Westport Vacations from $569
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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.
Blind Tiger Portland - Danforth Street.
West End
$646
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (189 reviews)
Perfect location & beautiful stay! Very unique property. Great recommendations & lovely hospitality. We will definitely come back the next time we’re in Portland!
:)
Reviewed on Aug 23, 2026
Portland Regency Hotel & Spa
Downtown Portland
$691
per person
Oct 17 - Oct 19
found 19 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (1,740 reviews)
This property was a throwback today's gone by, but in a very charming way. The staff was wonderful, the armory lounge was terrific, and we liked our room. Because of the age of the hotel, there is no room to expand the bathroom. That being said, the shower was comfortable as were the other facilities. The location was fantastic. We would highly recommend this property.
Reviewed on Aug 24, 2026
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
Boothbay: Lighthouses & Islands Harbor Cruise
$41
per adult
94% of travellers recommend
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
$60
per adult
Schooner Eastwind Sunset Sail to see the Maine Coastline
$60
per adult
100% of travellers recommend
Westport Hotel Deals
Unique oceanfront home with a deck, tons of natural light, & amazing views
Westport ME
Flagship Inn and Suites
200 Townsend Avenue Boothbay Harbor ME
$162 nightly
$176 total
Sep 23 - Sep 24
Total with taxes and fees
8/10 Very Good! (1,039 reviews)
"We stayed just one night as we went to a concert at the Opera House which was less than a mile from this hotel. Great location. Room was clean, nothing fancy but had what we needed. Breakfast was included, continental breakfast-the staff kept it stocked. Good enough. Our second stay here. Would stay ..."
Reviewed on Aug 23, 2026
Travelers Inn
130 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
$109 nightly
$119 total
Aug 25 - Aug 26
Total with taxes and fees
9/10 Wonderful! (1,046 reviews)
"Due to travel delays we knew we would be getting to the motel late. We called ahead to ask for a late check in and the office clerk made it work. The room was very clean and the bed, although only full size, was perfectly comfortable. We had a pleasant one night stay."
Reviewed on Aug 24, 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.
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
How much does a Westport vacation package cost?
You'll find cheap prices from $569 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?
January, October and December are great times to look for cheap Westport vacation packages. Traveling in less busy months means you can typically find lower prices on flights and accommodations.
How many days is enough for Westport?
Typically, a handful of days is enough to explore the major sights during your Westport vacation. But if you prefer to have time to kick back or go on day trips, consider extending your itinerary.
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.
Does Expedia offer Book Now, Pay Later Westport vacation packages?
Your Westport break should be a relaxing escape from your busy life, not a source of money worries. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
