Westport Vacation Packages

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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.

Top Westport Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Apr. 20 - Apr. 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,451 reviews)
Great stay in Portland. Nicest hotel around in my opinion

Reviewed on Feb. 2, 2025

The Weldon Hotel

The Weldon Hotel

4 out of 5
Downtown Portland
per person
Apr. 20 - Apr. 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (35 reviews)
The full kitchen and appliances were perfect for my stay so that I did not have to eat out while I was there and save money

Reviewed on Jan. 20, 2025

River View Resort

River View Resort

2.5 out of 5
per person
Mar. 5 - Mar. 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.8/10 Excellent! (274 reviews)
spacious and convenient for our family of 4 to ski at Sunday River. Our 4th time staying here and always a clean room and friendly staff.

Reviewed on Jan. 1, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
per person
Apr. 20 - Apr. 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (248 reviews)
this property was everything that I hoped it would be. I was looking for a quiet and relaxing place to spend the night before flying home after attending a conference. I stayed in a standard room in the main part of the hotel with a room overlooking the the beach and the water. This is my first time to Maine, and everything has been absolutely wonderful, especially the way the rocks and the water and the beach and the trees glisten in the snow. i’m already planning my trip back to The Inn by the Sea…

Reviewed on Jan. 27, 2025

And. N B&B

And. N B&B

3 out of 5
per person
Apr. 5 - Apr. 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.8/10 Exceptional! (56 reviews)
It's winter, house has central and each room has a split heatpump soooo nice and comfy. Located on not-so-traveled road yet central to village makes it pretty quiet. Definitely Dog Lovers - pet friendly ice-melt/couple waste bags/bowls/mat/doggy bed!!!! Thanks

Reviewed on Jan. 19, 2025

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Westport Hotel Deals

Make Shimmering River Retreat your Maine Coastal getaway!
Make Shimmering River Retreat your Maine Coastal getaway!
Westport Island
9.6/10 Exceptional! (33 reviews)
Summer vacation
"Our group used both the main house and the cottage. Both had been cleaned prior to our arrival and the property was very nice. The pool was completely green and had not been taken care of. Luckily weI have a pool and we were able to"

Reviewed on Sep. 18, 2024

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Make Shimmering River Retreat your Maine Coastal getaway!
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
Westport Island
9.4/10 Exceptional! (29 reviews)
Family Christmas
"Absolutely beautiful views. Very well appointed and comfortable."

Reviewed on Dec. 30, 2024

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Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
Doggett Castle Guest House
Doggett Castle Guest House
Westport
9.6/10 Exceptional! (14 reviews)
Doggett Doggy Days
"Our group, and our pooch Junie B, had a wonderful two weeks! The house was spacious which was appreciated as a few people in our party had to work for part of the trip. Either the sleeping porch or TV rooms make great offices by the way. We loved the peek-a-boo view of the Sheepscot River although ..."

Reviewed on Aug. 18, 2024

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Doggett Castle Guest House
See all 1,449 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Westport vacation package cost?
You’ll find cheap prices from CA $1,064 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?

  1. 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.
  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 vacation package that brings all your bookings together.

Discover the most popular places to visit in Westport

Castle Tucker

You can spend an afternoon exploring the galleries in Castle Tucker in Wiscasset. While you're in the area, stroll along the waterfront.

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