Westbrook Vacations from $500

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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.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $658, price is now $500 per person
$500
per person
Dec 31 - Jan 6
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.2/10 Very Good! (1,002 reviews)
From day one had a good experience. Everything was explained to me in detail and felt very comfortable. From the room and all. Super clean and comfortable. Personally I have no complaints at all. Thank you

Reviewed on Nov 23, 2025

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $767, price is now $531 per person
$531
per person
Dec 31 - Jan 6
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9/10 Wonderful! (1,874 reviews)
Spotless and spacious room. Exceptional front desk staff. Great location a short walk from Yale University. Welcoming lobby with mini-shop for snacks, drinks, necessities. Beer, wine, other beverages in lobby. We loved our stay here!

Reviewed on Nov 26, 2025

Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

2.5 out of 5
Price was $797, price is now $608 per person
$608
per person
Dec 31 - Jan 6
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.4/10 Very Good! (1,000 reviews)
Clean room, friendly and helpful staff. Easy access to I95 North and South. Multiple restaurants nearby.

Reviewed on Nov 24, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $840, price is now $647 per person
$647
per person
Dec 31 - Jan 6
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Nice throwback hotel. Room was spotless, much old school charm. Check in was a little bumpy, otherwise a good stay.

Reviewed on Nov 17, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $680, price is now $532 per person
$532
per person
Dec 31 - Jan 6
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
They didn't give us the room type we booked on Expedia for our first night. After much back and forth, they made us shift into the right room type on our second day at the property. Guests had to sleep on sofa beds for the first night, hotel blamed this on Expedia not communicating properly with the hotel about our reservation. Besides this hassle, our stay was great and would recommend the hotel to everyone. Overpriced parking but great vibes, well furnished etc.

Reviewed on Nov 25, 2025

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Discover the most popular places to visit in Westbrook

Westbrook Town Beach

5/5(1 review)

Why not spend a lazy afternoon at Westbrook Town Beach during your trip to Westbrook?

Westbrook Town Beach

Tanger Outlets

4.5/5(181 reviews)

You can find the perfect gifts to bring home at Tanger Outlets during your trip to Westbrook. While you're in the area, stroll along the beautiful beaches.

Tanger Outlets

Westbrook Hotel Deals

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
$175 nightly
The price is $202 total per night from Nov 30 to Dec 1
$202 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,007 reviews)
Staff is fantastic

Reviewed on Nov 24, 2025

Water's Edge Resort & Spa
The Captain Stannard

The Captain Stannard

3 out of 5
138 South Main Street Westbrook CT
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $176 total per night from Dec 4 to Dec 5
$176 total
Dec 4 - Dec 5
Total with taxes and fees
9.6/10 Exceptional! (250 reviews)
Lovely, relaxing stay. Well appointed and comfortable

Reviewed on Oct 24, 2025

The Captain Stannard
Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
976 Boston Post Rd Westbrook CT
$146 nightly
The price is $163 total per night from Dec 4 to Dec 5
$163 total
Dec 4 - Dec 5
Total with taxes and fees
9.8/10 Exceptional! (175 reviews)
A charming Bed and Breakfast a block from the sweetest beach. I really enjoyed my weekend here. The staff was really five stars all around.

Reviewed on Nov 7, 2025

Westbrook Inn B&B
See all 1,554 properties in Westbrook
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 Westbrook Vacation Packages

Westbrook Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
2,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Hammonasset Beach State Park, Rocky Neck State Park and Gillette Castle State Park

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Frequently asked questions

How much does a Westbrook vacation package cost?
Offering great value package deals from $500 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.