Madison vacation rentals

We found 427 vacation rentals — enter your dates for availability

Select from 33 homes, 10 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.

Vacation rentals with weekly discounts - Madison

Showing deals for:Nov 7 - Nov 14
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Find out more about Madison

Find out more about Madison

Why visit Madison

  1. Scenic State Parks: Madison is home to stunning state parks offering outdoor adventures, hiking trails, and breathtaking views.
  2. Charming Beaches: Relax on picturesque beaches along the coastline, perfect for sunbathing or picnicking.
  3. Local Railway Museum: Discover the town's history and charm at the railway museum, showcasing fascinating exhibits.
  4. Vibrant Downtown: Explore the lively downtown area filled with friendly locals, shops, and art-filled streets.
  5. Diverse Accommodation: Enjoy a range of vacation rentals, from cozy cottages to convenient apartments, catering to all budgets.

Popular types of accommodation in Madison

If you're looking to explore Madison, you're in the right place! Our platform offers a variety of popular vacation rentals, including houses, charming cottages, and convenient apartments. Whether you need a cozy spot for relaxation or an ideal apartment with meeting room facilities, you’ll find the perfect fit for your stay in Madison. Enjoy transparency and savings while discovering the best vacation rentals in this vibrant city!

  • Houses: The top choice among visitors to Madison, these spacious homes are ideal for families or groups seeking comfort and privacy.
  • Cottages: A delightful option for those looking for a quaint and picturesque stay, perfect for a romantic getaway or a serene retreat.
  • Apartments: These convenient lodgings offer a home-like atmosphere, often in prime locations for easy access to local attractions.
  • Cabins: For nature enthusiasts, these rustic getaways provide a tranquil escape amidst beautiful surroundings.
  • Condos: A popular choice for visitors seeking modern amenities and shared facilities while enjoying a vacation experience.**

Top attractions in Madison

Madison, Connecticut, is an ideal destination for outdoor enthusiasts and adventure seekers. Visitors can explore stunning state parks, relax on picturesque beaches, and discover the charm of the local railway museum. This lovely town offers a variety of attractions that cater to those looking for cultural experiences and scenic adventures, making it a perfect getaway for families, groups, or solo travellers.

  1. Hammonasset Beach State Park: This stunning state park offers a unique blend of adventure and serene scenery, perfect for outdoor enthusiasts. Enjoy hiking trails, picnicking, and breathtaking views of the Long Island Sound.
  2. Hammonasset Beach: A beautiful stretch of sandy shoreline, ideal for sunbathing and swimming. The beach vibes are relaxing, making it a perfect spot to unwind by the water.
  3. Meigs Point Nature Center: An eco-friendly centre that promotes environmental awareness. Explore interactive exhibits and learn about local ecosystems while enjoying the natural beauty of the area.

Things to do recommended for couples

Ready for a romantic getaway in Madison? Visit Chamard Vineyards for a delightful wine tasting, enjoy a lovely dinner at Anna Mia's, or embrace the thrill of winter sports at Powder Ridge Mountain Park. Each experience offers a unique charm perfect for couples looking to connect.

Things to do recommended for families

Experience family fun at Connecticut Sportsplex, a vibrant sports facility 20.9km from Madison. Enjoy arcade adventures at Stay and Play LLC, located 16.1km away. For relaxation, visit Devil’s Hopyard State Park, also 20.9km distant, offering a serene natural setting.

Things to do recommended for groups

Explore the Clinton Crossing Premium Outlets for a fantastic shopping experience, only 3.2km from Madison. Visit RJ Julia Booksellers for a cozy bookshop atmosphere, and don’t miss the North Madison Shopping Center for family-friendly shopping and city vibes.

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

If you're travelling with friends, family, pets, or planning an extended stay, it's important to refine your search according to your specific needs. 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 space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Madison with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance the experience.
  • Taking your pets with you to Madison: For many families, a trip isn't truly fulfilling without their furry companions. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with 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 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 effortlessly 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 as well.

Where to stay in Madison

Madison, Connecticut, offers a charming blend of outdoor adventures and picturesque scenery, ideal for a memorable vacation. Explore the vibrant downtown, where friendly locals and art-filled streets create a welcoming atmosphere. Discover the stunning waterfront views and the serene Edmonds area, perfect for relaxation. Nearby neighborhoods provide a family-friendly vibe, ensuring a delightful experience for all travellers. Whether you seek luxury or budget-friendly options, Madison has something for everyone.

