Search Deals onMiddletown Vacation Packages
Middletown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Cromwell Inn
Price was $460, price is now $394 per person
$394
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this business-friendly hotel in Cromwell. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Cromwell Commons Shopping Center and Brownstone Exploration & Discovery Park are located nearby.
Delamar West Hartford
Price was $1,194, price is now $795 per person
$795
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this spa hotel in West Hartford. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions PeoplesBank Arena and Blue Back Square are located nearby.
Very clean and the staff was very friendly
Reviewed on Nov 10, 2026
Holiday Inn Express Vernon - Manchester by IHG
Price was $617, price is now $496 per person
$496
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.
Candlewood Suites Windsor Locks Bradley Arpt by IHG
Price was $492, price is now $406 per person
$406
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.
Staff was very helpful and accommodating,
Reviewed on Nov 10, 2026
Holiday Inn Express Southington by IHG
Price was $572, price is now $479 per person
$479
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Crystal Bees and Hawks Landing Country Club are located nearby.
Holiday Inn Express Hartford South - Rocky Hill by IHG
Price was $623, price is now $529 per person
$529
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this golf hotel in Rocky Hill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rocky Hill - Glastonbury Ferry and Dinosaur State Park are located nearby.
10/10
Reviewed on Nov 8, 2026
Hilton Garden Inn Hartford South/Glastonbury
Price was $633, price is now $542 per person
$542
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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 Glastonbury Historic District are located nearby.
Safe, comfortable and clean! Best place in the area to stay.
Reviewed on Nov 3, 2026
Holiday Inn Express & Suites Meriden by IHG
Price was $761, price is now $652 per person
$652
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this spa hotel in Meriden. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lamentation Mountain State Park and Silver Lake State Access Area 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.
Fri, Dec 11 - Sun, Dec 13
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$143 Roundtrip, found 9 hours ago
$143
Roundtrip
found 9 hours ago
Fri, Dec 11 - Sun, Dec 13
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$143 Roundtrip, found 2 hours ago
$143
Roundtrip
found 2 hours ago
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$143 Roundtrip, found 14 hours ago
$143
Roundtrip
found 14 hours ago
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$168 Roundtrip, found 4 hours ago
$168
Roundtrip
found 4 hours ago
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