Madison holiday lettings

We found 438 holiday rentals — enter your dates for availability

Select from 33 homes, 10 cottages and other holiday rentals in Madison to find one that's perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a washer and dryer. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Madison

Showing deals for:4 Sept - 11 Sept

Image gallery for Cozy East Haven Home • Near Beach & Yale

Exterior detail
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Cozy East Haven Home • Near Beach & Yale

East Haven

8% off
Price is £1,508
for 7 nights, 1 home
£215 per night
includes taxes & fees
Cozy East Haven Home • Near Beach & Yale

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Why visit Madison

  • Outdoor Adventures: Madison offers a plethora of outdoor activities, including national parks and picturesque beaches, perfect for nature lovers.
  • Charming Downtown: Explore the vibrant Madison Centre with friendly locals and a welcoming atmosphere, ideal for leisurely strolls.
  • Family-Friendly Vibe: The coastal regions provide a delightful setting for family outings and scenic enjoyment.
  • Relaxing Cinemas: Unwind in the evenings at local cinemas after a day of exploration.
  • Diverse Accommodation: Choose from private vacation homes, charming cottages, and stylish apartments to suit your preferences and budget.

Popular types of accommodation in Madison

If you're considering a getaway to Madison, you're in for a treat! Our most sought-after accommodation options include Houses, charming Cottages, and stylish Apartments. Whether you're looking for apartment rentals, house rentals, or cosy home rentals, we provide a wide array of rental listings in Madison to ensure you find the perfect stay. Enjoy your holiday with transparency, savings, and peace of mind.

  • Houses: The top choice for visitors in Madison, offering spacious and comfortable settings for families or groups.
  • Cottages: A charming option, these quaint retreats provide a homely atmosphere near the picturesque coastline.
  • Apartments: Ideal for solo travellers or couples, these provide a convenient and stylish base for exploring Madison.
  • Cabins: A rustic escape, perfect for those seeking a tranquil retreat surrounded by nature.
  • Condos: A modern alternative, these offer amenities and are often located in vibrant areas for easy access to local attractions.**

Top attractions in and around Madison

Madison, Connecticut, is an excellent destination for outdoor enthusiasts and adventure seekers, boasting a range of attractions such as national parks, picturesque beaches, and a railway museum. Visitors can immerse themselves in the local culture while enjoying various outdoor activities. Additionally, Madison's cinemas provide a delightful option for a relaxing evening after a day of exploration.

  • Hammonasset Beach State Park: This expansive park offers a delightful blend of outdoor adventure and stunning scenery. Enjoy hiking, picnicking, and birdwatching, or simply relax amidst the natural beauty of the Connecticut shoreline.
  • Hammonasset Beach: A lovely stretch of sandy shore, perfect for sunbathing, swimming, and beachcombing. The tranquil waters and picturesque views create a relaxing seaside atmosphere.
  • Essex Steam Train: Just 6.2km away, this charming railway museum provides a nostalgic journey through history with scenic rides aboard vintage steam locomotives, immersing you in the region's rich culture.

Things to do recommended for couples

For a romantic getaway in Madison, visit Chamard Vineyards for delightful wine tasting, indulge in a meal at Anna Mia's for a cosy atmosphere, or embrace adventure at Powder Ridge Mountain Park for skiing. Each spot offers a unique charm perfect for couples.

Things to do recommended for families

During your family vacation in Madison, Connecticut, enjoy thrilling activities such as the Connecticut Sportsplex for sports enthusiasts, Stay and Play LLC for arcade adventures, and the charming Greenport Carousel for a delightful outdoor experience with the family.

Things to do recommended for groups

Explore the Clinton Crossing Premium Outlets for a delightful shopping experience, just 1.2km from Madison. Visit RJ Julia Booksellers for a literary adventure, or head to the North Madison Shopping Centre, where you can enjoy a vibrant atmosphere filled with family-friendly options.

