Westport Vacations from $569
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Westport Vacation
With a vacation package to Westport, say goodbye to travel planning and hello to trouble-free adventure. Every detail of your getaway has been taken care of before you go, so you can get on with experiencing this exciting city. If your trip to Westport includes a little sightseeing, check out well-known attractions like Brooks Point, Castle Tucker and Monkey C Monkey Do. Browse Expedia's wide range of travel options and begin planning your ideal vacation to Westport today.
The Latest Westport vacation packages
Price found within the past 48 hours. Click for updated prices.
Nautical Mile
Price was $712, price is now $569 per person
$569
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.6/10 Excellent! (25 reviews)
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.
Reviewed on Sep 8, 2026
84 Main
Price was $1,026, price is now $873 per person
$873
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.8/10 Exceptional! (58 reviews)
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.
Reviewed on Jul 17, 2026
Stay near popular Westport attractions
What to do in Westport
Boothbay Harbor: Boos and Brews Walking Ghost Tour
$33
per adult
Spooks and Spirits Walking Ghost Tour of Boothbay Harbor
$33
per adult
90-Minute Ghost Walking Tour in Boothbay Harbor
$30
per adult
100% of travellers recommend
Westport Hotel Deals
Waterfront Retreat on Westport Island | Sunrooms, Fire pit & Water Views
Wiscasset ME
10/10 Exceptional! (1 review)
"Very comfortable and well outfitted place. More updated than many Maine properties. Well provisioned especially with coffee and coffee related stuff. Nice views, especially from the two water-view sunrooms. Even though the weather was chilly, there were space heaters that made those rooms comfortable ..."
Reviewed on Oct 26, 2026
The Brunswick Hotel
4 Noble St Brunswick ME
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $131 total per night from Nov 9 to Nov 10
$131 total
Nov 9 - Nov 10
Total with taxes and fees
Moonlight Inn
215 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $97 total per night from Nov 1 to Nov 2
$97 total
Nov 1 - Nov 2
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Westport Vacation Packages
Westport Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Augusta State Airport (AUG) |
Population | 780 |
Top Sights | Monkey C Monkey Do, Castle Tucker and Lincoln County Jail Museum |
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
