Madison holiday lettings

We found 412 holiday rentals — enter your dates for availability

Select from 32 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:13 Mar - 20 Mar

Image gallery for 2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

Beach
9.8 out of 10, Exceptional, (48 reviews)
Exceptional
(48 reviews)

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

Old Lyme, CT

8% off
Price is £1,551
for 7 nights, 1 cottage
£222 per night
includes taxes & fees
2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

Find spaces that suit your style

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:

  • 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)
  • The Old Field Vineyards (17.7 mi / 28.4 km)
  • Lenz Winery (19 mi / 30.5 km)
  • Raphael Winery (19 mi / 30.6 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)
  • Guilford Town Green (5.6 mi / 9 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, the most appealing area to stay in is the charming downtown district. This vibrant neighbourhood offers a delightful mix of boutique shops, cosy cafes, and a friendly space that makes it superb for leisurely strolls. Additionally, you're just a stone's throw away from the stunning Madison Town Green, which is a lovely spot for picnics and community events.

Another excellent option is the neighbourhood of West Madison, which boasts beautiful coastal views and proximity to the picturesque Hammonasset Beach State Park. This park is a fantastic destination for outdoor enthusiasts, offering sandy beaches, hiking trails, and opportunities for birdwatching. In both areas, you can find a variety of holiday rental properties, with several options available to suit different preferences and budgets.
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, Connecticut, travellers should consider the scenic areas along the Long Island Sound. The neighbourhood around Hammonasset Beach State Park is particularly popular, offering easy access to sandy beaches and picturesque coastal views. Many properties in this area feature amenities such as private decks, outdoor grills, and spacious living areas, making them ideal for families or groups looking to enjoy seaside relaxation.

Additionally, the shoreline near East Wharf Beach provides further options, where charming beach cottages often come equipped with modern conveniences like fully stocked kitchens and laundry facilities. This area allows for quick access to local attractions, including quaint shops and restaurants in Madison's town centre, enhancing the holiday experience.
What is the most popular type of holiday rental accomodation in Madison?
In Madison, holiday houses are the most popular type of rental accommodation, with around 24 available throughout the charming coastal town. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and private outdoor areas, making them ideal for families or groups looking to enjoy the area's natural beauty and local attractions. Additionally, several cottages and apartments are offered, providing a cozier alternative for couples or smaller parties. Cottages often come with quaint interiors and delightful gardens, while apartments are conveniently located near the vibrant downtown area, where visitors can explore shops and restaurants.
Are there any family house rentals in Madison?
In Madison, Connecticut, there are numerous family-friendly house rentals available, with around 25 options to choose from. This charming coastal town offers a range of properties that cater well to families. Many homes feature spacious living areas, fully equipped kitchens superb for preparing family meals, and outdoor spaces where children can play safely.
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. This picturesque coastal town offers a charming atmosphere with its beautiful beaches and scenic parks. Many of the holiday rentals come equipped with private pools, hot tubs, and outdoor entertainment areas, making them ideal for relaxation and family gatherings. Travellers can also expect amenities such as fully equipped kitchens, spacious living areas, and access to outdoor patios or decks, enhancing the overall comfort of their stay.
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, Connecticut, there are several pet-friendly house rentals available, with around twelve options to choose from. These holiday homes often feature amenities such as spacious backyards, modern kitchens, and comfortable living areas, making them ideal for families travelling with pets. Many properties are located near the picturesque shoreline, providing easy access to sandy beaches and scenic walking paths.
Are there any remote work holiday rentals in Madison?
In Madison, Connecticut, there are numerous remote work holiday rentals available, with around 33 options for travellers seeking a conducive environment for working remotely. These properties are well-equipped with essential amenities such as reliable Wi-Fi, dedicated office spaces with desks and chairs, and comfortable living areas that provide a productive atmosphere. 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 rental amenities include a well-equipped kitchen featuring essentials like a microwave, dishwasher, and refrigerator, allowing guests to prepare their own meals with ease. Many properties also provide cookware, dishware, and utensils, making it convenient for travellers who prefer a home-cooked experience.
When is the best time to visit Madison for a holiday rental?
July is the most popular time to visit Madison, Connecticut, when the summer season is in full swing. During these months, from June to August, the town buzzes with activity as families, couples, and adventure seekers flock to enjoy its charming coastal scenery and vibrant community events. The warm weather, typically ranging from the mid-20s to low 30s Celsius, makes it ideal for outdoor activities such as beach outings, hiking, and exploring local parks.

If you're looking for a more tranquil experience, consider visiting in December. While this marks the low season, the holiday spirit brings a unique charm to Madison. You can enjoy festive decorations, quaint shops, and holiday markets while avoiding the summer crowds. Plus, this time of year often features lower rental rates, allowing you to enjoy the area's beauty without breaking the bank.
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 variety of attractions that showcase the town's coastal charm and natural beauty. The picturesque Madison Town Green serves as a central hub, surrounded by quaint shops, cafes, and local eateries, making it a superb spot to relax and soak in the community atmosphere.

Just a short drive away, Hammonasset Beach State Park offers stunning views of Long Island Sound, with miles of sandy beach ideal for sunbathing and swimming. The park also features walking trails and picnic areas, making it a great destination for outdoor enthusiasts.

For those interested in history, the historic district, with its beautiful historic architecture, provides a glimpse into the town's past. The Madison Historical Society offers insights into local history and heritage.
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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