Westport Holidays

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Your Westport Holiday

When an adventure in the city is calling, answer it with a holiday package to Westport. With all your travel plans in place before you leave, all you have to do here is concentrate on having a blast. You'll want to go sightseeing during your trip to Westport. Drop by top attractions such as Monkey C Monkey Do, Castle Tucker and Brooks Point. That dream Westport holiday is a couple of clicks away. Search flights, accommodation and more on Expedia for a trip that's tailored to suit your travel style.

Westport Holiday

Our pick of the best Westport Hotel Deals

Unique oceanfront home with a deck, tons of natural light, & amazing views

Unique oceanfront home with a deck, tons of natural light, & amazing views

Wiscasset
8.4/10 Very Good! (37 reviews)
Great House
"We loved this property and had a great time staying here. It was clean and check in/check out were a breeze. Nothing better than a cup of coffee on the porch watching the wildlife on the water in the morning!"

Reviewed on 5 Jun. 2025

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Unique oceanfront home with a deck, tons of natural light, & amazing views
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.

Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.

Westport
9.8/10 Exceptional! (88 reviews)
Great place to relax
"This was our 2nd stay at this VRBO house. Needless to say we liked it enough the first time we went back. Very quiet, spacious with neat grounds. I'd very much recommend to others."

Reviewed on 11 Jul. 2025

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Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Westport
8/10 Very Good! (27 reviews)
3 night stay friends get away
"We checked in no problem. We discovered shortly after 4 pm we had no water. I got in touch with Vacasa to inform them that we had no water. They said they would contact the local team and they would be in touch with us. This went on all through the evening with the same response except they always ..."

Reviewed on 21 May 2025

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Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
See all 1,630 properties in Westport
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.

What to do in Westport

Boothbay: Lighthouses & Islands Harbor Cruise

Boothbay: Lighthouses & Islands Harbor Cruise

AU$62
per adult
94% of travellers recommend
Boothbay: Lighthouses & Islands Harbor Cruise
Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

AU$84
per adult
Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise
Boothbay Harbor: Schooner Apple Jack Sunset Sailing Cruise

Boothbay Harbor: Schooner Apple Jack Sunset Sailing Cruise

AU$91
per adult
100% of travellers recommend
Boothbay Harbor: Schooner Apple Jack Sunset Sailing Cruise
See all activities in Westport

Frequently asked questions

How much does a Westport holiday package cost?
You'll find cheap prices on Expedia for your Westport getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your holiday 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 holiday 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 holiday 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 holiday package well in advance.
Is it cheaper to book a Westport holiday as a package?
You can enjoy significant savings on your next Westport break by booking a customised holiday package. Check the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday 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 holiday.
How to plan a trip to Westport?

  1. Choose when to get away: Check your calendar and get packing. Your favourite time of year and the type of activities on offer will also help you decide when to visit Westport.
  2. 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.
  3. 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.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Westport holiday package that brings all your bookings together.