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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.
Inn on Storrs

Inn on Storrs

3.5 out of 5
Price was $627, price is now $477 per person
$477
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Book a stay at this business-friendly motel in Willimantic. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions East Brook Mall and Windham Recreation Park are located nearby.
Basic hotel - good for overnight stay

Reviewed on Sep 7, 2026

Delamar West Hartford

Delamar West Hartford

4 out of 5
Save 100% on your flight
Price was $1,131, price is now $864 per person
$864
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

Inn at Middletown

Inn at Middletown

3.5 out of 5
Price was $837, price is now $662 per person
$662
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Book a stay at this business-friendly hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions General Mansfield House and Harbor Park are located nearby.

Graduate by Hilton Storrs

Graduate by Hilton Storrs

4 out of 5
Price was $727, price is now $588 per person
$588
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

Landing Apartments Vernon

Landing Apartments Vernon

3.5 out of 5
Price was $1,100, price is now $892 per person
$892
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Book a stay at this family-friendly apartment in Vernon. Enjoy free parking, a fitness center, and a fireplace in the lobby. Popular attractions Shoppes at Buckland Hills and Promenade Shops at Evergreen Walk are located nearby.
Our stay was very good. Way better than staying at a hotel. Would definitely do it again.

Reviewed on Aug 9, 2026

Landing in Downtown Hartford Near Dunkin' Park

Landing in Downtown Hartford Near Dunkin' Park

3.5 out of 5
Price was $660, price is now $544 per person
$544
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 $773, price is now $640 per person
$640
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Clean, quiet, great restaurant and pub. Food was over the top delicious!

Reviewed on Sep 3, 2026

Trumbull Apartments

Trumbull Apartments

3 out of 5
Price was $623, price is now $525 per person
$525
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Stay at this apartment in Hartford. Enjoy laundry facilities, Netflix, and climate control. Popular attractions PeoplesBank Arena and The Meadows Music Theatre are located nearby.
Terrible, worst stay ever . It was such a hassle to get in no clear instructions… never again

Reviewed on Sep 1, 2026

Middletown Vacation Packages 3-4 Night Stays

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

Inn on Storrs

3.5 out of 5
Price was $627, price is now $477 per person
$477
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Delamar West Hartford

Delamar West Hartford

4 out of 5
Save 100% on your flight
Price was $1,131, price is now $864 per person
$864
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Inn at Middletown

Inn at Middletown

3.5 out of 5
Washington Street Historic District
Price was $837, price is now $662 per person
$662
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $901, price is now $717 per person
$717
per person
Oct 10 - Oct 13
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)

Middletown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Landing Apartments Vernon

Landing Apartments Vernon

3.5 out of 5
Price was $1,100, price is now $892 per person
$892
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Two Trees Inn

Two Trees Inn

2.5 out of 5
Price was $1,128, price is now $916 per person
$916
per person
Oct 17 - Oct 24
found 18 hours ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $3,027, price is now $2,540 per person
$2,540
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $1,186, price is now $997 per person
$997
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hartford (BDL)

Top Flight Deals

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

Frontier Airlines
Thu, Dec 3 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$82 Roundtrip, found 9 hours ago
$82
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Orlando Intl. to Bradley Intl., returning Sat, Dec 12, priced at $82 found 9 hours ago
Frontier Airlines
Wed, Oct 14 - Fri, Oct 23
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 19 hours ago
$161
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Luis Munoz Marin Intl. to Bradley Intl., returning Fri, Oct 23, priced at $161 found 19 hours ago
Breeze Airways
Thu, Dec 3 - Thu, Dec 3
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$168 Roundtrip, found 6 days ago
$168
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Dec 3, priced at $168 found 6 days ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$179 Roundtrip, found 19 hours ago
$179
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $179 found 19 hours ago