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Freeport Vacation Packages

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Freeport Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
Price was $784, price is now $674 per person
$674
per person
Jan 25 - Feb 1
found 24 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Price was $1,562, price is now $1,205 per person
$1,205
per person
Jan 25 - Feb 1
found 24 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions State Theatre and Cross Insurance Arena are located nearby.
Quick responses by staff! Comfortable bed! Gorgeous amenities! Loved the location was right down from Tandem Coffee!

Reviewed on Oct 21, 2026

The Kendall Inn

The Kendall Inn

3.5 out of 5
Price was $1,134, price is now $933 per person
$933
per person
Jan 25 - Feb 1
found 24 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Portland (PWM)
Stay at this B&B in Freeport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,055, price is now $872 per person
$872
per person
Dec 18 - Dec 21
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Marginal Way and Ogunquit Beach are located nearby.
Room was clean, bathroom too small and risky slippery tub, desk staff with not customers service skills, website said breakfast Included BUT just warm coffee with some croissants don't have to be considered "Breakfast", need to look other places around to get real Breakfast. Other amenities like pool and hot tub was good.

Reviewed on Nov 11, 2026

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,114, price is now $926 per person
$926
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Kennebunkport Village Green are located nearby.

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $2,086, price is now $1,756 per person
$1,756
per person
Dec 28 - Jan 1
found 20 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions State Theatre and Cross Insurance Arena are located nearby.

Dormir

Dormir

3 out of 5
Price was $938, price is now $813 per person
$813
per person
Jan 25 - Feb 1
found 24 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Portland (PWM)
Book a stay at this business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Seacoast Adventure and Sebago Lake Basin are located nearby.

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $798, price is now $695 per person
$695
per person
Jan 15 - Jan 18
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
We had a great stay!

Reviewed on Nov 11, 2026

Freeport Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,055, price is now $872 per person
$872
per person
Dec 18 - Dec 21
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,114, price is now $926 per person
$926
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,160, price is now $969 per person
$969
per person
Dec 28 - Jan 1
found 20 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $2,086, price is now $1,756 per person
$1,756
per person
Dec 28 - Jan 1
found 20 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)

Freeport Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Kendall Inn

The Kendall Inn

3.5 out of 5
Price was $1,134, price is now $933 per person
$933
per person
Jan 25 - Feb 1
found 24 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Portland (PWM)
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,562, price is now $1,205 per person
$1,205
per person
Jan 25 - Feb 1
found 24 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,404, price is now $1,152 per person
$1,152
per person
Dec 26 - Jan 1
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,291, price is now $1,083 per person
$1,083
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

Top Flight Deals

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

American Airlines
Mon, Feb 15 - Sat, Feb 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, just found
$219
Roundtrip
just found
Select American Airlines flight, departing Mon, Feb 15 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Feb 20, priced at $219 just found
Breeze Airways
Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$239 Roundtrip, found 17 hours ago
$239
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Wed, Feb 24 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Feb 27, priced at $239 found 17 hours ago
American Airlines
Sat, Dec 5 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 19 hours ago
$277
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sat, Dec 5 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Dec 8, priced at $277 found 19 hours ago
United
Tue, Dec 8 - Mon, Dec 14
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$282 Roundtrip, found 8 hours ago
$282
Roundtrip
found 8 hours ago
Select United flight, departing Tue, Dec 8 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Mon, Dec 14, priced at $282 found 8 hours ago