Westport holiday rentals

We found 499 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

Living room
View of back of house
Front of house
Stairs leading to third floor
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
AU$12,277
for 7 nights, 1 home
AU$1,754 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Room
Living area
Pool
Terrace/patio
Exceptional
(5 reviews)

2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC

Fairfield

8% off
AU$30,030
for 7 nights, 1 home
AU$4,290 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Dining
Terrace/patio
Property grounds
Pool
Exceptional
(5 reviews)

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Trumbull

8% off
AU$14,350
for 7 nights, 1 home
AU$2,050 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Living area
Marina
Interior
Exterior
Wonderful
(16 reviews)

<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽

Stamford

7% off
AU$1,965
for 7 nights, 1 apartment
AU$281 per night
includes taxes & fees
<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽
Living area
Living area
Room
Private kitchen
Very good
(13 reviews)

❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC

Stamford

7% off
AU$2,001
for 7 nights, 1 apartment
AU$286 per night
includes taxes & fees
❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC
Room
Interior
Interior
Interior
Exceptional
(10 reviews)

The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

Stamford

5% off
AU$1,422
for 7 nights, 1 apartment
AU$203 per night
includes taxes & fees
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Del Vino Vineyards (15.9 mi / 25.6 km)
  • Country Club of Fairfield (4.5 mi / 7.2 km)
  • Connecticut Golf Club (8.6 mi / 13.9 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)
  • 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)
  • Seaside Beach (8.2 mi / 13.2 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Westport holiday homes prices shown on Stayz?
Stayz 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.
Are there any Westport holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Westport holiday homes?
You can find great discounts on holiday homes in Westport on Stayz, 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.
Can I change or cancel my Westport holiday home booking on Stayz?
To find Westport holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Westport?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Westport holiday home?
Book your Westport holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Westport?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Westport to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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