Madison vacation rentals

We found 426 vacation rentals — enter your dates for availability

Select from 32 homes, 11 cottages, and other vacation rentals in Madison to find one that's perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the amenities you need and want, such as WiFi and cable TV. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Madison

Why visit Madison

  • Beautiful beaches: Madison boasts stunning coastline views, ideal for relaxation and sunset watching.
  • Charming downtown: Explore local shops and eateries in a family-friendly atmosphere.
  • Historic attractions: Discover the rich history through various historic houses and landmarks.
  • Outdoor activities: Enjoy hiking, biking, and exploring nearby state parks for adventure seekers.
  • Variety of accommodations: Choose from private vacation homes, cozy cottages, and comfortable apartments for a memorable stay.

Popular types of accommodation in Madison

If you’re planning a getaway to Madison, the next exciting step is selecting your perfect accommodation. Our platform offers a variety of options, including houses, charming cottages, and cozy apartments. With a focus on transparency and savings, you’ll find the ideal home rental to fit your needs. Explore the best Madison vacation rentals and discover the amenities that make your stay unforgettable.

  • Houses: The top choice for visitors to Madison, these homes offer spacious accommodations ideal for families and groups, providing a home-like atmosphere.
  • Cottages: A charming option for a cozy getaway, cottages in Madison are perfect for those seeking a quaint and relaxing stay.
  • Apartments: A convenient choice, apartments offer the comforts of home with easy access to local attractions.
  • Cabins: For nature enthusiasts, cabins provide a rustic escape surrounded by natural beauty.
  • Condos: A great alternative for travelers seeking modern amenities and community facilities in a vibrant setting.**

Top attractions in and around Madison

Madison, Connecticut, is a perfect destination for outdoor enthusiasts and adventure seekers. With its stunning scenery, you can explore local attractions like beautiful beaches, historic houses, and nearby state parks. Whether you’re looking for cultural experiences or thrilling outdoor activities, Madison offers a variety of points of interest that cater to all types of travelers, making it an ideal spot for a memorable vacation.

  • Hammonasset Beach State Park: This expansive national park offers stunning scenery and adventure with its beautiful trails, picnic areas, and outdoor activities, perfect for nature lovers and families alike.
  • Hammonasset Beach: Known for its picturesque beach vibes, this popular destination provides a perfect spot for swimming, sunbathing, and beachcombing along a long stretch of sandy shoreline.
  • Chaffinch Island State Park: Located 6 miles away, this tranquil state park is budget-friendly and features relaxing vibes, making it an ideal escape for a peaceful day surrounded by nature.

Things to do recommended for couples

Madison, Connecticut, offers a charming experience for couples. Enjoy a scenic walk along the beach at Hammonasset State Park, explore the quaint shops downtown, or savor a romantic dinner at a cozy waterfront restaurant. Don't miss a sunset stroll along the picturesque shoreline for unforgettable memories.

Things to do recommended for families

Your family will love exploring the scenic beaches of Hammonasset State Park, where kids can build sandcastles and enjoy picnics. The nearby Madison Historical Society offers engaging exhibits that bring local history to life, making it a fun and educational stop for all ages.

Things to do recommended for groups

Groups visiting Madison can enjoy a scenic day at Hammonasset Beach State Park, explore the charming downtown with its unique shops and eateries, and take a guided tour of the historic Madison Lighthouse for stunning coastal views.

*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 Madison

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—it's important to prioritize your preferences during your search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Madison with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Madison with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Madison: For many families, a vacation wouldn't be the same without their beloved pets. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Madison: If you're searching for vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can quickly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Madison

Madison, Connecticut, offers a delightful blend of outdoor adventures and scenic beauty. Visitors can explore the charming downtown area, where family-friendly vibes meet local shops and eateries. Just a short drive away, you can experience the vibrant atmosphere of nearby New York City. Don't miss the stunning sunsets along the coastline, perfect for relaxation and unwinding after a day of exploration. Madison is truly a gem for travelers seeking both luxury and recreation.

