Westport Holidays

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Top hotels in Westport

Make Shimmering River Retreat your Maine Coastal getaway!

Make Shimmering River Retreat your Maine Coastal getaway!

Westport Island
9.6/10 Exceptional! (35 reviews)
"Check in was easy. The kitchen was extremely well stocked down to a lobster pot to our delight.The setting is beautiful and we very much enjoyed the two level deck. There is a bit of a hike to get to the river. All and all a very peaceful relaxing location. We had 9 adults and 4 children and were ..."

Reviewed on 9 Aug 2025

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Make Shimmering River Retreat your Maine Coastal getaway!
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! (94 reviews)
"A beautiful home in a beautiful place. Perfect for large families."

Reviewed on 17 Aug 2025

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Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
WATERFRONT Retreat venue for up to 60 guests!… Weddings, Reunions, Meetings!……

WATERFRONT Retreat venue for up to 60 guests!… Weddings, Reunions, Meetings!……

Westport Island
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WATERFRONT Retreat venue for up to 60 guests!… Weddings, Reunions, Meetings!……
See all 1,655 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.

Popular places to visit

Monkey C Monkey Do

Enjoy a trip to Monkey C Monkey Do and popular activities such as boating in Wiscasset. While you're in the area, stroll along the waterfront.

Monkey C Monkey Do

What to do in Westport

Boothbay Harbor Cruise: Lighthouses, Lobster Haul, and Seals

Boothbay Harbor Cruise: Lighthouses, Lobster Haul, and Seals

€35
per adult
100% of travellers recommend
Boothbay Harbor Cruise: Lighthouses, Lobster Haul, and Seals
Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

€52
per adult
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
Boothbay Harbor Culinary Walking Tour

Boothbay Harbor Culinary Walking Tour

€138
per adult
Boothbay Harbor Culinary Walking Tour
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.