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Westport holiday lettings

We found 492 holiday rentals — enter your dates for availability

Discover a selection of 58 homes and other holiday rentals in Westport that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include parking and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Westport

Showing deals for:6 Mar - 13 Mar

Image gallery for Updated Farmhouse Retreat

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10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Updated Farmhouse Retreat

Wilton, CT

8% off
Price is £7,571
for 7 nights, 1 room
£1,082 per night
includes taxes & fees
Updated Farmhouse Retreat

Find spaces that suit your style

Why visit Westport

  • Stunning beaches: Westport boasts beautiful beaches ideal for sunbathing, swimming, and relaxing by the shore.
  • Picturesque parks: Enjoy recreational activities and scenic walks in Westport's charming urban parks.
  • Cultural experiences: Explore the town's historical sites and vibrant arts scene, catering to diverse interests.
  • Family-friendly attractions: Discover a variety of activities perfect for families, ensuring fun for all ages.
  • Unique accommodations: Choose from a range of delightful holiday rentals, from cosy cottages to stylish apartments.

Popular types of accommodation in Westport

Discover the charm of Westport with our exceptional holiday rentals, ranging from houses and cosy cottages to stylish apartments. Whether you’re seeking a peaceful retreat or a base for adventure, Westport accommodation offers something for every traveller. Explore our variety of holiday cottages and rentals, designed to provide transparency, savings, and reassurance for your perfect getaway.

  • Houses: The top choice among visitors to Westport, offering spacious and comfortable living for families or groups seeking a home-away-from-home experience.
  • Apartments: A popular option for those who prefer a self-contained space, providing convenient access to local amenities.
  • Cottages: These delightful, quaint retreats offer a charming escape for couples or small families looking for a peaceful getaway.
  • Cabins: Ideal for outdoor enthusiasts, these rustic lodgings provide a cosy haven amidst nature.
  • Condos: A practical choice for visitors, offering modern comforts and communal facilities in a vibrant setting.**

Top attractions in and around Westport

Westport, Connecticut, is an ideal destination for outdoor enthusiasts, families, and couples alike. With its stunning beaches, picturesque urban parks, and modern universities, there's plenty to explore. Visitors can enjoy a variety of activities that cater to those seeking outdoor adventures, family fun, and cultural experiences. Make the most of your time in Westport and discover its charming attractions.

  • Compo Beach: A delightful seaside escape right in Westport, Compo Beach offers a stunning shoreline, perfect for sunbathing, swimming, and picnicking. With its vibrant beach vibes, it’s an ideal spot for relaxation or a stroll along the sandy shores.
  • Fairfield University: Located 3.1km from Westport, this modern university boasts impressive architecture and a lively atmosphere, embodying city vibes. The campus is a beautiful space for a leisurely walk, featuring art installations and green areas.
  • Historic South Norwalk: Just 2.5km away, Historic South Norwalk is rich in culture, showcasing charming 19th-century architecture, boutique shops, and delightful eateries. This area invites exploration and appreciation of its vibrant history.

Things to do recommended for couples

Looking for a romantic getaway in Westport? Enjoy an evening at the Levitt Pavilion for a delightful music concert. For a touch of romance, visit Harmony Vineyards or Del Vino Vineyards, both just a short drive away, offering exquisite wines and charming atmospheres.

Things to do recommended for families

Families can enjoy a thrilling experience at the Hartford HealthCare Amphitheater, just 5.6km away, or unwind at Seaside Park, 5.0km away, for some wellness and relaxation. Don't miss the Rolnick Observatory in Westport for an entertaining family outing under the stars.

Things to do recommended for groups

In Westport, groups can enjoy a captivating performance at the Westport Country Playhouse, savour fresh produce at the vibrant Farmers Market, and indulge in shopping and entertainment at the nearby Center Seven Shopping Centre, just a short drive away, ensuring a delightful local experience.

What do I need to keep in mind when booking a vacation in 'Westport

If you're travelling with a group, family, or pets, or if you're seeking extended stays, be sure to refine your search according to your key priorities. Here are some helpful tips for booking with Vrbo.

  • Traveling to Westport with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can refine your search for all of these options, and more, on Vrbo.
  • Traveling to Westport with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, like a private swimming pool. Additionally, it would be wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Westport: For many families, a holiday wouldn't feel complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel completely at home.
  • Planning for a long term stay visiting Westport: If you're in search of holiday rentals with offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. You might also want to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Westport

Westport, Connecticut, offers a delightful blend of outdoor activities, family-friendly attractions, and romantic spots perfect for a getaway. With easy access to central Westport, visitors can explore charming neighbourhoods that radiate warmth and friendliness. Whether enjoying picturesque parks or delving into the town's historical sites, you'll find it an ideal location for families and couples alike. Discover the unique vibes and experiences that make Westport a memorable destination.

