Westport holiday lettings

We found 500 holiday rentals — enter your dates for availability
Discover a selection of 54 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:18 Dec - 25 Dec

Image gallery for Fairfield Beach Modern Colonial

View of back of house
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
Price is £6,699
for 7 nights, 1 home
£957 per night
includes taxes & fees
Fairfield Beach Modern Colonial

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Why visit Westport

  • Scenic Beaches: Relax on Westport's picturesque beaches, perfect for sunbathing and enjoying coastal views.
  • Charming Streets: Stroll through delightful streets lined with boutique shops and inviting cafes for outdoor seating.
  • Urban Parks: Explore tranquil parks that offer a serene escape amidst nature’s beauty.
  • Cultural Experiences: Engage with the vibrant local arts scene and visit engaging museums.
  • Cozy Accommodations: Enjoy a variety of charming vacation rentals, from private homes to cosy cottages.

Popular types of accommodation in Westport

Planning a getaway to Westport, Connecticut? You're in for a treat. This charming coastal town offers a delightful array of vacation rentals, from private homes to cosy cottages. Enjoy the picturesque waterfront, explore scenic parks, or indulge in the vibrant local arts scene. With options like riverfront accommodations, Westport invites you to experience its unique blend of tranquillity and culture. Discover the perfect base for your adventures in this beautiful part of the United States.

  • Houses: The top choice for visitors, offering spacious and comfortable living for families or groups seeking a home-like atmosphere.
  • Apartments: A popular option for those looking for convenience and modern amenities, perfect for a city-style stay.
  • Cottages: Charming and quaint, these are ideal for a peaceful retreat with a touch of rustic charm.
  • Cabins: A favourite for nature lovers, providing a cosy escape amidst the beautiful surroundings.
  • Condos: Stylish and often centrally located, these are great for those wanting a blend of comfort and convenience.**

Top attractions in and around Westport

Westport, Connecticut, is a charming destination perfect for outdoor enthusiasts and those seeking a romantic getaway. With its picturesque beaches, urban parks, and engaging museums, visitors can enjoy a variety of experiences that blend culture and family fun. Whether you're strolling along the scenic coastline or exploring local attractions, Westport offers a delightful escape for all types of travellers.

  • Compo Beach: A beautiful sandy beach perfect for sunbathing, swimming, and picnicking. Enjoy the stunning coastal views and vibrant beach vibes, with facilities for sports and relaxation.
  • Historic South Norwalk: A charming area rich in history and culture, featuring unique architecture, galleries, and delightful eateries. Explore the local heritage and vibrant arts scene.
  • The Glass House: A remarkable museum that showcases modern architecture and design. Experience the seamless integration of nature and art within its stunning glass structure.

Things to do recommended for couples

For a romantic getaway in Westport, explore the scenic beauty of Compo Beach at sunset, indulge in a wine tasting at a local vineyard, or enjoy a candlelit dinner at an intimate restaurant. Don’t forget to stroll along the charming Main Street, filled with quaint shops and cafes.

Things to do recommended for families

Families can explore the beautiful Compo Beach, perfect for swimming and picnics, or visit the Westport Country Playhouse for captivating performances. Don't miss the charming shops and eateries in downtown Westport, offering delightful local flavours and unique finds for all ages.

Things to do recommended for groups

Groups visiting Westport can experience thrilling outdoor adventures at The Adventure Park at Discovery Museum, an exhilarating zipline ropes course situated 13km from the town. It's perfect for those seeking excitement and a chance to connect with nature.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're travelling with a group, family, pets, or seeking extended stays, it's important to prioritise your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Westport with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all of these options, and more, on Vrbo.
  • Traveling to Westport with young kids: Travelling with young children can present its challenges. It’s important to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Westport: For many, a family holiday isn’t truly complete without their four-legged companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel at home.
  • Planning for a long term stay visiting Westport: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Westport

Westport, Connecticut, offers a delightful blend of outdoor adventures and serene landscapes, perfect for a romantic getaway or a family-friendly holiday. Stroll along the picturesque streets, where charming boutiques and cafes invite outdoor seating. Explore the natural beauty of the area's parks and beaches, providing a tranquil escape. With its friendly atmosphere and sunny weather, Westport is an ideal destination for those seeking relaxation and scenic experiences.