  • Westbrook: Located a mere 7 miles from Madison, Westbrook is a charming coastal town that offers a delightful blend of outdoor adventures and romantic scenery. Visitors can enjoy a variety of activities, including relaxing at the local beaches or indulging in a round of golf at one of the nearby courses. Westbrook is also known for its vibrant music concerts and upscale resorts, making it a great destination for those seeking both relaxation and entertainment. The picturesque views along the shoreline and the family-friendly beaches make it a perfect spot for visitors of all ages.
  • Old Saybrook: Situated 10 miles from Madison, Old Saybrook is a quaint town steeped in history and natural beauty. This area is perfect for outdoor enthusiasts, boasting scenic parks and stunning beaches. Visitors can explore the recreational areas or unwind at luxurious resorts after a day of adventure. Old Saybrook is also home to a national state park, providing ample opportunities for hiking and wildlife watching. The romantic charm of this town, combined with its beautiful landscapes, makes it an ideal getaway for couples and families alike.
  • Clinton: Just 2 miles from Madison, Clinton is a lively town known for its outdoor adventures and scenic views. The area offers a plethora of recreational activities, including golf courses and shopping at local centers. Visitors can take advantage of the nearby beaches and the national state park, perfect for hiking and exploring nature. Clinton's blend of adventure and relaxation makes it a fantastic choice for those looking to immerse themselves in the beauty of Connecticut's shoreline.

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 hoping to save on your next getaway? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for an extended stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to refine your search by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Vrbo Trips: Planning made easy

Vrbo’s cutting-edge Trip Board offers you a convenient place to plan new trips, pick up right where you left off, or manage your travel arrangements. You can easily access the properties you’ve saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Discover New England's marvelous Madison

Nestled against the shoreline of Connecticut's Long Island Sound, and just a 30-minute drive from New Haven, Madison offers a postcard-perfect example of New England picturesque. From days spent shopping at the independent stores and eateries in the town's charming downtown to relaxing along the unspoiled coastline at Hammonasset Beach State Park, ample activities and attractions allow travelers to explore at their own pace. If you're planning to stay a while, Madison vacation rentals are the perfect way to stay close to the action, offering a relaxed base for your getaway, whether traveling with family, friends or both.

Activities and attractions in Madison

Do you want to find things to do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Madison a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Chamard Vineyards (1.7 mi / 2.8 km)
  • Essex Steam Train (9.6 mi / 15.5 km)
  • Stay and Play LLC (9.8 mi / 15.8 km)
  • Connecticut Sportsplex (12.7 mi / 20.5 km)
  • Machimoodus State Park (14.7 mi / 23.7 km)
  • Powder Ridge Mountain Park and Resort (16.6 mi / 26.7 km)

Find your perfect spot in Madison

Indoors or outside, Madison offers a quintessential New England experience. The town's quaint downtown features independent dining spots and boutique stores selling handcrafted bird boxes, not to mention an old-fashioned movie theater and a world-famous bookseller. Travelers keen to soak up more of the same can explore nearby New Haven, while those who prefer natural surroundings can find their perfect spot on the sand along the 2 miles of beachfront at Hammonasset Beach State Park. Over the summer, free events such as S'mores on the Shore movie nights and Wednesday-night concerts are a lovely way to end the day.

Seasonal appeal in Madison

Madison weather is fairly typical of New England. Daytime temperatures over the summer months of July and August can soar toward 90 degrees, although breezes floating in from Long Island Sound can prevent the stuffy air of further inland. Despite the appeal of spending sun-drenched summers in Madison vacation rentals, there's little debate that the best time to visit anywhere in New England is during fall. Brilliant colors start to turn the foliage into a dazzling display of red, orange and yellow - and the daytime temperatures are still plenty warm enough to get outside and enjoy the show.

Natural wonders near Madison

The appeal of the unspoiled sandy beach at Hammonasset Beach State Park can't be understated but travelers willing to travel a little further afield will find numerous natural delights on the menu. The East River Wildlife Area, located at the edge of Madison's western border is home to all manner of creatures, including American oystercatchers and majestic great blue herons, making it the perfect spot for wildlife watching and photography. To the northeast of the town, the 16,000-acre Cockaponset State Forest offers hiking, horseback riding and mountain biking for much of the year, and cross-country skiing and snowmobiling in winter.

