Search Deals onFreeport Vacation Packages
Freeport Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Inn at St John Portland In-Town
Price was $784, price is now $674 per person
$674
per person
Jan 25 - Feb 1
found 1 day 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.
The hotel was in downtown Portland near the hospital, which is what I was looking for. I was alone, while my husband was in the hospital. The website for the hotel says "Onsite parking". I set my GPS for the Inn, on a dark rainy night, and it took me to a dark alley. I drove around and around looking for the hotel. No spaces out front. So I pulled over in a panic and called them. The two young people at the desk told me the Onsite Parking lot behind the hotel was Full. I would have to go about a block and a half away to park. All those sidestreets were dark and had no visible signage about parking for the Inn. I was upset. I didn't want to walk thru the dark night in the rain with my luggage. Admittedly, one of them offered to move his car and let me park behind the hotel, but I ultimately got explicit directions from him about where this mystery lot was, and I did park there, after parking illegally out front so I could unload first. The lot on Gilman St was a black hole, with no lights or signage. I felt really scared.
But the hotel is old fashioned and cozy, with narrow hallways and stairs, and my particular single room had a bathroom (all my own) down the hall, which I kept having to lock and unlock. The room wasn't especially charming, but it was clean and had everything I needed, even charger ports. I slept well. The bathroom wasn't a problem, and the room provided a good robe for crossing the hall. Breakfast wasn't much, I grabbed a banana and left.
Reviewed on Nov 12, 2026

Blind Tiger Portland – Carleton Street
Price was $1,562, price is now $1,205 per person
$1,205
per person
Jan 25 - Feb 1
found 1 day 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
Price was $1,134, price is now $933 per person
$933
per person
Jan 25 - Feb 1
found 1 day 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
Price was $1,055, price is now $872 per person
$872
per person
Dec 18 - Dec 21
found 12 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
Price was $1,086, price is now $907 per person
$907
per person
Dec 18 - Dec 21
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.
Price was $2,086, price is now $1,756 per person
$1,756
per person
Dec 28 - Jan 1
found 1 day 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
Price was $938, price is now $813 per person
$813
per person
Jan 25 - Feb 1
found 1 day 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
Price was $798, price is now $695 per person
$695
per person
Jan 15 - Jan 18
found 1 day 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.



Freeport Vacation Packages 5-7 Night Stays
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Feb 15 - Sat, Feb 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 4 hours ago
$219
Roundtrip
found 4 hours ago

Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$249 Roundtrip, just found
$249
Roundtrip
just found

Sun, Feb 28 - Wed, Mar 10
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$267 Roundtrip, found 1 hour ago
$267
Roundtrip
found 1 hour ago

Sat, Dec 5 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 23 hours ago
$277
Roundtrip
found 23 hours ago
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