  • Stamford: Stamford is a vibrant city located 18km from Westport, offering a delightful mix of urban attractions and outdoor experiences. Visitors can enjoy a variety of shopping options, from high-end boutiques to popular retail chains in the bustling downtown area known as the Stamford Town Center. The city is also home to the Palace Theatre, which showcases an array of performances including concerts and plays. The picturesque waterfront offers scenic views and walking paths, making it a great spot for a leisurely stroll or family outing.
  • Norwalk: Only 5km away from Westport, Norwalk is a charming city that caters to families and outdoor enthusiasts alike. One of its highlights is the beautiful beaches, perfect for a day of sun and sand. The city is also home to the Maritime Aquarium, where visitors can explore marine life and learn about conservation. Shopping options abound, with various local shops and eateries lining the streets. Moreover, Norwalk offers access to picturesque parks and golf courses, making it an ideal destination for both relaxation and recreation.
  • Bridgeport: Located 14km from Westport, Bridgeport is known for its lively atmosphere and diverse attractions. The city boasts an impressive array of recreational facilities, including the Beardsley Zoo and the Bridgeport Bluefish baseball stadium. Families can enjoy a day at the beach, or take in a show at the Arena at Harbor Yard, which hosts concerts and sporting events. With its rich history and vibrant community, Bridgeport provides a delightful experience for visitors looking to soak up local culture and outdoor activities.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 a breeze

Are you hoping to cut costs on your next journey? It might be worth considering flexibility with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect 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 Trip Board provides a convenient area for you to plan new trips, refine your existing arrangements, or review and manage your bookings. Your saved or reserved properties are neatly organised into categories: Potential, Upcoming, and Current Trips. To discover more about Trip Boards, please 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)
  • Del Vino Vineyards (15.9 mi / 25.6 km)
  • Country Club of Fairfield (4.5 mi / 7.2 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)
  • 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)
  • Lake Mohegan (7.1 mi / 11.4 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 charming neighbourhood of Saugatuck is often regarded as an excellent choice. This vibrant area is known for its picturesque waterfront, with the Saugatuck River weaving through, offering a delightful backdrop for leisurely strolls. Visitors can enjoy the local boutique shops, cosy cafes, and a selection of restaurants that cater to diverse tastes.

Another appealing neighbourhood is the Old Hill area, characterised by its serene residential atmosphere and lush, green spaces. This area is particularly close to the Westport Country Playhouse, a renowned venue for live performances, and the scenic Compo Beach, which provides a superb spot for sunbathing, swimming, and enjoying beautiful sunsets.
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, the area around Compo Beach is highly desirable. This picturesque beach features beautiful sandy shores and scenic views of Long Island Sound, making it an ideal spot for beach house rentals. Properties here typically include amenities such as spacious outdoor decks, private beach access, and modern kitchens, great for family gatherings or entertaining guests.

Additionally, the Saugatuck area, with its charming waterfront and proximity to local restaurants and shops, offers a variety of rental options. Many houses in this neighbourhood come with features like outdoor showers, patio spaces with grills, and easy access to boating and water sports. The Saugatuck River adds to the appeal, offering opportunities for kayaking and paddleboarding right from your doorstep.

Furthermore, the nearby Longshore Club Park provides a lovely setting for outdoor activities, including picnicking and walking trails, enhancing the beachside experience. Rentals in Westport often reflect a blend of comfort and convenience, allowing travellers to enjoy both the beach and the vibrant local culture.
What is the most popular type of holiday rental accomodation in Westport?
In Westport, holiday houses are the most popular type of holiday rental, with around 152 available throughout the area. These properties are typically spacious and are often situated in peaceful neighbourhoods, making them ideal for families or groups seeking a relaxing getaway. Most holiday houses come equipped with multiple bedrooms, full kitchens, and outdoor spaces such as gardens or patios, superb for enjoying the lovely Connecticut weather. Additionally, there are about 20 apartments and 16 cottages available, providing more compact options for solo travellers or couples.
Are there any family house rentals in Westport?
In Westport, Connecticut, there is a solid selection of family-friendly house rentals, with around 32 options available. This charming coastal town offers a variety of properties that cater to families, particularly in neighbourhoods like Saugatuck and Compo Beach. Many of these homes boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for kids to play and explore.

