Search Deals onHinsdale Vacation Packages
Hinsdale Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
Price was $608, price is now $535 per person
$535
per person
Jan 20 - Jan 23
found 5 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.
Beautiful property set in a fantastic town. Proprietors were super nice and the property was absolutely beautiful. Would 100% recommend staying here.
Reviewed on Oct 24, 2026
The Shire Woodstock
Price was $1,055, price is now $925 per person
$925
per person
Dec 7 - Dec 11
found 6 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.
The Vesper
Price was $1,093, price is now $983 per person
$983
per person
Dec 7 - Dec 11
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Not very comfortable , broken or in need of repair toilet holder , mold in some grout in tub , road noise , not enough towels provided. For the price we paid it should have been more equipped cold oatmeal , not a hot breakfast
Reviewed on Oct 19, 2026
Jackson Gore Village, A Vail Resorts Property
Price was $1,015, price is now $919 per person
$919
per person
Dec 7 - Dec 11
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
The Covered Bridge Inn
Price was $652, price is now $593 per person
$593
per person
Dec 6 - Dec 8
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Good location. About what one might expect in a budget motel.
Reviewed on Oct 20, 2026
Winterplace at Okemo, A Vail Resorts Property
Price was $1,244, price is now $1,161 per person
$1,161
per person
Dec 7 - Dec 11
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Galaxy Bowl are located nearby.
Large unit - well laid out for three generation visit. Comfortable beds. Kitchen well appointed.
Reviewed on Oct 20, 2026
Solitude Village at Okemo by Vail Resorts
Price was $1,220, price is now $1,140 per person
$1,140
per person
Dec 7 - Dec 11
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Galaxy Bowl are located nearby.
Deer Brook Inn
Price was $1,153, price is now $1,082 per person
$1,082
per person
Dec 7 - Dec 11
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and climate control. Popular attractions Ottaquechee River and Union Arena Community Center are located nearby.
I highly recommend Deer Brook Inn. The photos don’t do it justice. It’s beautiful, cozy, well-kept and everything you’d want for a Vermont getaway. The innkeepers may be some of my favorite humans I’ve ever met. Their energy is bright and peaceful which reflects into the energy of the inn. They have cookies, coffee, teas and other drinks at night and a delicious custom breakfast in the morning. They have chickens out back, a fire pit and a sauna. It’s about a 7min drive from downtown Woodstock. Don't hesitate to book!
Reviewed on Oct 17, 2026
Hinsdale Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Hinsdale 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.
Fri, Nov 13 - Tue, Nov 17
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$273 Roundtrip, found 2 hours ago
$273
Roundtrip
found 2 hours ago
Fri, Jan 8 - Mon, Jan 25
LAX
Los Angeles Intl.
BOS
Logan Intl.
$286 Roundtrip, just found
$286
Roundtrip
just found
Wed, Nov 18 - Sat, Dec 5
PDX
Portland Intl.
ALB
Albany Intl.
$307 Roundtrip, found 2 hours ago
$307
Roundtrip
found 2 hours ago
Wed, Nov 18 - Thu, Nov 26
PDX
Portland Intl.
BOS
Logan Intl.
$330 Roundtrip, just found
$330
Roundtrip
just found
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