  • Stamford: Stamford is a vibrant city located 6.8km from Westport, offering a delightful mix of family-friendly activities and urban charm. Visitors can enjoy an array of shopping options, from boutique stores to major retailers, as well as a variety of entertainment venues, including theatres and cultural centres. The city’s landmarks, such as the bustling Stamford Town Center and the scenic modern square, provide ample opportunities for exploration and relaxation, making it an ideal destination for a day trip or a leisurely afternoon.
  • Norwalk: Situated a mere 1.9km from Westport, Norwalk is a lovely city that caters to families and outdoor enthusiasts alike. The city is known for its beautiful beaches, including the popular family beach, where visitors can bask in the sun or enjoy water activities. Norwalk also boasts a rich history, with several historic sites to explore, alongside a vibrant shopping district. With educational attractions and seasonal skiing options, Norwalk offers a well-rounded experience for all ages.
  • Fairfield: Fairfield, located 3.1km from Westport, is a charming city that combines culture and outdoor enjoyment. The city features a mix of recreational areas, shopping districts, and educational institutions, including a modern college university. Visitors can relax on the sandy shores of the beach or explore the family-friendly beach area, making it a perfect spot for both relaxation and adventure. The emphasis on culture and community makes Fairfield a delightful place to visit.

Best time to go to Westport

If you're planning a trip to Westport, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April to May and July, while off-peak times, like January to February and October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.5°F (-0.3°C)Light RainMostly SunnySlightly LowSlightly Low
February32.7°F (0.4°C)Light RainMostly SunnySlightly LowSlightly Low
March39.2°F (4.0°C)Light RainMostly SunnyAverageSlightly Low
April49.5°F (9.7°C)Light RainMostly SunnySlightly HighAverage
May59.4°F (15.2°C)Light RainMostly SunnySlightly HighAverage
June68.4°F (20.2°C)Light RainMostly SunnyAverageSlightly High
July75.4°F (24.1°C)Light RainMostly SunnySlightly HighSlightly High
August74.1°F (23.4°C)Light RainMostly SunnyAverageSlightly High
September67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
October57.4°F (14.1°C)Light RainMostly SunnySlightly LowAverage
November45.9°F (7.7°C)Light RainMostly SunnyAverageAverage
December37.9°F (3.3°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you aiming to save on your upcoming getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy considerable savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated area to plan new adventures, pick up from where you last stopped, or review and arrange your itinerary. You can easily access properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The waterfront setting of Westport is ready to explore

Take a holiday to Westport and enjoy the area's opera, entertainment and theatre scene. This city is well-known for its football games and restaurants. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Westport

Are you looking for top things to see and do during your stay? Venture out of your cosy holiday rental and experience everything that makes Westport a one-of-a-kind holiday spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Norwalk Maritime Aquarium (4.2 mi / 6.7 km)
  • Chelsea Piers (10.2 mi / 16.4 km)
  • Beardsley Zoo (10.4 mi / 16.7 km)
  • Hand & Stone Massage and Facial Spa (11.1 mi / 17.8 km)
  • Stanwich Club (14 mi / 22.5 km)
  • Del Vino Vineyards (15.9 mi / 25.6 km)

Exploring the natural features in Westport

Whether you're looking for adventure or just want to spend some time taking in the scenery, Westport is a great place to get outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Compo Beach (2.6 mi / 4.2 km)
  • Southport Beach (3.3 mi / 5.4 km)
  • Calf Pasture Beach (4.2 mi / 6.7 km)
  • Fairfield Beach (5.5 mi / 8.9 km)
  • Penfield Beach (6.1 mi / 9.8 km)
  • Jennings Beach (6.3 mi / 10.1 km)

Transport options to and around Westport

The nearest airport is in Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), located 11.9 mi (19.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 17.3 mi (27.8 km) away.

If you're travelling by train, make your way to Westport Station or Green's Farms Station to see more of the city.

Frequently asked questions

What is the best area to stay in Westport when booking a holiday rental?
When considering a holiday rental in Westport, Connecticut, the Saugatuck neighbourhood is an excellent choice. This vibrant area is known for its picturesque waterfront, charming shops, and delightful dining options. Staying here allows you to enjoy the scenic views along the Saugatuck River, and you can easily visit the nearby Levitt Pavilion for the Performing Arts, which hosts a variety of live events during the summer months.

Another appealing option is the Compo Beach area, renowned for its stunning beach and recreational facilities. This location is superb for families and beach lovers alike, offering a range of activities such as swimming, picnicking, and beach volleyball. The proximity to the Westport Country Playhouse, a regional theatre known for its excellent productions, adds to the cultural allure of this neighbourhood.
How much does it cost to rent a holiday home in Westport?
Prices for holiday rentals in Westport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Westport to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Westport holiday house rentals?
You can find great discounts on house rentals in Westport on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Westport?
For renting a beach house in Westport, Connecticut, consider the picturesque shoreline along Compo Beach, which is a popular destination for both locals and visitors. This area offers a variety of holiday rentals, including charming cottages and modern homes that often feature amenities like outdoor decks, spacious living areas, and fully equipped kitchens, superb for family gatherings or relaxing retreats. Many properties in this vicinity provide easy access to the sandy beach, where families can enjoy swimming, sunbathing, and picnicking.