  • Old Saybrook: Located approximately 16.1km from Madison, Old Saybrook is a charming coastal city known for its stunning outdoor scenery and romantic atmosphere. Visitors can enjoy a variety of activities such as golfing and exploring local recreational areas. The city is famous for its beautiful beaches and lakes, making it an ideal spot for families and nature lovers. Don't miss the chance to unwind at the scenic waterfront or visit local casinos for some entertainment.
  • Westbrook: Just 11.3km away from Madison, Westbrook is a delightful city that offers a perfect blend of outdoor adventures and romantic experiences. Known for its beautiful beaches and vibrant local culture, Westbrook is an excellent destination for those seeking relaxation and fun. Visitors can enjoy music concerts, stay at luxurious resorts, or try their luck at local casinos. The town's event conference venues also attract various gatherings, making it a lively spot year-round.
  • Clinton: Only 3.2km from Madison, Clinton is a vibrant city that beckons adventure seekers and nature enthusiasts alike. With its stunning beaches and access to a national state park, visitors can indulge in outdoor activities amidst breathtaking scenery. Popular attractions include recreational areas and music concerts, providing a lively atmosphere for all ages. Clinton's proximity to Madison makes it an easy and enjoyable day trip, perfect for those looking to explore the best of Connecticut's coastal charm.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, booking an extended stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform for planning your trips. You can easily start new adventures, continue from where you previously paused, or organize your existing plans. Your saved or booked properties will be neatly categorized under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Head to the elegant 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 vacation rentals feature full kitchens and laundry facilities.

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 (1.6 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)
  • Osprey's Dominion (18.5 mi / 29.8 km)

Exploring the natural features in Madison

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Madison is a great place to get out in nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • 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 70°F.

Transportation 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 center. If you're unable to find a flight that fits your schedule, you could book a flight to New London, CT (GON-Groton - New London), which is 27.6 mi (44.4 km) away.

If you're traveling by train, you can make your way to Madison Station.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Madison?
Houses are the most popular kind of vacation rental in Madison, according to our data. Even if you have a different idea in mind, Vrbo has properties in a variety of sizes and shapes. Take a look at our options to find your ideal match.
How much does it cost to rent a vacation rental in Madison?
Length of stay, property type and time of year are some factors that can influence the price of a vacation home. Simply add your travel dates to find your perfect escape. From cozy country cottages to expansive villas, all Vrbo vacation rentals offer incredible value.
How much does it cost to rent a beach house in Madison?
Prices for beach houses in Madison can differ depending on the size and type of the property and when you're traveling. All you need to do is enter your travel dates into Vrbo and the number of guests to view your options and prices. From there you can use our filter tool to narrow your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Madison?
Yes. There are. You can pick from 48 vacation rentals that allow pets in Madison. Several of our pet-friendly vacation rentals have an outdoor space for your four-legged pal to play in, doggie beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Madison?
Add another level of fun to your trip by booking your family into one of the seven houses with a private pool in Madison. Use our search filter to find the kind of property you want on Vrbo, and then spend lazy days splashing and playing in a swimming pool that's only for you.
What are popular rental amenities in Madison?
When it comes to rental amenities that guests are searching for in Madison, an ocean view, an electric car charging station and nearby museums are the most popular. With Vrbo vacation homes, you'll have options to fit your style and taste, whether you're going on a trip with family, friends or even pets.
Are there large group vacation rentals in Madison?
Madison has 10 vacation homes that can host 10 or more guests. These stays come with the space you need to share good times with friends and family.
Are there vacation rentals in Madison that welcome kids?
Gather your entire family for the adventure of a lifetime in Madison at one of our 48 family-friendly properties. A lot of these stays come with amenities that are perfect for getaways with the little ones, including full kitchens, extra bedrooms and swimming pools. Simply click on the "Properties good for families" filter and pick your favorite.
What are the top attractions for families in Madison?
Keeping the kids happy during your vacation in Madison is easy with these awesome family-friendly attractions:

  • Hammonasset Beach
  • Hammonasset Beach State Park
  • Bishops Orchard and Winery

Are there one-bedroom vacation rentals in Madison?
You can choose from two one-bedroom rentals in Madison. Whether you want a comfy cottage or a fancy condo, our one-bedroom properties are ideal if you don't need loads of space. One of the main perks of having your own place? You'll never need to share your trip with strangers.
Can I find two-bedroom vacation rentals in Madison?
Madison has eight two-bedroom vacation properties to select from. Discover a vacation home with all the space and comfort you're looking for at a price that's hard to resist on Vrbo.
Are there vacation rentals with WiFi in Madison?
Whether you'd like to keep up with the news, look over emails or post a pic to social media, there are 26 vacation homes with WiFi in Madison. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Madison?
Choose from 45 vacation rentals with air conditioning in Madison offering that gentle, cool breeze and extra comfort level. Just enter your chosen travel dates and then take advantage of our filters to help you book properties with air conditioning.
How old do you have to be to rent a vacation rental in Madison?
The minimum required age is usually 16, 18 or 21. It can vary from property to property on Vrbo, so look at the rules of your preferred Madison stay before booking.
How long can I rent a vacation rental in Madison for?
How long you can rent a vacation rental in Madison differs according to the property. Just enter your preferred dates to display a list of options offering extended stays. With loads of features such as air conditioning and laundries, as well as some offering weekly or monthly discounted prices, you're sure to get the perfect place to call your home away from home in Madison.
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