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

When travelling with a group, family, pets, or if you're seeking longer stays, it's essential to filter according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Madison with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Madison with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities, such as a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Madison: For many families, a trip wouldn’t feel complete without their beloved four-legged companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Madison: If you’re in search of holiday rentals offering discounts 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 features such as a parking space, a lovely kitchen, or even a private pool in your search criteria.

Where to stay near Madison

Madison, Connecticut, offers a delightful blend of outdoor adventures and scenic beauty, ideal for a memorable getaway. Explore the charming Madison Centre and the vibrant downtown area, where you'll find friendly locals and a welcoming atmosphere. Nearby, enjoy the family-friendly vibe of the coastal regions and picturesque landscapes. Whether you're seeking luxury or a relaxing budget break, Madison promises a unique experience that caters to all tastes and preferences.

  • Westbrook: Situated approximately 4.3km from Madison, Westbrook is a charming coastal town known for its stunning outdoor experiences and romantic scenery. Visitors are drawn to its beautiful beaches, making it an ideal spot for a relaxing day by the sea. The local resorts offer a perfect getaway, while music concerts provide entertainment throughout the year. Don't miss the recreational areas where you can engage in various outdoor activities. Whether it's sunbathing on the family beach or attending an event at the conference venue, Westbrook promises a delightful escape.
  • Old Saybrook: Located around 6.2km from Madison, Old Saybrook enchants visitors with its picturesque landscapes and outdoor adventures. This quaint town is famous for its scenic beaches and tranquil lake, offering plenty of opportunities for a romantic stroll or a peaceful day by the water. Golf enthusiasts can enjoy the local courses, while music concerts in the area provide a lively atmosphere. With its charming waterfront and recreational areas, Old Saybrook is a perfect destination for those seeking both relaxation and adventure.
  • Clinton: Just 1.2km from Madison, Clinton is a vibrant town that beckons adventurers and nature lovers alike. Known for its stunning beaches and access to a national state park, Clinton offers countless outdoor activities, from hiking to swimming. Visitors can indulge in the lively music scene, enjoy delightful resort stays, and explore the recreational areas that define this coastal gem. With its proximity to Madison, Clinton is an ideal spot for a quick escape into nature and excitement.

Best time to go to Madison

If you're planning a trip to Madison, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnyAverageModerately Low
February32.4°F (0.2°C)Light RainMostly SunnyAverageModerately Low
March38.5°F (3.6°C)Light RainMostly SunnyAverageModerately Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June66.4°F (19.1°C)Light RainMostly SunnyModerately HighModerately High
July73.8°F (23.2°C)Light RainMostly SunnyModerately HighModerately High
August72.7°F (22.6°C)Light RainMostly SunnyModerately HighModerately High
September66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
October56.5°F (13.6°C)Light RainMostly SunnyModerately LowAverage
November45.5°F (7.5°C)Light RainMostly SunnyModerately LowAverage
December37.8°F (3.2°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming holiday? It might be worth considering some flexibility with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant 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 made easy

Vrbo's Trip Board offers a handy platform for you to plan new adventures, resume previous arrangements, or manage your travel itineraries. You can easily find the properties you’ve saved or booked, neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Head to the luxury city of Madison

The beaches and other outdoor surroundings create an inviting atmosphere in Madison. Renowned for its fishing, aquarium and cheese shops, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Madison

Do you want to find attractions to visit in the city? Venture out of your holiday home and experience everything that makes Madison a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Chamard Vineyards (1.6 mi / 2.6 km)
  • Chatfield Hollow State Park (4.9 mi / 8 km)
  • Machimoodus State Park (14.7 mi / 23.7 km)
  • Powder Ridge Mountain Park and Resort (16.6 mi / 26.7 km)
  • Kontokosta Winery (16.6 mi / 26.7 km)
  • 8 Hands Farm (18.9 mi / 30.4 km)

Exploring the natural features in Madison

Whether you're an active traveller or just want to appreciate the scenery, Madison is a great place to spend some time outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Clinton Town Beach (3.5 mi / 5.6 km)
  • Hammonasset Beach (3.5 mi / 5.7 km)
  • Chatfield Hollow State Park (4.9 mi / 8 km)
  • Westbrook Town Beach (6.3 mi / 10.2 km)
  • Harvey's Beach (9.5 mi / 15.3 km)
  • Goose Island (12 mi / 19.4 km)

Seasonal weather averages in Madison

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 21°C.

