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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.
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2 out of 5
Price was $322, price is now $256 per person
$256
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free breakfast, free WiFi, and free parking. 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.

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $381, price is now $286 per person
$286
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

The Cromwell Inn

The Cromwell Inn

2.5 out of 5
Price was $390, price is now $303 per person
$303
per person
Dec 3 - Dec 7
found 11 hours ago
Roundtrip flight included
Orlando (MCO) 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 Putter's Paradise Mini Golf are located nearby.

Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Save 100% on your flight
Price was $670, price is now $522 per person
$522
per person
Dec 3 - Dec 7
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

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
Price was $1,462, price is now $1,141 per person
$1,141
per person
Nov 11 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this business-friendly hotel in Montville. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mohegan Sun Casino and Mohegan Sun Arena are located nearby.

Two Trees Inn

Two Trees Inn

2.5 out of 5
Price was $1,103, price is now $875 per person
$875
per person
Nov 11 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.

Grantmoore Motor Lodge

Grantmoore Motor Lodge

2 out of 5
Save 100% on your flight
Price was $13,409, price is now $10,698 per person
$10,698
per person
Nov 10 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Hartford (BDL)
Stay at this motel in Newington. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Iwo Jima Survivors Memorial Park and New Britain Stadium are located nearby.
No es lo q ofrecen no lo recomiendo

Reviewed on Jun 14, 2026

Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

2.5 out of 5
Price was $880, price is now $706 per person
$706
per person
Nov 11 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.

Middletown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $381, price is now $286 per person
$286
per person
Dec 3 - Dec 7
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 $1,118, price is now $818 per person
$818
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
The Cromwell Inn

The Cromwell Inn

2.5 out of 5
Price was $390, price is now $303 per person
$303
per person
Dec 3 - Dec 7
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Save 100% on your flight
Price was $670, price is now $522 per person
$522
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)

Middletown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $767, price is now $669 per person
$669
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 $945, price is now $766 per person
$766
per person
Oct 27 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $3,177, price is now $2,668 per person
$2,668
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Two Trees Inn

Two Trees Inn

2.5 out of 5
Price was $847, price is now $745 per person
$745
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop 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
Fri, Dec 4 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$82 Roundtrip, found 12 hours ago
$82
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Orlando Intl. to Bradley Intl., returning Sat, Dec 12, priced at $82 found 12 hours ago
Frontier Airlines
Wed, Oct 14 - Fri, Oct 23
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 3 days ago
$161
Roundtrip
found 3 days 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 3 days ago
Breeze Airways
Thu, Oct 22 - Sun, Nov 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$170 Roundtrip, found 4 hours ago
$170
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Thu, Oct 22 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Nov 8, priced at $170 found 4 hours ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$179 Roundtrip, found 3 days ago
$179
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 $179 found 3 days ago