Westport Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Westport Vacation
With a Westport vacation package, say goodbye to travel planning and hello to an effortless adventure. Every detail of your escape has been taken care of before departing, so you can make the most of your time experiencing this fantastic city. Depot Theatre is just one of the top attractions to check off your itinerary during a trip to Westport. No matter your travel plans or the size of your budget, putting together the ultimate tailored Westport vacation is a walk in the park with Expedia.
Top Westport Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Tälta Lodge, A Bluebird by Lark
CA $1,933
per person
Sep 17 - Sep 23
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9.2/10 Wonderful! (1,009 reviews)
Clean quiet hotel. Good water pressure in the shower. Only issue was you had to lean on the bathroom door to get it to latch and pull hard on the door leading to the deck to get it to open.
Reviewed on Aug 12, 2026
Hilton Garden Inn Burlington Downtown
Downtown Burlington
CA $2,226
per person
Sep 17 - Sep 23
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
8.8/10 Excellent! (1,008 reviews)
property is at a great location. walkable to restaurants and shops. Staff are aways friendly.
Reviewed on Aug 11, 2026
Ready to book your vacation to Westport?
Westport Hotel Deals
The Inn in Westport
1234 Stevenson Rd Westport NY
CA $271
CA $307 total
Aug 13 - Aug 14
includes taxes & fees
9.2/10 Wonderful! (190 reviews)
"Wonderfully helpful staff, beautiful accommodations, extremely comfortable. Bed. Would definitely stay here again. Just lovely."
Reviewed on Aug 8, 2026
DoubleTree by Hilton Burlington Vermont
870 Williston Rd South Burlington VT
Fully refundableReserve now, pay when you stay
CA $205
CA $231 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (2,018 reviews)
"The stay was ruined by the check in,which took well over an hour because of a computer outage. Everything could have been smoothed over by just offering the guests something for their inconvenience like maybe a free breakfast or some refund. But not from this company! The bottom line is always profit. ..."
Reviewed on Aug 12, 2026
Green Mountain Suites Hotel
401 Dorset St South Burlington VT
CA $262
CA $288 total
Aug 30 - Aug 31
includes taxes & fees
9.4/10 Exceptional! (2,017 reviews)
"This property was as good as advertised."
Reviewed on Aug 11, 2026
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.
Stay near popular Westport attractions
Depot Theatre
You can get tickets for a performance at Depot Theatre during your stay in Westport. While you're in the area, stroll along the lakeside.
Westport Town Hall
Westport Town Hall is just one of the places to see in Westport, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the lakeside.
Barber's Point Light
After visiting Barber's Point Light, make a plan to see the other sights and activities in Westport. While you're in the area, stroll along the lakeside.
Ballard Park
After visiting Ballard Park, make a plan to see the other sights and activities in Westport. While you're in the area, stroll along the lakeside.
Westport Marina
Explore the waterfront in Westport with a trip to Westport Marina. While you're in the area, stroll along the lakeside.
Ledge Hill Brewing Company
You can take time to visit Ledge Hill Brewing Company during your travels to Westport. While you're in the area, stroll along the lakeside.
Westport Library Association
After visiting Westport Library Association, make a plan to see the other sights and activities in Westport. While you're in the area, stroll along the lakeside.
The Mill
The Mill is just one of the places to see in Westport, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the lakeside.
Frequently asked questions
How much does a Westport vacation package cost?
You'll find cheap prices from CA $1,833 on Expedia for your Westport escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Westport costs.
What are the cheapest months to go to Westport?
To pick up cheap Westport vacation packages, plan your trip outside of peak periods like public holidays and major festivals. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Westport?
The ideal length for your Westport vacation depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to check out all the main sights and explore some hidden spots along the way.
How to find the best Westport package deals?
Use Expedia's handy filters to help you find some unbeatable Westport package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Westport package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Westport vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still get the flexibility to create a customized Westport vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Westport?
If you're planning an impromptu Westport vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Westport?
- Choose when to get away: Check your calendar and get packing. Your preferred season and the activities on offer will also help you decide when to visit Westport.
- Set a budget: Consider expenses such as flights, food and transportation when calculating how much to save for your trip to Westport. Then, select a hotel that works with your budget, whether that's a low-cost stay or a swankier getaway.
- Decide how long to go away for: Now that you're more familiar with Westport, you can figure out the right length of your break. Put together a rough plan and give yourself enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalized Westport vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