Transport to and around Madison

Fly into New Haven, CT (HVN-Tweed - New Haven Regional), the closest airport, located 16.5 mi (26.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into New London, CT (GON-Groton - New London), which is 27.6 mi (44.4 km) away.

If you'd rather travel by train, the main station is Madison Station.

Frequently asked questions

What is the best area to stay in Madison when booking a holiday rental?
When considering a holiday rental in Madison, Connecticut, a popular area to stay in is the charming downtown district. This area offers a delightful selection of properties that range from quaint cottages to more modern homes, providing a variety of options for visitors. Staying in downtown Madison allows easy access to its lovely shops, cafés, and restaurants, making it a vibrant spot for enjoying local flavours.

Another great option is the beachfront neighbourhood along the Long Island Sound. This area boasts stunning views and a relaxed atmosphere, superb for those looking to unwind by the water. Properties here often feature outdoor spaces where guests can soak up the natural beauty of the coastline. A highlight of this location is the picturesque Hammonasset Beach State Park, which offers beautiful sandy shores and scenic trails for walking and biking.

Additionally, both areas are close to attractions such as the Madison Historical Society and the charming Scranton Memorial Library, which adds to the cultural experience of your stay.
How much does it cost to rent a holiday home in Madison?
Prices for holiday rentals in Madison 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 Madison 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 Madison holiday house rentals?
You can find great discounts on house rentals in Madison 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 Madison?
For renting a beach house in Madison, the picturesque shoreline along the Long Island Sound is an ideal choice. The area around East Wharf Beach offers lovely rental options with stunning views and easy access to the sandy beach. Many properties here come equipped with amenities such as spacious decks, outdoor grills, and fully stocked kitchens, superb for family gatherings or socialising with friends after a day by the water.

Just a short stroll away, the charming town centre of Madison provides a delightful mix of local shops and eateries, enhancing the coastal experience. For those seeking a bit more privacy, the neighbourhoods around Hammonasset State Park present further opportunities, where you can find beach houses that often feature private yards, fire pits, and direct beach access—ideal for beachcombing or enjoying evening bonfires.

Additionally, the scenic views and tranquil atmosphere of the nearby Madison Surf Club area make it a popular spot for beach rentals. Here, many properties boast amenities like outdoor showers and spacious living areas, allowing guests to relax comfortably after a long day at the beach.
What is the most popular type of holiday rental accomodation in Madison?
In Madison, holiday houses are the most popular type of holiday rental, with around 75 available throughout the town. These homes typically offer spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens, making them ideal for families or groups. Additionally, there are about 27 cottages scattered across charming neighbourhoods, providing a quaint and cozy atmosphere for guests looking to enjoy a more intimate setting. While there are several apartments available, they are less common compared to the abundance of houses and cottages.
Are there any family house rentals in Madison?
In Madison, Connecticut, there are some available family-friendly house rentals, with around 26 options to choose from. This charming coastal town offers a delightful mix of beach access and small-town charm, making it superb for families. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to play. Additionally, amenities like Wi-Fi and air conditioning ensure a comfortable stay.

