Westport Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Marina Timo

Top hotels in Westport

Inn at Longshore

Inn at Longshore

2.5 out of 5
260 Compo Rd S, Westport, CT
9/10 Wonderful! (161 reviews)
a unique experience
"A classic old inn on spectacular grounds with waterfront lawn and views . Surrounded by a golf course. They have a wonderful modern restaurant attached with great food and stunning water views named La Plage . Excellent service , outdoor and indoor seating really a gem !! The inn has quirks but for ..."

Reviewed on 20 Aug 2025

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Inn at Longshore
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
8.4/10 Very Good! (1,644 reviews)
"Patrick at the front desk was very accommodating and helpful with whatever we needed. The bed was comfy. A little noisy from the street and the train nearby but the actual hotel was quiet. A good stay for the price."

Reviewed on 24 Aug 2025

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Amsterdam Hotel
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln, Trumbull, CT
Fully refundableReserve now, pay when you stay
The price is 4.005.656 ₫ per night from 7 Sept to 8 Sept
4.005.656 ₫
4.606.505 ₫ total
7 Sept - 8 Sept
includes taxes & fees
8/10 Very Good! (1,005 reviews)
"Excellent stay."

Reviewed on 22 Aug 2025

Trumbull Marriott Shelton
See all 1,068 properties in Westport
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

Compo Beach

Compo Beach

Why not spend a care-free afternoon at Compo Beach during your travels in Westport? Stroll along the seaside or experience the area's art scene.

Compo Beach

Levitt Pavilion

You can enjoy a show at Levitt Pavilion during your trip to Westport. While you're in the area, stroll along the beautiful beaches.

Levitt Pavilion

Burying Hill Beach

If a restful holiday is part of your travel plans, Burying Hill Beach might be the perfect place to visit during your trip to Westport. Stroll along the waterfront or discover the area's sunsets.

Burying Hill Beach

Frequently asked questions

How much does a Westport holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. However, how much your holiday to Westport costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Westport?
February, June and August are the best times to look for cheap Westport holiday packages. Opting to travel in quieter months means you can generally find better prices on hotels and flights.
How many days is enough for Westport?
We recommend booking a Westport holiday for a minimum of 2 days. This will give you enough time to check off popular sights such as Burying Hill Beach and Alvord Beach, as well as check out neighbourhoods like Cranbury and Greens Farms. You might even be able to slot in a day trip or two from Westport.
Is it worth booking a holiday package to Westport?
Westport has all the ingredients you need for a fantastic getaway — golfing, history and nature are just the start. Whether you'd like to check out attractions like Compo Beach and Levitt Pavilion, or venture off the beaten track, you'll find plenty to experience on your Westport holiday.
How to find the best Westport package deals?
Start your search for a Westport package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Westport package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Westport escape off to a flying start.
Is it cheaper to book a Westport holiday as a package?
You can enjoy significant savings on your next Westport escape by booking a customised holiday package. Check the "Package" heading, then enter your destination and travel dates to view some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Westport?
If you're planning an impromptu Westport holiday, 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 find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Westport?

  1. Choose your travel dates: The things you'd like to do in Westport and your favourite season can help you decide when to travel.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Westport. Then, pick a hotel that suits your budget, whether that's an affordable stay or a lavish getaway.
  3. Determine how many days away: Start by making a list of all the activities and attractions you want to experience in Westport. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Westport holiday package that brings all your bookings together.