Westport Vacations from ￥327,648
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The Latest Westport Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Blind Tiger Portland - Danforth Street.
West End
￥416,999
per person
Dec 7 - Dec 11
found 12 hours ago
Roundtrip flight included
Nagoya (NGO) to Portland (PWM)
9.6/10 Exceptional! (193 reviews)
Staying at the Blind Tiger truly enhanced our experience in Portland. The hotel is thoughtfully planned with tasteful common areas. The rooms were chic and I loved the fireplace in our room.
Reviewed on Oct 3, 2026
Evalina Hotel
Downtown Portland
￥352,296
per person
Dec 7 - Dec 11
found 12 hours ago
Roundtrip flight included
Nagoya (NGO) to Portland (PWM)
10/10 Exceptional! (13 reviews)
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.
Reviewed on Oct 5, 2026
Find the Best Westport Vacation Packages
Westport Hotel Deals
Make Shimmering River Retreat your Maine Coastal getaway!
Westport Island ME
9.8/10 Exceptional! (49 reviews)
"What a beautiful property and houses. The host is unbelievable in so many ways. The communication and responsiveness is second to none. The pictures in the listing are very accurate and the kitchen is very well stocked with everything that you need and then some! We had seven people in our party ..."
Reviewed on Sep 15, 2026
The Brunswick Hotel
4 Noble St Brunswick ME
￥15,836
￥17,261 total
Nov 4 - Nov 5
includes taxes & fees
Moonlight Inn
215 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
￥13,283
￥14,478 total
Nov 1 - Nov 2
includes taxes & fees
7.6/10 Good! (783 reviews)
"Low mirrors ,small vanity, no shelves in bathroom"
Reviewed on Oct 5, 2026
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.
Stay near popular Westport attractions
Brooks Point
10.0/10 (2 reviews)
Commune with nature and explore the great outdoors at Brooks Point during your travels in Westport.
What to do in Westport
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
￥9,405
per adult
Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise
￥8,621
per adult
Boos and Brews Walking Ghost Tour of Boothbay Harbor
￥5,177
per adult
100% of travellers recommend
Frequently asked questions
How much does a Westport vacation package cost?
You'll find cheap prices from ￥327,648 on Expedia for your Westport getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Westport costs.
What are the cheapest months to go to Westport?
The off-season is the best time to head to Westport if you're trying to save. Another tip for scoring cheap Westport vacation packages? Avoid visiting during public holidays and any major events or festivals.
How many days is enough for Westport?
With a well-planned schedule, you can easily visit the most popular Westport attractions in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Westport vacation for longer.
How to find the best Westport package deals?
Use Expedia's filter tool to help you find some great Westport package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Westport package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Westport vacation as a package?
You can enjoy significant savings on your next Westport break by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Westport?
Secure amazing discounts by reserving your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Westport vacation.
How to plan a trip to Westport?
- Choose when to get away: Check your calendar and get packing. Your favorite time of year and the type of activities on offer will also help you decide when to visit Westport.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will probably be the biggest expense during your trip to Westport.
- Work out your trip length: Think about how much time you want to spend discovering Westport. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Westport vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.