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Portland Vacation Packages

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Portland 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 $616, price is now $508 per person
$508
per person
Dec 1 - Dec 4
found 10 hours 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.

Simsbury 1820 House

Simsbury 1820 House

4 out of 5
Price was $1,100, price is now $853 per person
$853
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Book a stay at this business-friendly B&B in Simsbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Performing Arts Center at Simsbury Meadows and Rosedale Farms & Vineyards are located nearby.

Inn on Storrs

Inn on Storrs

3.5 out of 5
Price was $906, price is now $716 per person
$716
per person
Nov 24 - Dec 1
found 6 hours 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.

Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $1,126, price is now $892 per person
$892
per person
Nov 25 - Nov 29
just found
Roundtrip flight included
Atlanta (ATL) 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.

Landing Apartments Vernon

Landing Apartments Vernon

3.5 out of 5
Price was $1,149, price is now $910 per person
$910
per person
Oct 27 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $691, price is now $587 per person
$587
per person
Nov 25 - Nov 29
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Breakfast was good, pool was saltwater and heated, breakfast was small but good. The only neutral thing was no coffee makers in the room but they have a 24/7 one in the lobby.

Reviewed on Sep 21, 2026

Inn at Middletown

Inn at Middletown

3.5 out of 5
Price was $635, price is now $546 per person
$546
per person
Oct 23 - Oct 25
found 19 hours ago
Roundtrip non-stop 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.
We found our room was not carefully cleaned when we checked in. It was not good to find a bridge threader on the floor. We did not appreciate the amenities fee that was tacked on after we booked. The location was good and the hot water in the lobby was handy. The beds were comfy. We will look elsewhere next time we are in the area.

Reviewed on Sep 21, 2026

The Cromwell Inn

The Cromwell Inn

2.5 out of 5
Price was $651, price is now $564 per person
$564
per person
Nov 25 - Nov 29
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) 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.

Portland 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 $616, price is now $508 per person
$508
per person
Dec 1 - Dec 4
found 10 hours ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Simsbury 1820 House

Simsbury 1820 House

4 out of 5
Simsbury Center
Price was $1,100, price is now $853 per person
$853
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $1,126, price is now $892 per person
$892
per person
Nov 25 - Nov 29
just found
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $691, price is now $587 per person
$587
per person
Nov 25 - Nov 29
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)

Portland Vacation Packages 5-7 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 $647, price is now $492 per person
$492
per person
Nov 25 - Nov 30
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 $1,103, price is now $807 per person
$807
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Inn on Storrs

Inn on Storrs

3.5 out of 5
Price was $906, price is now $716 per person
$716
per person
Nov 24 - Dec 1
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
Landing Apartments Vernon

Landing Apartments Vernon

3.5 out of 5
Price was $1,149, price is now $910 per person
$910
per person
Oct 27 - Nov 2
found 1 day 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
Thu, Nov 12 - Mon, Nov 16
MCO
Orlando Intl.
BDL
Bradley Intl.
$146 Roundtrip, found 7 hours ago
$146
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Orlando Intl. to Bradley Intl., returning Mon, Nov 16, priced at $146 found 7 hours ago
American Airlines
Wed, Oct 21 - Wed, Oct 28
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$180 Roundtrip, found 2 days ago
$180
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Oct 21 from Ronald Reagan Washington National to Bradley Intl., returning Wed, Oct 28, priced at $180 found 2 days ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$185 Roundtrip, found 9 hours ago
$185
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $185 found 9 hours ago
Breeze Airways
Thu, Oct 22 - Sun, Nov 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Oct 22 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Nov 8, priced at $199 found 1 day ago