Westbrook Vacations from $751

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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.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $982, price is now $751 per person
$751
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,011 reviews)
Staff was excellent, really easy chevk in and check out.. ypu have to pay for parking every day, i think should be free for the guest..it was really noisy, you can hear the people outside , lots of sirens and ambulance noise all the time

Reviewed on Aug 20, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $2,006, price is now $1,470 per person
$1,470
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (305 reviews)
The hotel is beautiful and the grounds are wonderful. The staff was top notch. We will definitely stay again.

Reviewed on Aug 18, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $1,405, price is now $1,035 per person
$1,035
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (19 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.

Reviewed on Jun 27, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,169, price is now $866 per person
$866
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (851 reviews)
Great hotel in the niddle of town. A block from the Museum of Art. Park around thr corner..no parking on site.

Reviewed on Aug 11, 2025

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Discover the most popular places to visit in Westbrook

Westbrook Town Beach

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

Westbrook Town Beach

Tanger Outlets

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
$247 nightly
The price is $285 total per night from Sep 15 to Sep 16
$285 total
Sep 15 - Sep 16
Total includes taxes and fees
8.6/10 Excellent! (1,004 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
$252 nightly
The price is $280 total per night from Aug 21 to Aug 22
$280 total
Aug 21 - Aug 22
Total includes taxes and fees
9.6/10 Exceptional! (234 reviews)
"Wonderful"

Reviewed on Aug 19, 2025

The Captain Stannard
Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
976 Boston Post Rd, Westbrook, CT
$227 nightly
The price is $253 total per night from Sep 2 to Sep 3
$253 total
Sep 2 - Sep 3
Total includes taxes and fees
9.8/10 Exceptional! (157 reviews)
"Charming, beautiful inn; excellent food and service."

Reviewed on Aug 9, 2025

Westbrook Inn B&B
See all 1,565 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 $751 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.