Transportation to and around Madison

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 16.5 mi (26.5 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to New London, CT (GON-Groton - New London), which is 27.6 mi (44.4 km) away.

Frequently asked questions

What is the best area to stay in Madison, Connecticut, United States of America when booking a vacation rental?
When looking for the best area to stay in Madison, Connecticut, you'll want to consider the charming downtown area, which offers a delightful blend of local shops, cafes, and restaurants. This vibrant neighborhood is not only convenient for accessing various amenities but also brings a sense of community and warmth. Visitors can enjoy the scenic views along the shoreline, with nearby beaches like Hammonasset Beach State Park providing ample opportunities for outdoor activities and relaxation.

Another great option is the picturesque neighborhood around Madison's historic district. This area is known for its beautiful architecture and rich history, making it a lovely place to explore on foot. You can visit the iconic Madison Historical Society Museum for a glimpse into the town's past and enjoy the serene atmosphere of the nearby green spaces.

In terms of vacation rentals, Madison features a variety of properties, from cozy cottages to spacious homes, allowing for a comfortable stay regardless of your travel needs.
How much does it cost to rent a vacation home in Madison?
Prices for vacation 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 vacation 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, travelers should consider the picturesque shoreline along the Long Island Sound. The area around Hammonasset Beach State Park is particularly popular, offering easy access to sandy beaches and scenic views. Many beach houses in this vicinity come equipped with essential amenities such as outdoor decks, private patios, and barbecue grills, superb for enjoying the coastal atmosphere. Additionally, some properties may feature direct beach access, making it convenient for families or groups to spend their days by the water.

Further north, the neighborhoods near East Wharf Beach provide charming options with a more laid-back vibe. Here, travelers can find rentals that often include modern kitchens, spacious living areas, and outdoor showers, making it easy to rinse off after a day at the beach. This area is also close to local restaurants and shops, enhancing the convenience for vacationers.

In Madison, the scenic views can be complemented by nearby attractions such as the Madison Historical Society and various parks, which offer opportunities for hiking and exploring the natural beauty of the region. Find your rental near the beach in Madison.
Where are the best Madison ski resort rentals?
For skiing near Madison, Connecticut, the closest ski resorts are located in the nearby regions, with the most popular being in the Berkshires of Massachusetts or around the greater New Haven area. One of the best options is to look towards the town of Lakeville, which is about an hour's drive from Madison. Here, travelers can find rentals that provide easy access to nearby ski areas like Catamount Ski Area, which offers a variety of trails suitable for different skill levels.

In Lakeville, you can expect a range of cozy cabins and vacation homes equipped with amenities such as fireplaces, modern kitchens, and outdoor spaces for enjoying the winter scenery. Many properties may also feature hot tubs or saunas, great for relaxing after a day on the slopes. The picturesque setting of Lakeville, with its beautiful lakes and rolling hills, adds to the appeal, providing a serene backdrop for a winter getaway.

Additionally, the nearby town of Goshen offers more rental options, often in quaint rural settings. These properties typically come with rustic charm, comfortable living areas, and proximity to local shops and dining. Travelers can also explore the scenic landscapes, with opportunities for snowshoeing and cross-country skiing in the surrounding areas.
What is the most popular type of vacation rental accomodation in Madison?
In Madison, vacation houses are the most popular rental choice, with about 25 available throughout the area. These houses often feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups. Many properties also include outdoor spaces such as decks or patios, allowing guests to enjoy the pleasant coastal climate. Additionally, there are several cottages and apartments available that provide a charming and cozy atmosphere, superb for a relaxing getaway.
Are there any family house rentals in Madison?
In Madison, Connecticut, there are around 26 family-friendly house rentals available, making it an excellent choice for those traveling with kids. This charming coastal town features neighborhoods close to beautiful beaches and parks, superb for family outings. Many of these homes offer spacious living areas, fully equipped kitchens for family meals, and outdoor spaces where children can play and adults can relax.