The locale is close to scenic spots such as Hammonasset Beach State Park, which boasts beautiful sandy shores and picnic areas, ideal for family outings. Visitors can also explore local attractions like the Madison Historical Society or the quaint shops and eateries in the town centre.
Can I rent a holiday home with a pool or hot tub in Madison?
In Madison, Connecticut, there are several holiday homes available for rent that feature pools or hot tubs, providing a great option for those seeking relaxation and leisure during their stay. The charming coastal town offers a range of properties, especially in neighbourhoods close to the picturesque shoreline and local parks. Many of these rentals include private pools, outdoor patios, and hot tubs, making them ideal for families or groups looking to unwind after a day of exploring the area. Additional amenities often include fully equipped kitchens, spacious living areas, and outdoor grilling facilities, ensuring a comfortable and enjoyable experience.
Can I find long-stay holiday rentals in Madison?
A long-stay holiday rental in Madison 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 Madison?
In Madison, there are several pet-friendly house rentals available, offering a range of amenities to ensure a comfortable stay for both travellers and their furry companions. Many of these properties feature spacious yards, allowing pets to roam freely, as well as outdoor areas where guests can relax and enjoy the surroundings.

The town is known for its beautiful coastal scenery, and many rentals provide easy access to nearby parks and beaches where pets are welcome. For instance, the scenic Hammonasset Beach State Park is a fantastic spot for outdoor adventures with your pet, boasting walking trails and sandy shores. Additionally, the charming downtown area of Madison offers pet-friendly cafes and shops, enhancing the overall experience for those travelling with pets.
Are there any remote work holiday rentals in Madison?
In Madison, Connecticut, there are numerous remote work-friendly holiday rentals available, with around 105 options to choose from. This charming coastal town offers a blend of natural beauty and small-town charm, making it an appealing destination for those looking to work remotely. Many of these properties are equipped with essential amenities such as high-speed Wi-Fi, dedicated desks, and comfortable desk chairs, ensuring a productive environment for remote workers.

The area is known for its picturesque beaches, including the scenic Hammonasset Beach State Park, where you can unwind after a day of work. Additionally, the town features delightful local shops and restaurants, providing convenient options for dining and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Madison holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Madison 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 Madison?
In Madison, popular holiday rental amenities include well-equipped kitchens that allow guests to prepare their own meals, along with decks or patios for enjoying the outdoors. Many rentals also feature blenders, making it easy to whip up smoothies or other beverages. Onsite parking is commonly available, providing convenience for those travelling with vehicles. Additionally, many properties offer porches or lanais, which create a pleasant space for relaxation while taking in the local scenery.
When is the best time to visit Madison for a holiday rental?
The peak season for visiting Madison, Connecticut, is during the summer months of June through August, with July being especially popular among holidaymakers. This vibrant period attracts visitors eager to enjoy the coastal charm of this picturesque town, with its lovely beaches, waterfront dining, and numerous outdoor activities. The warm weather, typically ranging from 23 to 30 degrees Celsius, creates a friendly space for sunbathing, swimming, and exploring the local parks.

While July is bustling with tourists, the comfortable climate makes it ideal for a variety of activities, from leisurely strolls along the shore to adventurous kayaking on the Long Island Sound. The lively summer events, including local festivals and farmers' markets, add to the town's appeal, ensuring there's always something enjoyable happening nearby.

For those looking for a more budget-friendly experience, consider visiting in December. This quieter month provides a charming winter atmosphere, great for cosy getaways, holiday shopping, and enjoying the festive decorations throughout the town. You can also take part in seasonal events, such as tree lighting ceremonies and winter markets, which offer a unique perspective on Madison's community spirit.
How early should I book a Madison holiday rental?
Book your Madison 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 Madison?
In Madison, Connecticut, visitors can enjoy a range of attractions that highlight the town's coastal charm and rich history. The picturesque shoreline along Long Island Sound offers beautiful beaches such as Hammonasset Beach State Park, which is superb for swimming, picnicking, and hiking along the scenic trails.

The historic downtown area features quaint shops, restaurants, and the iconic Madison Green, where community events often take place. The nearby Scranton Memorial Library is not only an architectural gem but also provides a peaceful spot for reading and reflection.

For those interested in outdoor activities, the town has various parks and nature reserves, including the picturesque Hammonasset State Park, which is great for birdwatching and offers miles of walking trails. The local arts scene can be appreciated at the Madison Art Cinema, providing a mix of independent and mainstream films.
Can I change or cancel my Madison home rental booking on Vrbo?
To find Madison 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 Madison 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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