Westbrook Vacation Packages

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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.

Top Westbrook Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was CA $652, price is now CA $585 per person
CA $585
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8/10 Very good! (1,664 reviews)
The entire facility was extremely clean, my room included. The staff was great, no complaints whatsoever. I highly recommend this Best Western.

Reviewed on Jul 1, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $1,344, price is now CA $1,092 per person
CA $1,092
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was CA $846, price is now CA $700 per person
CA $700
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9.2/10 Wonderful! (2,191 reviews)
Excellent hotel in great location

Reviewed on Jul 1, 2026

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was CA $929, price is now CA $797 per person
CA $797
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
2/10 (1 review)
Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit.

Reviewed on Jun 2, 2026

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was CA $854, price is now CA $738 per person
CA $738
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
8.6/10 Excellent! (1,316 reviews)
Room was ok. The drains were clogged so made showering a bit difficult

Reviewed on Jun 30, 2026

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Westbrook Hotel Deals

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is CA $495 per night from Jul 8 to Jul 9
CA $495
CA $594 total
Jul 8 - Jul 9
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"we stayed for weekend had a great time beautiful room comfortable bed amazing spa tub restraunt food and bar convenient & delicious staff very nice"

Reviewed on Jun 25, 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
9.8/10 Exceptional! (82 reviews)
"Great location. Had everything we needed."

Reviewed on Jun 13, 2026

Get rates
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
The Captain Stannard

The Captain Stannard

3 out of 5
138 South Main Street Westbrook CT
The price is CA $315 per night from Jul 6 to Jul 7
CA $315
CA $350 total
Jul 6 - Jul 7
includes taxes & fees
9.8/10 Exceptional! (267 reviews)
"I loved the charm and staff would have liked a hot breakfast but their continental offering is fresh and dellicious. I would definitely stay there again."

Reviewed on Jun 24, 2026

The Captain Stannard
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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Stay near popular Westbrook attractions

Westbrook Town Beach

8.8/10 (36 reviews)
Why not spend a lazy afternoon at Westbrook Town Beach during your trip to Westbrook?
See properties

Frequently asked questions

How much does a Westbrook vacation package cost?
You'll find cheap prices from CA $585 on Expedia for your Westbrook break. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Westbrook costs.
What are the cheapest months to go to Westbrook?
January, April and August are great times to search for cheap Westbrook vacation packages. Travelling in quieter months means you can usually find lower prices on hotels and flights.
How many days is enough for Westbrook?
With around 2 days, you'll have plenty of time to enjoy popular neighbourhoods like Westbrook Centre and Saybrook Manor during your Westbrook vacation. Be sure to also add Clinton Crossing Premium Outlets and Hammonasset Beach to your sightseeing itinerary. Looking for more adventures? Consider exploring outside of Westbrook on tours and day trips.
Is it worth booking a vacation package to Westbrook?
Boasting a host of highlights starting with its top-notch views, Westbrook is a good vacation destination. Whether you'd like to check out attractions like Westbrook Town Beach and Tanger Outlets or take the road less travelled, you'll have loads to see and do on your Westbrook vacation.
How to find the best Westbrook package deals?
Finding a cheap Westbrook package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add some filters and see what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Westbrook package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Westbrook vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations separately. Better still, you can personalize your Westbrook trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Westbrook?
If you've got your Westbrook travel dates finalized, book as early as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Westbrook?

  1. Choose your travel dates: The things you want to do in Westbrook and your favourite season will help you decide when to get away.
  2. Budget wisely: In addition to the price of your hotel, you'll need to factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Westbrook.
  3. Decide your trip length: Think about how much time you want to spend exploring Westbrook. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Westbrook vacation package.

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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.