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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.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $447, price is now $393 per person
$393
per person
Nov 12 - Nov 15
found 14 hours ago
Roundtrip flight included
PBI (PBI) to Hartford (BDL)
Book a stay at this business-friendly hotel in Southington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lake Compounce and Panthorn Park are located nearby.

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $960, price is now $756 per person
$756
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Chicago (MDW) 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.
Good buffet

Reviewed on Aug 17, 2026

Two Trees Inn

Two Trees Inn

2.5 out of 5
Price was $724, price is now $590 per person
$590
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) 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.

Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $764, price is now $623 per person
$623
per person
Oct 30 - Nov 1
found 1 day 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.

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $647, price is now $552 per person
$552
per person
Nov 4 - Nov 8
found 8 hours ago
Roundtrip flight included
Minneapolis (MSP) 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 Lake Compounce and Crystal Bees are located nearby.
Clean room. Breakfast was good especially the biscuits

Reviewed on Aug 19, 2026

The Cromwell Inn

The Cromwell Inn

2.5 out of 5
Price was $553, price is now $483 per person
$483
per person
Nov 4 - Nov 8
found 8 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
I stayed at this property a few times staff very helpful and polite good thing they have breakfast again its a decent place to stay at

Reviewed on Aug 7, 2026

Homewood Suites by Hilton Southington, CT

Homewood Suites by Hilton Southington, CT

3 out of 5
Price was $552, price is now $486 per person
$486
per person
Nov 12 - Nov 15
found 14 hours ago
Roundtrip flight included
PBI (PBI) to Hartford (BDL)
Stay at this hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lake Compounce and Crystal Bees are located nearby.

Howard Johnson by Wyndham Hartford South – Rocky Hill

Howard Johnson by Wyndham Hartford South – Rocky Hill

2 out of 5
Price was $549, price is now $486 per person
$486
per person
Nov 4 - Nov 8
found 8 hours ago
Roundtrip flight included
Minneapolis (MSP) to Hartford (BDL)
Book a stay at this business-friendly 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 Mill Woods Park and Rocky Hill - Glastonbury Ferry are located nearby.

Middletown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Motel 6 Enfield, CT - Hartford

Motel 6 Enfield, CT - Hartford

2 out of 5
Price was $456, price is now $388 per person
$388
per person
Oct 22 - Oct 25
found 12 hours ago
Roundtrip flight included
Minneapolis (MSP) to Hartford (BDL)
Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $1,452, price is now $1,178 per person
$1,178
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip flight included
Minneapolis (MSP) to Hartford (BDL)
Two Trees Inn

Two Trees Inn

2.5 out of 5
Price was $724, price is now $590 per person
$590
per person
Oct 1 - Oct 4
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 $1,000, price is now $862 per person
$862
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Hartford (BDL)

Middletown Vacation Packages 5-7 Night Stays

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

Comfort Inn Griswold

2.5 out of 5
Price was $927, price is now $863 per person
$863
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Hartford (BDL)
Two Trees Inn

Two Trees Inn

2.5 out of 5
Price was $1,023, price is now $895 per person
$895
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Hartford (BDL)
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
Price was $1,011, price is now $885 per person
$885
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Hartford (BDL)
Great Wolf Lodge Mashantucket

Great Wolf Lodge Mashantucket

2 out of 5
Price was $1,297, price is now $1,221 per person
$1,221
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 4 days ago
$130
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Bradley Intl., returning Fri, Sep 11, priced at $130 found 4 days ago
Avelo Airlines
Fri, Aug 28 - Sun, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$149 Roundtrip, found 6 days ago
$149
Roundtrip
found 6 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 6 days ago
Frontier Airlines
Mon, Oct 12 - Fri, Oct 23
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$173 Roundtrip, found 3 hours ago
$173
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Oct 12 from Luis Munoz Marin Intl. to Bradley Intl., returning Fri, Oct 23, priced at $173 found 3 hours ago
American Airlines
Wed, Oct 21 - Wed, Oct 28
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day 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 1 day ago