Westbrook Vacations from $487

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Your Westbrook Vacation

Renowned for its coastal scenery and laid-back lifestyle, Westbrook is the perfect getaway destination. Book one of our Westbrook vacation packages and experience all that this exciting city has to offer. Make your trip to Westbrook even more enjoyable by including some sightseeing. Hammonasset Beach State Park, Essex Steam Train and Clinton Crossing Premium Outlets are among the most popular attractions worth exploring. Check out Expedia's extensive range of travel options and book your ideal vacation to Westbrook today.

The Latest Westbrook vacation packages

Price found within the past 48 hours. Click for updated prices.
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Westbrook Hotel Deals

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
$254 nightly
The price is $292 total per night from Sep 7 to Sep 8
$292 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Clean, comfortable stay. Beautiful resort! Would stay again!"

Reviewed on Aug 19, 2025

Water's Edge Resort & Spa
The Captain Stannard

The Captain Stannard

3 out of 5
138 South Main Street, Westbrook, CT
$238 nightly
The price is $264 total per night from Sep 21 to Sep 22
$264 total
Sep 21 - Sep 22
Total with taxes and fees
9.6/10 Exceptional! (237 reviews)
"It’s a very classy joint. The people there were very nice to us. The community room is huge and filled with beverages, including hot tea. And the conversations we had with the people were wonderful."

Reviewed on Aug 22, 2025

The Captain Stannard
Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
976 Boston Post Rd, Westbrook, CT
$222 nightly
The price is $246 total per night from Sep 23 to Sep 24
$246 total
Sep 23 - Sep 24
Total with taxes and fees
9.8/10 Exceptional! (159 reviews)
"Nice inn setup. Convenient location to beach, and shopping, sightseeing."

Reviewed on Aug 23, 2025

Westbrook Inn B&B
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.

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Frequently asked questions

How much does a Westbrook vacation package cost?
Offering great value package deals from $487 on Expedia, you'll be surprised at how little a vacation to Westbrook costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Westbrook?
If you'd like to snag a cheap Westbrook vacation package, consider traveling in July, September and December. You're likely to find lower prices on hotels and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for Westbrook?
With a well-organized schedule, you can easily visit the most popular Westbrook sights in a few days. But if you'd like to discover hidden gems or go on day trips, think about booking your Westbrook vacation for longer.
Is it worth booking a vacation package to Westbrook?
From cool attractions such as Westbrook Town Beach and Tanger Outlets to its epic views, a Westbrook vacation delivers big on experiences. With so much to see and do, it's time to find out for yourself why Westbrook is such a good vacation destination.
How to find the best Westbrook package deals?
Landing a cheap Westbrook package deal is a cinch with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply some filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Westbrook package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Westbrook vacation as a package?
You can enjoy significant savings on your Westbrook break by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Westbrook?
If you're planning a spontaneous Westbrook trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Westbrook vacation packages?
Your Westbrook break is meant to be an escape from your busy life, not a source of money worries. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs 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.