Another appealing neighbourhood is the Saugatuck area, known for its vibrant waterfront and quaint shops. Here, you can find beach houses that typically include amenities such as private patios, barbecue grills, and sometimes even access to community pools. The proximity to local cafes and restaurants adds to the convenience, allowing travellers to enjoy fresh seafood and local delicacies without needing to venture far.
What is the most popular type of holiday rental accomodation in Westport?
In Westport, holiday houses are the most popular type of rental accommodation, with around 38 available throughout the area. These houses often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces like patios or gardens, making them ideal for families or groups seeking comfort and privacy. Additionally, there are several apartments and cottages available, which provide a more compact and homely feel, often including amenities such as kitchen facilities and cosy living areas.
Are there any family house rentals in Westport?
In Westport, Connecticut, there is a wide selection of family-friendly house rentals, with around 32 available throughout the area. This charming coastal town offers a superb blend of suburban tranquillity and access to various recreational activities. Many of these properties boast spacious living areas, fully equipped kitchens for family meals, and outdoor spaces like gardens or patios, ideal for children to play.
Can I rent a holiday home with a pool or hot tub in Westport?
In Westport, Connecticut, there are several holiday homes available for rent that come with pools or hot tubs, with around 11 options to choose from. This picturesque coastal town offers a variety of neighbourhoods, including the charming Saugatuck area, which is known for its beautiful waterfront views and proximity to local shops and restaurants.
Can I find long-stay holiday rentals in Westport?
A long-stay holiday rental in Westport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Westport?
In Westport, there are several pet-friendly house rentals available, with around 21 options to choose from. These rentals typically offer a range of amenities, including spacious backyards, fully equipped kitchens, and comfortable living spaces, making them suitable for families and groups travelling with pets.

The area is known for its picturesque coastal views and access to several parks, such as Winslow Park and the expansive Compo Beach, both of which provide plenty of opportunities for outdoor activities with furry companions. Compo Beach, in particular, is a popular spot where pets can enjoy the sandy shores, especially during the off-season.
Are there any remote work holiday rentals in Westport?
In Westport, Connecticut, there is a solid selection of remote work holiday rentals available, with around 33 properties suited for those looking to blend work and leisure. Many of these rentals come equipped with essential amenities for a productive work environment, including dedicated office spaces, desk chairs, and computer monitors. High-speed Wi-Fi is typically provided, ensuring seamless connectivity for virtual meetings or remote tasks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Westport holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Westport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Westport?
In Westport, popular holiday rental amenities include fully equipped kitchens, which typically feature essentials such as microwaves, dishwashers, and refrigerators. These conveniences allow guests to prepare their own meals and enjoy the comfort of home during their stay. Many properties are designed with modern furnishings and open living spaces, fostering a friendly setting for families or groups.
When is the best time to visit Westport for a holiday rental?
The best time to book a holiday rental in Westport is during the peak season from May to July, with July being the most popular month. This vibrant period is great for those looking to enjoy the coastal charm and outdoor activities that Westport has to offer. With warm temperatures averaging around 27°C, visitors can indulge in everything from beach days to picnics in the scenic parks.

During these months, the town flourishes with a lively atmosphere, making it an ideal time for families and friends to gather. You'll find plenty of opportunities for water sports, hiking along picturesque trails, and exploring local shops and cafes. The summer months also bring a variety of events and festivals, creating a great blend of relaxation and entertainment.

If you're looking for a more budget-friendly option, consider visiting in October. This shoulder month offers a quieter experience, where you can enjoy the beautiful autumn scenery as the leaves transform into a stunning palette of colours. The comfortable temperatures, usually in the mid-teens Celsius, allow for pleasant strolls along the waterfront and visits to local attractions without the summer crowds.
How early should I book a Westport holiday rental?
Book your Westport holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Westport?
In Westport, visitors can enjoy a variety of attractions that showcase the town's charm and coastal beauty. The picturesque Compo Beach offers sandy shores and recreational activities, ideal for families and those looking to relax by the water. Nearby, the Westport Country Playhouse provides a rich cultural experience with its diverse theatrical productions, making it a great spot for arts enthusiasts.

The charming downtown area features a selection of boutique shops and eateries, great for leisurely strolls and enjoying local cuisine. For nature lovers, the scenic Saugatuck River offers opportunities for kayaking and fishing, while the nearby Aspetuck Land Trust preserves beautiful trails for hiking and exploring.
Can I change or cancel my Westport home rental booking on Vrbo?
To find Westport holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Westport holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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