Westport Vacations from $241

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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.

The Latest Westport vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Portland Airport

Hilton Garden Inn Portland Airport

3 out of 5
Save 100% on your flight
Price was $337, price is now $241 per person
$241
per person
Jan 29 - Feb 2
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.4/10 Very Good! (1,001 reviews)
Nice , clean friendly place

Reviewed on Dec 15, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $442, price is now $284 per person
$284
per person
Jan 29 - Feb 2
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Lovely stay in a beautiful room, appreciated the upgrade. Easy walk to downtown activities.

Reviewed on Dec 12, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,146, price is now $772 per person
$772
per person
Jan 29 - Feb 2
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
My husband and I had a wonderful time. Breakfast, lunch, and dinner was delicious, drinks were crafted just right. We absolutely loved the outdoor hot tub. Our stay was everything we expected. Thank you.

Reviewed on Dec 8, 2025

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
Save 100% on your flight
Price was $355, price is now $252 per person
$252
per person
Jan 29 - Feb 2
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (1,121 reviews)
Parking is not available to the airport if you book through Expedia. They only honor parking with direct bookings. We were able to find parking at the airport and the hotel does offer a 24 hour shuttle. The front desk was not able to change our reservation and was bluntly unhelpful. I know the staff doesn't set policy and they probably deal with this issue all the time. Parking should be taken of Expedia as an offering.

Reviewed on Dec 15, 2025

River View Resort

River View Resort

2.5 out of 5
Save 100% on your flight
Price was $663, price is now $472 per person
$472
per person
Mar 1 - Mar 5
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
8.8/10 Excellent! (297 reviews)
It was a basic suite-like motel. Could use an upgrade. Very 70s

Reviewed on Mar 30, 2025

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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.

Castle Tucker

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.

Lincoln County Jail Museum

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.

Monkey C Monkey Do

Westport Hotel Deals

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

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

Westport Island ME
Get rates
WATERFRONT Retreat venue for up to 60 guests!… Weddings, Reunions, Meetings!……
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

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

Westport ME
8/10 Very Good! (30 reviews)
Spectacular Location
We loved the location of this property. The wrap around porch overlooking the water was amazing. The kitchen was equipped for what we needed and there was plenty of space to relax. The property itself needs some TLC. Many of the windows are inoperable and those that worked had screens that were in ...

Reviewed on Aug 7, 2025

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Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
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 ME
9.8/10 Exceptional! (97 reviews)
Beautiful House, a perfect getaway

Reviewed on Dec 8, 2025

Get rates
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
See all 1,608 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 $241 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.