Search Deals on
Portland Vacation Packages

Build your package with 2 more options

Portland Flight + Hotel Packages

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 $637, price is now $528 per person
$528
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.
Staff friendly

Reviewed on Sep 20, 2026

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 18 hours 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

Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was $934, price is now $747 per person
$747
per person
Nov 23 - Nov 27
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 Sperry Park are located nearby.

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 18 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.

The Cromwell Inn

The Cromwell Inn

2.5 out of 5
Price was $634, price is now $546 per person
$546
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.

Residence Inn by Marriott Hartford Downtown

Residence Inn by Marriott Hartford Downtown

3.5 out of 5
Price was $836, price is now $722 per person
$722
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this business-friendly hotel in Hartford. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular attractions PeoplesBank Arena and The Meadows Music Theatre are located nearby.

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $668, price is now $578 per person
$578
per person
Nov 23 - Nov 27
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 Crystal Bees and Hawks Landing Country Club 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 $637, price is now $528 per person
$528
per person
Nov 23 - Nov 27
found 1 day 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 18 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 $934, price is now $747 per person
$747
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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 18 hours 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.
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

2.5 out of 5
Price was $788, price is now $636 per person
$636
per person
Nov 7 - Nov 14
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
Price was $1,169, price is now $871 per person
$871
per person
Nov 25 - Nov 30
found 1 hour 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)
Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $822, price is now $660 per person
$660
per person
Nov 7 - Nov 14
found 1 day 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 - Thu, Nov 19
MCO
Orlando Intl.
BDL
Bradley Intl.
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Orlando Intl. to Bradley Intl., returning Thu, Nov 19, priced at $155 found 1 day ago
American Airlines
Wed, Oct 21 - Wed, Oct 28
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$180 Roundtrip, found 1 day ago
$180
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 $180 found 1 day ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$183 Roundtrip, found 2 hours ago
$183
Roundtrip
found 2 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 2 hours ago
Breeze Airways
Thu, Oct 22 - Sun, Nov 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour 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 hour ago