Westbrook Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Westbrook

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
The price is S$376 per night from 7 Sept to 8 Sept
S$376
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Beautiful beach front property with a private beach, beachfront pool and indoor pool for raining days plus a hot tub! The terraced grounds are beautifully planted, and they have excellent service!"

Reviewed on 6 Aug, 2025

Water's Edge Resort & Spa
The Captain Stannard

The Captain Stannard

3 out of 5
138 South Main Street, Westbrook, CT
Fully refundableReserve now, pay when you stay
9.6/10 Exceptional! (231 reviews)
"This is as nice a place as can be. 10 stars all the way from checkin to check out. Do not hesitate to book here"

Reviewed on 25 Jul, 2025

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The Captain Stannard
Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
976 Boston Post Rd, Westbrook, CT
The price is S$294 per night from 2 Sept to 3 Sept
S$294
2 Sept - 3 Sept
includes taxes & fees
9.8/10 Exceptional! (155 reviews)
"My granddaughter and I had a lovely stay."

Reviewed on 31 Jul, 2025

Westbrook Inn B&B
See all 1,578 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.

Frequently asked questions

How much does a Westbrook holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday 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 book a cheap Westbrook holiday package, consider travelling in January, April and August. You'll typically find better prices on airfares and hotels during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Westbrook?
The ideal length of your Westbrook holiday depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to go to all the top sights and explore some hidden gems along the way.
Is it worth booking a holiday package to Westbrook?
Known for its views and home to popular attractions like Westbrook Town Beach, a Westbrook holiday is sure to leave an impression. Another top sight to check out? Don't miss Tanger Outlets.
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," "Traveller 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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Westbrook holiday as a package?
You can enjoy significant savings on your Westbrook break by booking a customised holiday 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 holiday 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.
How to plan a trip to Westbrook?

  1. Choose your dates: The things you plan to do in Westbrook and your preferred season can help you decide when to get away.
  2. Budget wisely: As well as the cost of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that could crop up during your trip to Westbrook.
  3. Decide how long to go away for: Now that you're more familiar with Westbrook, you can figure out the ideal length of your break. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Westbrook holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.