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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.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $392, price is now $352 per person
$352
per person
Dec 3 - Dec 6
found 1 hour ago
Roundtrip flight included
Nashville (BNA) 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 Panthorn Park and Cheshire Hollow Farm are located nearby.
We enjoyed our stay at the holiday in. We went for a Texas Tenor concert on 17 sep. We spent 2 nights there. Hotel was nice and clean. The beds were comfortable. The only issue we had was the maid had left the window open and we didnt see it for a while. A few mosquitos got in. Suggest they use screens if they are going to open windows. We didnt eat there or use the pool. The pool looked wonderful tho. Employees at the desk were very nice and helpful. We would stay again.

Reviewed on Sep 20, 2026

Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $1,169, price is now $871 per person
$871
per person
Nov 25 - Nov 30
found 12 hours 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 Sperry Park 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.

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

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $669, price is now $549 per person
$549
per person
Nov 13 - Nov 15
found 3 hours ago
Roundtrip flight included
San Juan (SJU) 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.

Simsbury Inn

Simsbury Inn

3.5 out of 5
Price was $1,311, price is now $1,136 per person
$1,136
per person
Nov 25 - Nov 30
found 12 hours ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this business-friendly hotel in Weatogue. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosedale Farms & Vineyards and Stratton Brook State Park are located nearby.
Very nice hotel for a few days stay near where I grew up. The walking trail and flower bridge were great finds.

Reviewed on Sep 17, 2026

The Goodwin Hotel

The Goodwin Hotel

3.5 out of 5
Price was $1,190, price is now $1,049 per person
$1,049
per person
Nov 25 - Nov 30
found 12 hours ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Stay at this hotel in Hartford. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PeoplesBank Arena and The Meadows Music Theatre are located nearby.
Always a nice place to stay close to Trinity College to watch football games.

Reviewed on Sep 21, 2026

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

2.5 out of 5
Price was $668, price is now $598 per person
$598
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Book a stay at this family-friendly hotel in Windsor Locks. Enjoy free WiFi, free parking, and a free airport shuttle. 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.

Portland 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 $615, price is now $514 per person
$514
per person
Nov 25 - Nov 29
found 1 hour 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 $1,032, price is now $788 per person
$788
per person
Nov 25 - Nov 29
found 1 hour 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)
Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $1,031, price is now $880 per person
$880
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)

Portland Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $1,169, price is now $871 per person
$871
per person
Nov 25 - Nov 30
found 12 hours ago
Roundtrip flight included
San Juan (SJU) 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)
Simsbury Inn

Simsbury Inn

3.5 out of 5
Simsbury Center
Price was $1,311, price is now $1,136 per person
$1,136
per person
Nov 25 - Nov 30
found 12 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 $1,295, price is now $1,127 per person
$1,127
per person
Nov 25 - Nov 30
found 12 hours ago
Roundtrip flight included
San Juan (SJU) 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.
$155 Roundtrip, found 7 hours ago
$155
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 $155 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.
$183 Roundtrip, found 9 hours ago
$183
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 $183 found 9 hours ago
Breeze Airways
Thu, Oct 22 - Sun, Nov 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$199 Roundtrip, found 11 hours ago
$199
Roundtrip
found 11 hours 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 11 hours ago