Search Deals onMiddletown Vacation Packages
Middletown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Windsor Locks Bradley Arpt by IHG
Price was $648, price is now $512 per person
$512
per person
Oct 23 - Oct 29
found 10 hours ago
Roundtrip flight included
Chicago (MDW) to Hartford (BDL)
Book a stay at this family-friendly hotel in Windsor Locks. Enjoy free WiFi, free parking, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Connecticut Fallen Firefighters Memorial and New England Air Museum are located nearby.
Hilton Garden Inn Hartford South/Glastonbury
Save 100% on your flight
Price was $1,072, price is now $836 per person
$836
per person
Oct 23 - Oct 29
found 10 hours ago
Roundtrip flight included
Chicago (MDW) to Hartford (BDL)
Book a stay at this business-friendly hotel in Glastonbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions PeoplesBank Arena and The Meadows Music Theatre are located nearby.
Would not recommend.
Reviewed on Aug 15, 2026
Two Trees Inn
Price was $775, price is now $627 per person
$627
per person
Oct 23 - Oct 29
found 10 hours ago
Roundtrip flight included
Chicago (MDW) to Hartford (BDL)
Book a stay at this business-friendly hotel in Mashantucket. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Foxwoods Resort Casino and Grand Theater at Foxwoods Resort Casino are located nearby.
Sleep Inn & Suites Niantic North
Price was $735, price is now $606 per person
$606
per person
Sep 23 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Hartford (BDL)
Book a stay at this business-friendly hotel in Niantic. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Flanders Plaza Shopping Center and White Gate Farm are located nearby.
Great stat after visiting the Dinosaur Place!
Reviewed on Aug 15, 2026
Holiday Inn Express Vernon - Manchester by IHG
Price was $798, price is now $689 per person
$689
per person
Sep 25 - Sep 27
found 19 hours ago
Roundtrip flight included
Chicago (MDW) to Hartford (BDL)
Book a stay at this business-friendly hotel in Vernon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Shoppes at Buckland Hills and Cinemark Buckland Hills 18 are located nearby.
Grand Pequot Tower at Foxwoods
Price was $1,228, price is now $1,085 per person
$1,085
per person
Sep 23 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Hartford (BDL)
Book a stay at this spa hotel in Mashantucket. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Foxwoods Resort Casino and Grand Theater at Foxwoods Resort Casino are located nearby.
The indoor pool at Pequot was very clean and kids friendly. The are at least 2 arcades here that kept the kids entertained. Guy Fieri's restaurant has a kid's menu that was really good as well. All restaurant staff super friendly.
Reviewed on Aug 13, 2026
Avon Old Farms Hotel
Price was $777, price is now $688 per person
$688
per person
Sep 25 - Sep 27
found 19 hours ago
Roundtrip flight included
Chicago (MDW) to Hartford (BDL)
Book a stay at this family-friendly hotel in Avon. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Farmington River and Sperry Park are located nearby.
The Fox Tower at Foxwoods
Price was $1,164, price is now $1,031 per person
$1,031
per person
Sep 23 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Hartford (BDL)
Book a stay at this spa hotel in Mashantucket. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Foxwoods Resort Casino and Grand Theater at Foxwoods Resort Casino are located nearby.
Middletown Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Middletown 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.
Thu, Sep 10 - Fri, Sep 11
MCO
Orlando Intl.
BDL
Bradley Intl.
$130 Roundtrip, found 18 hours ago
$130
Roundtrip
found 18 hours ago
Fri, Aug 28 - Sun, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$149 Roundtrip, found 2 days ago
$149
Roundtrip
found 2 days ago
Sat, Sep 5 - Sat, Sep 12
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$177 Roundtrip, found 20 hours ago
$177
Roundtrip
found 20 hours ago
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$180 Roundtrip, found 2 days ago
$180
Roundtrip
found 2 days ago
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