Visitors can explore local attractions like the Madison Town Green, which often hosts community events and has playgrounds for younger visitors. Additionally, the nearby Hammonasset Beach State Park provides opportunities for swimming, picnicking, and hiking along scenic trails.
Can I rent a vacation home with a pool or hot tub in Madison?
In Madison, Connecticut, travelers looking for vacation homes with pools or hot tubs will find several options available. This charming coastal town offers a beautiful setting for relaxation, with many properties located near the shoreline and within residential neighborhoods. Expect to find amenities such as private swimming pools, hot tubs, and spacious outdoor areas superb for family gatherings or quiet retreats. Many rentals also feature fully equipped kitchens and comfortable living spaces, making them ideal for both leisure and entertainment.
Can I find long-stay vacation rentals in Madison?
A long-stay vacation rental in Madison is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Madison?
In Madison, there are several pet-friendly house rentals available, with around 13 options to choose from. Many of these vacation homes come equipped with modern amenities such as full kitchens, spacious living areas, and outdoor spaces for relaxation. Some properties may include features like fenced yards, which are ideal for pets to roam freely.

The area itself is known for its beautiful coastal scenery and proximity to parks. A highlight is the nearby Hammonasset Beach State Park, which offers walking trails and sandy shores where pets are welcome on leashes, making it a great spot for outings with your furry companions. See all pet-friendly rentals in Madison.
Are there any remote work vacation rentals in Madison?
In Madison, Connecticut, there are numerous vacation rentals that cater to remote workers, with about 35 options available in the area. Many of these properties are well-equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces including desks and chairs, and often additional features like printers for those needing to manage tasks while away from home.

Travelers can expect a variety of accommodations, ranging from cozy cottages to spacious homes, typically situated near local points of interest such as the beautiful beaches along the Long Island Sound, charming downtown shops, and parks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Madison vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Madison with parking available—perfect for families or travelers 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 vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals during their stay. Many rentals also feature outdoor spaces such as decks or patios, superb for enjoying the pleasant Connecticut weather. Additional amenities often found in these properties include blenders for making smoothies or cocktails, onsite parking for convenience, and porches or lanais that provide a charming spot to relax and take in the local scenery.
When is the best time to visit Madison for a vacation rental?
July is the most popular time to visit Madison, Connecticut, when the warm summer months from June to August draw in vacationers eager to enjoy the coastal charm and vibrant local culture. This peak season offers ideal conditions for outdoor activities, such as beach days at Hammonasset Beach State Park, where families can relax in the sun or indulge in water sports along the beautiful shoreline.

During July, guests can expect pleasant weather, typically ranging from the mid-60s to mid-80s Fahrenheit, superb for sightseeing or exploring the picturesque downtown area filled with boutiques, restaurants, and art galleries. The lively option is enhanced by local events and festivals, creating a memorable experience for those looking to immerse themselves in Madison's community spirit.

For travelers seeking a more budget-friendly option, consider visiting in December. While this month is quieter, it provides a unique opportunity to experience Madison's charming winter landscape. Enjoy picturesque walks through the town adorned with holiday decorations and cozy cafes superb for warming up after a stroll.

Ultimately, the best time to book a vacation rental in Madison hinges on your preferences for vibrant summer activities or the peaceful ambiance of the winter season.
How early should I book a Madison vacation rental?
Book your Madison vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Madison, Connecticut, United States of America?
In Madison, Connecticut, visitors can explore a variety of attractions that highlight the town's coastal charm and natural beauty. The picturesque Madison Town Green is a central hub, often hosting community events and featuring historic buildings. Nearby, the scenic beaches, such as Hammonasset Beach State Park, offer sandy shores, picnic areas, and walking trails along the coast, making it a great spot for outdoor activities and relaxation.

Visitors can also enjoy the historic charm of the downtown area, where quaint shops, cafes, and restaurants provide a delightful local experience. For nature enthusiasts, the Madison Land Conservation Trust offers numerous trails for hiking and birdwatching, showcasing the region's diverse flora and fauna.
Can I change or cancel my Madison home rental booking on Vrbo?
To find Madison vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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