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.
River View Resort

River View Resort

2.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.8/10 Excellent! (287 reviews)
Great location for skiing at Sunday River

Reviewed on Mar. 2, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,000 reviews)
Beautiful resort! Everything was perfect

Reviewed on Feb. 22, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
May 16 - May 19
found 7 hours ago
Roundtrip non-stop flight included
Cancun (CUN) to Portland (PWM)
9.2/10 Wonderful! (1,467 reviews)
Staff were extremely friendly & helpful. Did not like the extra "destination charge" seems a bit pricy for water, apples & coffee?

Reviewed on Mar. 3, 2025

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
per person
May 16 - May 19
found 7 hours ago
Roundtrip non-stop flight included
Cancun (CUN) to Portland (PWM)
9.8/10 Exceptional! (109 reviews)
Charming place to stay.

Reviewed on Dec. 13, 2024

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
per person
May 16 - May 19
found 7 hours ago
Roundtrip non-stop flight included
Cancun (CUN) to Portland (PWM)
9.6/10 Exceptional! (141 reviews)
Love The Blind Tiger. Fantastic accommodations, lovely staff. Can't wait to go back!

Reviewed on Feb. 10, 2025

Ready to book your vacation to Westport?

 

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Westport Hotel Deals

DISCOUNT WINTER RATES!! Private Coastal Log Cabin with view of the Maine Coast.
DISCOUNT WINTER RATES!! Private Coastal Log Cabin with view of the Maine Coast.
Westport
9.8/10 Exceptional! (80 reviews)
Perfect Winter Getaway
"We had a fantastic winter long weekend at the house with our teenage son. This was our second time staying here. The kitchen was perfectly stocked for cooking our meals and the beds were very comfortable. We relaxed in front of the fireplace and stargazed in the hot tub. The nearby towns are full ..."

Reviewed on Feb. 24, 2025

Get rates
DISCOUNT WINTER RATES!! Private Coastal Log Cabin with view of the Maine Coast.
Fairfield Inn & Suites by Marriott Brunswick Freeport
Fairfield Inn & Suites by Marriott Brunswick Freeport
2.5 out of 5
36 Old Portland Rd, Brunswick, ME
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Mar. 23 to Mar. 24
CA $139
CA $152 total
includes taxes & fees
Mar 23 - Mar 24
8.6/10 Excellent! (356 reviews)
"Very clean and quiet"

Reviewed on Feb. 16, 2025

Fairfield Inn & Suites by Marriott Brunswick Freeport
Hilton Garden Inn Freeport Downtown
Hilton Garden Inn Freeport Downtown
3 out of 5
5 Park St, Freeport, ME
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Mar. 23 to Mar. 24
CA $145
CA $158 total
includes taxes & fees
Mar 23 - Mar 24
9/10 Wonderful! (1,004 reviews)
"It was a great stay with friendly people"

Reviewed on Mar. 2, 2025

Hilton Garden Inn Freeport Downtown
See all 1,520 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 $875 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.