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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 Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $390, price is now $325 per person
$325
per person
Sep 25 - Sep 28
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 Lake Compounce and Crystal Bees are located nearby.

Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Save 100% on your flight
Price was $663, price is now $504 per person
$504
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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 Farmington Valley Arts Center are located nearby.

Solano Inn

Solano Inn

2.5 out of 5
Price was $576, price is now $440 per person
$440
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.

Inn at Middletown

Inn at Middletown

3.5 out of 5
Save 100% on your flight
Price was $805, price is now $632 per person
$632
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.
The room was very clean

Reviewed on Jul 23, 2026

Landing Apartments West Windsor

Landing Apartments West Windsor

4 out of 5
Price was $645, price is now $511 per person
$511
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this golf apartment in Windsor. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Northwest Park and Wintonbury Hills Golf Course are located nearby.

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $459, price is now $377 per person
$377
per person
Sep 25 - Sep 28
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 helpful staff in our reviews. Popular attractions Lake Compounce and Barnes Museum are located nearby.

Hilton Garden Inn Hartford South/Glastonbury

Hilton Garden Inn Hartford South/Glastonbury

3 out of 5
Price was $599, price is now $499 per person
$499
per person
Sep 25 - Sep 28
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 Xfinity Theatre are located nearby.
Excellent had great night sleep. Very comfortable.

Reviewed on Jul 23, 2026

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

3 out of 5
Price was $482, price is now $410 per person
$410
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hill-Stead Museum and Batterson Park Pond are located nearby.
I purchased one room type and didn't know until I arrived that I would not get the type of room I paid for. Besides that it was a good hotel.

Reviewed on Jul 23, 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 $576, price is now $440 per person
$440
per person
Sep 25 - Sep 28
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
Save 100% on your flight
Price was $663, price is now $504 per person
$504
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Inn at Middletown

Inn at Middletown

3.5 out of 5
Washington Street Historic District
Save 100% on your flight
Price was $805, price is now $632 per person
$632
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Landing Apartments West Windsor

Landing Apartments West Windsor

4 out of 5
Price was $645, price is now $511 per person
$511
per person
Sep 25 - Sep 28
found 1 day 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.
Motel 6 Enfield, CT - Hartford

Motel 6 Enfield, CT - Hartford

2 out of 5
Price was $557, price is now $467 per person
$467
per person
Aug 26 - Aug 31
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Delamar West Hartford

Delamar West Hartford

4 out of 5
Save 100% on your flight
Price was $1,543, price is now $1,175 per person
$1,175
per person
Aug 26 - Aug 31
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $1,223, price is now $1,018 per person
$1,018
per person
Aug 26 - Aug 31
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Motel 6 Windsor Locks, CT - Hartford

Motel 6 Windsor Locks, CT - Hartford

2 out of 5
Price was $569, price is now $503 per person
$503
per person
Aug 26 - Aug 31
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)

Top Flight Deals

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

Frontier Airlines
Wed, Sep 2 - Mon, Sep 14
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$156 Roundtrip, found 1 hour ago
$156
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Luis Munoz Marin Intl. to Bradley Intl., returning Mon, Sep 14, priced at $156 found 1 hour ago
Breeze Airways
Thu, Aug 6 - Sat, Aug 22
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$168 Roundtrip, found 4 days ago
$168
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Aug 6 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 22, priced at $168 found 4 days ago
Breeze Airways
Wed, Aug 12 - Mon, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$171 Roundtrip, found 1 hour ago
$171
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Mon, Aug 31, priced at $171 found 1 hour ago
Breeze Airways
Wed, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$186 Roundtrip, just found
$186
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $186 just found