27 - Jan 30
found 1 day ago
Roundtrip 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 21 hours 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

Sinclair Inn Bed and Breakfast
Price was $607, price is now $527 per person
$527
per person
Jan 20 - Jan 23
found 22 hours 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 Veterans' Park and Mills Riverside Park are located nearby.

The Shire Woodstock
Price was $712, price is now $633 per person
$633
per person
Jan 2 - Jan 4
found 15 hours ago
Roundtrip flight included
Charlotte (CLT) 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.

Austrian Haus Lodge
Price was $546, price is now $489 per person
$489
per person
Jan 27 - Jan 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Stay at this hotel in West Dover. Enjoy free breakfast, free parking, and a sauna. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
I did not use it
Reviewed on Mar 20, 2026

Vikings Villages Resort
Price was $843, price is now $755 per person
$755
per person
Dec 27 - Dec 29
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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 Keets Brook Road Conservation Area are located nearby.
Viking Village is perfect in every way! If you're looking for a relaxed retreat, trails, nature, and delightfully detailed cabins and buildings, this is your dream stay. As you drive up toward the gates a sense of anticipation builds until the stockade fence and gate comes into view. It truly looks like you've traveled back in time once you arrive. Every cabin is slightly different. A raised walkway was thoughtfully built along the fronts of the cabins so you can avoid any snow or dirt as you come and go. Check-in is quick and Christina also gave us recommendations of nearby places to see or dine. The kitchenette does have what you'd need to cook and eat with for 4 people. Cabins are immaculate. Beds were comfortable. We made it a point to go out for the morning and evening feeding of the sheep. They may have been my favorite part of the stay! especially the lambs! We stayed 2 nights and enjoyed chatting with other guests around the firepit in the evening. (Their kids absolutely LOVED this place.) My husband and I are in our sixties and found the trails a little challenging! Quite hilly, but well marked. A heartfelt thank you to the folks running the Village. You were gracious hosts and made this someplace that we want to return to again! (Easier to get to than Iceland!)
Reviewed on Nov 7, 2026

The Vesper
Price was $1,098, price is now $985 per person
$985
per person
Dec 17 - Dec 21
found 12 hours 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

Hampton Inn Brattleboro
Price was $467, price is now $423 per person
$423
per person
Jan 27 - Jan 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. 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.
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
Price found within the past 48 hours. Click for updated prices.



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 3 days ago
$555
Roundtrip
found 3 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 3 days ago
$575
Roundtrip
found 3 days ago
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