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Middletown Vacation Packages

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Middletown Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Solano Inn

Solano Inn

2.5 out of 5
Price was $391, price is now $298 per person
$298
per person
Oct 9 - Oct 12
found 2 hours ago
Roundtrip flight included
Jacksonville (JAX) to Hartford (BDL)
Stay at this hotel in Portland. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Arrigoni Winery and Chris Cote's Toptracer Golf Range and Performance Center are located nearby.
IT WAS IMMACULATE

Reviewed on Aug 16, 2026

Delamar West Hartford

Delamar West Hartford

4 out of 5
Save 100% on your flight
Price was $1,146, price is now $908 per person
$908
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) 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 The Meadows Music Theatre are located nearby.

Two Trees Inn

Two Trees Inn

2.5 out of 5
Price was $775, price is now $627 per person
$627
per person
Oct 23 - Oct 29
found 1 day 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.
It was ok. Some stains on the furniture cushion’s they should be replaced. Sinks don’t drain either. It was an OK stay.

Reviewed on Aug 17, 2026

Landing in Downtown Hartford Near Dunkin' Park

Landing in Downtown Hartford Near Dunkin' Park

3.5 out of 5
Price was $678, price is now $557 per person
$557
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Hartford (BDL)
Book a stay at this business-friendly apartment in Hartford. Enjoy free parking, an outdoor pool, and a fitness center. Popular attractions PeoplesBank Arena and The Meadows Music Theatre are located nearby.
It says parking is included but I had to pay for parking every day. Front desk couldn’t fix it, the people she called didn’t fix it. Missed a work meeting because of the whole ordeal. Just the night is $24.

Reviewed on May 3, 2026

Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $763, price is now $631 per person
$631
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) 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.

Graduate by Hilton Storrs

Graduate by Hilton Storrs

4 out of 5
Price was $997, price is now $826 per person
$826
per person
Oct 8 - Oct 11
found 20 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Hartford (BDL)
Stay at this hotel in Storrs. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harry A. Gampel Pavilion and Ballard Institute and Museum of Puppetry are located nearby.

Comfort Inn & Suites East Hartford - Hartford

Comfort Inn & Suites East Hartford - Hartford

2.5 out of 5
Price was $407, price is now $340 per person
$340
per person
Oct 9 - Oct 12
found 2 hours ago
Roundtrip flight included
Jacksonville (JAX) to Hartford (BDL)
Book a stay at this business-friendly hotel in East Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Meadows Music Theatre and PeoplesBank Arena are located nearby.
Clean room, easy to access

Reviewed on Aug 17, 2026

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $551, price is now $469 per person
$469
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) 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.
Great location. Great hot breakfast. Not just muffins and rolls.

Reviewed on Aug 17, 2026

Middletown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Solano Inn

Solano Inn

2.5 out of 5
Price was $391, price is now $298 per person
$298
per person
Oct 9 - Oct 12
found 2 hours ago
Roundtrip flight included
Jacksonville (JAX) to Hartford (BDL)
Delamar West Hartford

Delamar West Hartford

4 out of 5
Save 100% on your flight
Price was $1,146, price is now $908 per person
$908
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Hartford (BDL)
Landing in Downtown Hartford Near Dunkin' Park

Landing in Downtown Hartford Near Dunkin' Park

3.5 out of 5
Downtown Hartford
Price was $678, price is now $557 per person
$557
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Hartford (BDL)
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $763, price is now $631 per person
$631
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Hartford (BDL)

Middletown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

2.5 out of 5
Price was $648, price is now $512 per person
$512
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Hartford (BDL)
Hilton Garden Inn Hartford South/Glastonbury

Hilton Garden Inn Hartford South/Glastonbury

3 out of 5
Save 100% on your flight
Price was $1,072, price is now $836 per person
$836
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Hartford (BDL)
Two Trees Inn

Two Trees Inn

2.5 out of 5
Price was $775, price is now $627 per person
$627
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Hartford (BDL)
Motel 6 Enfield, CT - Hartford

Motel 6 Enfield, CT - Hartford

2 out of 5
Price was $720, price is now $594 per person
$594
per person
Sep 23 - Sep 29
found 11 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Hartford (BDL)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Thu, Sep 10 - Fri, Sep 11
MCO
Orlando Intl.
BDL
Bradley Intl.
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Bradley Intl., returning Fri, Sep 11, priced at $130 found 2 days ago
Avelo Airlines
Fri, Aug 28 - Sun, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$149 Roundtrip, found 3 days ago
$149
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Fri, Aug 28 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Sun, Aug 30, priced at $149 found 3 days ago
American Airlines
Wed, Oct 21 - Wed, Oct 28
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$177 Roundtrip, found 8 hours ago
$177
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Wed, Oct 21 from Ronald Reagan Washington National to Bradley Intl., returning Wed, Oct 28, priced at $177 found 8 hours ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$180 Roundtrip, found 3 days ago
$180
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $180 found 3 days ago