Westbrook Vacations from $421

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 $616, price is now $421 per person
$421
per person
Jun 25 - Jun 28
found 2 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
8.6/10 Excellent! (1,005 reviews)
Did valet parking which excellent

Reviewed on Apr 11, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,445, price is now $1,364 per person
$1,364
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
No reviews
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,083, price is now $769 per person
$769
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.4/10 Exceptional! (349 reviews)
The hotel was perfect for a one night getaway. Matthew at the front desk was wonderful, and so very helpful. The dinner was outstanding, as was the breakfast the next morning. The location on the beach was perfect, and even though it was April, we enjoyed a nice walk on the beach. Would definitely come back!

Reviewed on Apr 12, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,389, price is now $1,032 per person
$1,032
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.2/10 Wonderful! (30 reviews)
Great stay with many amenities to enjoy within the building!

Reviewed on Apr 3, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $887, price is now $665 per person
$665
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
9.2/10 Wonderful! (968 reviews)
Wonderful stay as always. Great Location close to Yale, wonderful staff and a great lobby to enjoy coffee and do work.

Reviewed on Apr 9, 2026

Don't see what you're looking for?
See all available trips from Columbus to Westbrook
View all trips

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(186 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
Fully refundableReserve now, pay when you stay
$266 nightly
The price is $305 total per night from Apr 26 to Apr 27
$305 total
Apr 26 - Apr 27
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
Beautiful property on the water! Loved it! Only problem was the noisy air handler!

Reviewed on Apr 12, 2026

Water's Edge Resort & Spa
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

Westbrook CT
Get rates
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
976 Boston Post Rd Westbrook CT
$213 nightly
The price is $237 total per night from May 12 to May 13
$237 total
May 12 - May 13
Total with taxes and fees
9.8/10 Exceptional! (186 reviews)
Breakfast was amazing! Staff was so kind, and place was very clean.

Reviewed on Apr 9, 2026

Westbrook Inn B&B
See all 1,549 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Westbrook vacation package cost?
Offering great value package deals from $421 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.

Explore a world of travel with Expedia

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