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Westbrook 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.

Kennebunkport Captains Collection
Price was $1,485, price is now $1,201 per person
$1,201
per person
Dec 31 - Jan 5
just found
Roundtrip flight included
Dallas (DFW) 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.

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 1 day 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.

The Docent's Collection at 121 Middle Street
Price was $1,597, price is now $1,379 per person
$1,379
per person
Dec 17 - Dec 23
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions State Theatre and Thompson's Point are located nearby.
The property was excellent. We stayed in a 1 bedroom loft and it was great. Nice sitting area, fully equipped kitchen, beautiful bathroom and nice size bedroom. It was quiet and comfy, and also walking distance to great restaurants. Highly recommend.
Reviewed on Nov 12, 2026

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.
Beautiful place, great location
Reviewed on Nov 12, 2026
Westbrook Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Westbrook 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 17 hours ago
$219
Roundtrip
found 17 hours ago

Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$249 Roundtrip, found 13 hours ago
$249
Roundtrip
found 13 hours ago

Sun, Feb 28 - Wed, Mar 10
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$267 Roundtrip, found 6 hours ago
$267
Roundtrip
found 6 hours ago

Sat, Dec 5 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
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