Visitors can expect amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay. The proximity to local attractions, including the beach and parks, provides ample opportunities for outdoor activities and family outings. Westport's vibrant community features beautiful waterfronts, picturesque walking trails, and a rich arts scene, making it an excellent destination for families seeking both relaxation and adventure.
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 feature pools or hot tubs, with around 14 options to choose from. This picturesque coastal town offers a charming blend of seaside beauty and suburban tranquillity, making it an excellent choice for a relaxing getaway.

Travellers can expect amenities such as private swimming pools, inviting hot tubs, spacious outdoor patios for sunbathing or dining al fresco, and fully equipped kitchens that cater to all your culinary needs. Many properties are also designed with families in mind, featuring large living areas and multiple bedrooms to accommodate groups comfortably.

Westport's proximity to the beach adds to the allure, and visitors can enjoy nearby parks and waterfront activities.
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, offering a range of amenities that cater to both travellers and their furry companions. Many of these properties feature spacious layouts with modern kitchens, outdoor spaces such as private gardens or decks, and comfortable living areas ideal for relaxation after a day of exploring.

The neighbourhood provides easy access to local parks, which are superb for walking pets and enjoying the outdoors. Notable spots include Winslow Park, where you can find walking trails and picnic areas, and the scenic Compo Beach, which is also welcoming to pets during certain hours.
Are there any remote work holiday rentals in Westport?
In Westport, Connecticut, there are numerous options for remote work holiday rentals, with around 144 properties available. These rentals cater well to those needing a workspace, featuring amenities such as dedicated desks, ergonomic chairs, and reliable Wi-Fi for seamless connectivity. Many properties also offer free internet access, ensuring that you can stay productive during your stay.

The charming town of Westport is known for its scenic coastal views, local parks, and vibrant arts scene, providing a pleasant backdrop for both work and leisure. After hours, you can explore the nearby beaches, enjoy the waterfront dining, or visit the local shops and galleries. 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 rental amenities include kitchens that allow for convenient meal preparation, fireplaces providing a cosy atmosphere, and deck or patio areas superb for enjoying the outdoors. Many properties also feature blenders and coffee/tea makers, suiting those who appreciate a morning brew or want to whip up smoothies.
When is the best time to visit Westport for a holiday rental?
The peak season for holiday rentals in Westport typically spans from May to July, with July being the most popular month for visitors. This vibrant period draws families and beachgoers alike, eager to enjoy the sun-soaked beaches and the charming coastal atmosphere. The warm temperatures, often reaching the mid to high 20s Celsius, create great conditions for outdoor activities, from sunbathing to kayaking in the Long Island Sound.

During these months, Westport comes alive with various events, farmers' markets, and cultural activities, making it an ideal time for those seeking a lively holiday experience filled with local flavour. You'll also find that the town's picturesque parks and scenic waterfront are great for leisurely strolls or picnics.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience, allowing you to appreciate the stunning autumn foliage and the serenity of Westport's natural beauty without the summer crowds. The crisp air can be refreshing, great for scenic walks along the coast or exploring the local shops and eateries.
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 blend of natural beauty and cultural attractions. The town's beautiful beaches, such as Compo Beach, offer stunning views of the Long Island Sound and are superb for sunbathing and picnicking. Nearby, the Westport Country Playhouse presents a range of theatrical performances, making it a cultural highlight in the area.

For those interested in art, the Westport Arts Centre features exhibitions and events that showcase local talent. Additionally, the picturesque Saugatuck River runs through the town, providing opportunities for kayaking and scenic walks along the riverfront.
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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