Westbrook Vacations from $669

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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.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Salt Lake City (SLC) to New Haven (HVN)
8.8/10 Excellent! (1,002 reviews)
NICE STAFF, GREEN HOTEL, GREAT BAR AND RESTAURANT.

Reviewed on Aug 1, 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Salt Lake City (SLC) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
Service was exemplary and the resort is tremendous

Reviewed on Jul 29, 2025

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
9/10 Wonderful! (1,005 reviews)
Nothing really stands out

Reviewed on Jul 28, 2025

Simsbury Inn

Simsbury Inn

3.5 out of 5
Simsbury Center
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
9.2/10 Wonderful! (258 reviews)
The Inn is conveniently situated in the center of Simsbury and looks impressive upon arrival. How, our experience was that the Inn’s promise quickly faded. An unpleasant musty odor greeted us in the hallway outside our room. The room itself showed considerable wear and tear- stained tabletop, chipped paint, missing lamp finial. The complimentary breakfast the next morning featured overcooked scrambled eggs served on paper plates with plastic cutlery. The staff, however, was very friendly and welcoming. However, on the whole our stay at the Simsbury Inn was disappointing.

Reviewed on Jul 27, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
per person
Sep 12 - Sep 14
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.6/10 Excellent! (550 reviews)
Had a great stay and the employees were top notch

Reviewed on Aug 1, 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
$284 nightly
The price is $327 total per night from Sep 1 to Sep 2
$327 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (1,008 reviews)
"So clean and beautiful really enjoy .."

Reviewed on Jul 28, 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
$250 nightly
The price is $278 total per night from Aug 13 to Aug 14
$278 total
Aug 13 - Aug 14
Total includes taxes and fees
9.6/10 Exceptional! (231 reviews)
"This is as nice a place as can be. 10 stars all the way from checkin to check out. Do not hesitate to book here"

Reviewed on Jul 25, 2025

The Captain Stannard
Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
976 Boston Post Rd, Westbrook, CT
$229 nightly
The price is $254 total per night from Sep 1 to Sep 2
$254 total
Sep 1 - Sep 2
Total includes taxes and fees
9.8/10 Exceptional! (154 reviews)
Quick business overnight
"Was very brief overnight stay during a business conference. Very clean, nice fluffy towels, cute room. Due to early checkout, I was not able to experience the breakfast, so the staff gave me a nice little take out package."

Reviewed on Apr 26, 2025

Westbrook Inn B&B
See all 1,579 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.

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Frequently asked questions

How much does a Westbrook vacation package cost?
Offering great value package deals from $669 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.