Westbrook Vacation Packages 2025/2026 from $385

Name: Sound View Greenport
Price range: $279 total

Westbrook flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Residence Inn by Marriott Hartford/Windsor

$385

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Sarasota (SRQ) to New Haven (HVN)

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Beechmont - Perfect for Family Retreat!

Save 100% on your flight

$798

per person

Jan 9 - Jan 11

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to New Haven (HVN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.

Hilton Garden Inn Hartford North/Bradley Int'l Airport

$436

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Sarasota (SRQ) to New Haven (HVN)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy free perks like free self parking and an area shuttle.

Cambria Hotel Manchester South Windsor

$539

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Sarasota (SRQ) to New Haven (HVN)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Simsbury Inn

Simsbury Center

$1,188

per person

Dec 26 - Dec 31

found 4 hours ago

Roundtrip flight included

Charlotte (CLT) to New Haven (HVN)

This smoke-free hotel includes 3 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the sauna and free perks like buffet breakfast and free self parking.

Top Westbrook hotels deals

Water's Edge Resort & Spa

1525 Boston Post Road, Westbrook, CT

Free Cancellation

Reserve now, pay when you stay

$228 nightly

$263 total

Nov 2 - Nov 3

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.

Westbrook Inn B&B

976 Boston Post Rd, Westbrook, CT

$209 nightly

$233 total

Oct 27 - Oct 28

Total with taxes and fees

This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace, a garden, and a snack bar/deli are also on offer.

The Captain Stannard

138 South Main Street, Westbrook, CT

Free Cancellation

Reserve now, pay when you stay

$236 nightly

$263 total

Nov 25 - Nov 26

Total with taxes and fees

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A terrace, a garden, and a picnic area are also on offer.

Motel 6 New Haven - Branford, CT

320 E Main St, Branford, CT

Free Cancellation

$74 nightly

$85 total

Nov 3 - Nov 4

Total with taxes and fees

A restaurant, free self parking, and a 24-hour front desk are among this motel's amenities. WiFi in public areas is free. A snack bar/deli is also provided.

Red Roof Inn Meriden

10 Bee St, Meriden, CT

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$114 total

Oct 27 - Oct 28

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out. There's a gym and multilingual staff can provide around-the-clock assistance.

Sound View Greenport

58775 County Rd 48, Greenport, NY

$244 nightly

$279 total

Nov 9 - Nov 10

Total with taxes and fees

A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.

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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.

Popular places to visit

Westbrook Town Beach

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

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.

Frequently asked questions

How much are vacation packages to Westbrook?

Travelocity offers flight and hotel vacation packages starting from just $385. With these kinds of deals, you'll be saying hello to Westbrook before long.

How long should my Westbrook vacation be?

Many travelers pack their suitcase and vacation in Westbrook for approximately 2 nights. That gives you a rough guide, but don't feel limited by it. Whether you only stay for a few days to see the famous attractions or hang around to uncover hidden treasures, an amazing adventure awaits.

Where can I get the best vacation package deals for Westbrook?

You'll find amazing Westbrook package deals with Travelocity. Select from as many as 400 air carriers and 1,000,000 worldwide properties and turn those travel dreams into a reality.

Why should I purchase my Westbrook vacation package with Travelocity?

We make traveling the world easy. Whether you're searching for an amazing new place to wander around or want to ensure you get the best deal around, we're here to help. Our 24/7 customer support, high-quality service and Price Match Guarantee mean you can book with confidence.

Can I save money on my Westbrook car rental if I combine it with my hotel or flight?

Certainly — combine your car, hotel and flight into a Westbrook vacation package and you can save a ton. With so many things to do in and around Westbrook, having your own ride will more than come in handy. Once you've settled into the driver's seat, turn up the tunes and head to Times Square, a renowned sight approximately 90 mi from Westbrook.

Which airport is best for Westbrook?

Bradley Intl. Airport (BDL) (45 mi away from the downtown area), T.F. Green Airport (PVD) (60 mi away from central Westbrook) and MacArthur Airport (ISP) (50 mi away from central Westbrook) are all great options for Westbrook.

What is there to do in Westbrook?

You'll notice a certain kind of magic as you stroll the streets of Westbrook. Westbrook Town Beach and Tanger Outlets are just two famous attractions that lure visitors to this fantastic city, so put them on your list of places to see.

Where should I stay when visiting Westbrook?

Many travelers choose to check in to the Waters Edge Resort & Spa. It's the perfect base for your Westbrook vacation.