Westport Vacation Packages 2026 from $760

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.

Portland Harbor Hotel

Downtown Portland

Save 100% on your flight

$760

per person

May 11 - May 16

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.2/10 Wonderful! (1,776 reviews)

Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.

Reviewed on Mar 24, 2026

The Docent's Collection at 121 Middle Street

Downtown Portland

Save 100% on your flight

$803

per person

May 11 - May 16

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.6/10 Exceptional! (275 reviews)

Property is in an excellent location with so much to see and do (and eat) in walking distance. My room was clean, quiet, and well maintained. Staff interaction was minimal (by design) but the few times I spoke with the concierge on site she was pleasant and accommodating. My only negative comment is regarding the toiletry products. I’m a toilet paper snob and that angel soft just doesn’t cut it. Overall I am beyond satisfied with my stay and would absolutely stay here again.

Reviewed on Mar 22, 2026

Ogunquit River Inn & Suites

$803

per person

May 5 - May 11

found 10 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Portland (PWM)

9/10 Wonderful! (1,000 reviews)

The room was very clean!

Reviewed on Oct 31, 2025

Inn By The Sea

Save 100% on your flight

$1,249

per person

Jun 16 - Jun 20

found 4 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.4/10 Exceptional! (304 reviews)

Such a beautiful place, great to walk on beach, nice view, staff great.. cozy place.. so well decorated.. highly recommend for a nice quiet get away

Reviewed on Mar 4, 2026

Cliff House Maine

Bald Head

Save 100% on your flight

$1,491

per person

Jun 4 - Jun 7

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Portland (PWM)

9.4/10 Exceptional! (1,007 reviews)

Check in was smooth and set the tone for a relaxed upscale experience. Valet available and doorman took our bags to the room. Room was great, beautiful ocean view, soft and silky sheets/down bedding. Pool and hot tub were amazing. Was so beautiful and peaceful hearing the waves crash against the rocks. Well worth it!

Reviewed on Mar 24, 2026

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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.

Monkey C Monkey Do

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

Lincoln County Jail Museum

You can spend an afternoon browsing the exhibits at Lincoln County Jail Museum during your travels in Wiscasset. While you're in the area, stroll along the waterfront.

Westport Hotel Deals

Make Shimmering River Retreat your Maine Coastal getaway!

Westport Island ME

9.6/10 Exceptional! (40 reviews)

Amazing home in an amazing setting. Extremely responsive host.

Reviewed on Sep 29, 2025

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Residence Inn Bath Brunswick Area

139 Richardson St. Bath ME

Fully refundableReserve now, pay when you stay

$144 nightly

$157 total

Mar 30 - Mar 31

Total with taxes and fees

9.6/10 Exceptional! (389 reviews)

everything was great

Reviewed on Mar 10, 2026

The Brunswick Hotel

4 Noble St Brunswick ME

Fully refundableReserve now, pay when you stay

$122 nightly

$134 total

Apr 7 - Apr 8

Total with taxes and fees

9.4/10 Exceptional! (918 reviews)

Clean room, friendly staff, in walking distance to everything great view

Reviewed on Mar 20, 2026

See all 1,617 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.

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

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Frequently asked questions

How much does a Westport vacation package cost?

You'll find cheap prices from $760 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.

Westport Vacations from $760

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Your Westport Vacation

The Latest Westport vacation packages

Portland Harbor Hotel

The Docent's Collection at 121 Middle Street

Ogunquit River Inn & Suites

Inn By The Sea

Cliff House Maine

Discover the most popular places to visit in Westport

Castle Tucker

Monkey C Monkey Do

Lincoln County Jail Museum

Westport Hotel Deals

Make Shimmering River Retreat your Maine Coastal getaway!

Residence Inn Bath Brunswick Area

The Brunswick Hotel

Find the Best Westport Vacation Packages

Westport Essential Information

More vacations you might like

Frequently asked questions

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