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.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Save 100% on your flight
Price was $628, price is now $487 per person
$487
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (862 reviews)
Booking my next stay now!

Reviewed on Aug 24, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,637, price is now $1,607 per person
$1,607
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
No reviews
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 $1,170, price is now $867 per person
$867
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (861 reviews)
I had a great time at the Graduate. Quiet, close to campus, close to Toad's place, and close to bunch of great restaurants. Only area of improvement would be the WiFi -- it was consistent but not particularly fast.

Reviewed on Aug 25, 2025

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 $1,385, price is now $1,047 per person
$1,047
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,008 reviews)
Very loud due to multiple bars and clubs right out side the hotel but that’s the only negative. It’s in a good location, with a lot to do around, which is why it’s loud in the area. Place is very nice and clean. Great security and easy to find parking.

Reviewed on Aug 24, 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
$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
See all 1,572 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 $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.