Westport Holidays

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Top hotels in Westport

Delamar Westport

Delamar Westport

1595 Post Rd E Westport CT
4.519.615 ₫
5.717.278 ₫ total
27 Sept - 28 Sept
includes taxes & fees
Delamar Westport
Amsterdam Hotel

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT
Fully refundableReserve now, pay when you stay
2.260.782 ₫
2.623.806 ₫ total
18 Oct - 19 Oct
includes taxes & fees
Amsterdam Hotel
Hyatt Regency Greenwich

Hyatt Regency Greenwich

1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
5.067.270 ₫
5.827.361 ₫ total
18 Oct - 19 Oct
includes taxes & fees
Hyatt Regency Greenwich
See all 1,106 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.

Stay near popular Westport attractions

Compo Beach

9.6/10 (20 reviews)
This 29-acre shoreline park offers pristine sandy beaches and stunning views of Long Island Sound. Enjoy swimming, volleyball, or simply relax on the boardwalk while watching sailboats drift across the horizon.
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Levitt Pavilion

10.0/10 (7 reviews)
Nestled along the Saugatuck River, this outdoor venue has offered free summer concerts since 1974. Bring a picnic blanket and enjoy diverse musical performances under the stars.
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Westport Country Playhouse

9.8/10 (6 reviews)
This historic theatre, converted from an 1835 tannery, presents acclaimed productions in an intimate setting. Enjoy performances in a venue blending historic charm with modern comfort.
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Westport Farmers Market

9.6/10 (5 reviews)
The Westport Farmers' Market offers 50+ vendors selling non-GMO, local produce and artisanal goods since 2006. Enjoy live music while browsing colourful stalls of fresh fruits, vegetables, and gourmet foods.
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Burying Hill Beach

10.0/10 (3 reviews)
This serene shoreline park offers a tranquil mix of sandy and rocky beach areas along Long Island Sound. Enjoy picnicking at tables overlooking the wildlife area or explore the coastal landscape at your leisure.
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Old Mill Beach

10.0/10 (5 reviews)
Why not spend a lazy afternoon at Old Mill Beach during your trip to Westport? Wander the waterfront or discover the area's sunsets.
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Alvord Beach

8.8/10 (3 reviews)
Tucked within Sherwood Island State Park, Alvord Beach offers a serene Connecticut shoreline with picturesque coastal views. Enjoy swimming in clear waters or a leisurely picnic against the backdrop of Long Island Sound.
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Westport Arts Center

Enjoy an outing to Westport Arts Center during your stay in Westport. Wander the waterfront or discover the area's sunsets.
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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.