Madison holiday homes

We found 430 holiday rentals — enter your dates for availability
Select from 36 homes, 12 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:18 Dec - 25 Dec

Dining
Exterior
Interior
Room
Exceptional
(68 reviews)

Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

Westbrook

8% off
NZ$12,547
for 7 nights, 1 home
NZ$1,792 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
3rd Guest Bedroom - Queen Size - Harbor Views
You will love the Center Island cooktop open kitchen & beautiful water views
Cozy seating area with dual water views
Sunsets are simply breath taking over the water
Exceptional
(73 reviews)

Waterfront Retreat, Private Beach + Hot Tub Sunsets

Branford

15% off
NZ$18,139
for 7 nights, 1 home
NZ$2,591 per night
includes taxes & fees
Waterfront Retreat, Private Beach + Hot Tub Sunsets
Exterior
Exterior
Exterior detail
Beach
Wonderful
(59 reviews)

2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT

Old Lyme

8% off
NZ$4,381
for 7 nights, 1 cottage
NZ$626 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Kitchen
Front of House
Side of House with outdoor shower to rinse off from the beach.
Aerial view of back deck area
Exceptional
(11 reviews)

4 BED/2 BATH -PRIVATE BEACH: OLD COLONY

Old Lyme

7% off
NZ$8,426
for 7 nights, 1 home
NZ$1,204 per night
includes taxes & fees
4 BED/2 BATH -PRIVATE BEACH: OLD COLONY
Property grounds
Property grounds
Dining
Kitchen
Exceptional
(17 reviews)

Cornfield Point Cottage

Old Saybrook

8% off
NZ$14,426
for 7 nights, 1 home
NZ$2,061 per night
includes taxes & fees
Cornfield Point Cottage
Home from the water. (Blue house in center of photo)
Interior
Living area
(new photo 6/25/2011)
Exceptional
(54 reviews)

Beautiful Waterfront Beach House for Family Vacations

Branford

8% off
NZ$10,632
for 7 nights, 1 home
NZ$1,519 per night
includes taxes & fees
Beautiful Waterfront Beach House for Family Vacations
Kitchen
Back deck
Interior
Living room, bathed in morning light
Wonderful
(90 reviews)

Historic New England home ,Reunions Beach pass

Guilford

8% off
NZ$7,054
for 7 nights, 1 home
NZ$1,008 per night
includes taxes & fees
Historic New England home ,Reunions Beach pass
Living area
Winter afternoon from the boathouse
Full chef's kitchen with new appliances
Ipe deck in the morning sun
Exceptional
(6 reviews)

Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet

Old Lyme

16% off
NZ$10,411
for 7 nights, 1 home
NZ$1,487 per night
includes taxes & fees
Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet
Room
Beach
Living area
Private kitchen
Exceptional
(32 reviews)

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

Clinton

11% off
NZ$6,784
for 7 nights, 1 home
NZ$969 per night
includes taxes & fees
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Newly remodeled kitchen
Beautiful sun room for dining
family room
family room
Exceptional
(27 reviews)

Make Memories in Charming Hawk's Nest Beach!

Old Lyme

8% off
NZ$4,370
for 7 nights, 1 home
NZ$624 per night
includes taxes & fees
Make Memories in Charming Hawk's Nest Beach!
Room
Dining
Living area
Exterior
Exceptional
(47 reviews)

Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

Westbrook

6% off
NZ$5,584
for 7 nights, 1 home
NZ$798 per night
includes taxes & fees
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
Exterior detail
Exterior
Interior
Living area
Exceptional
(56 reviews)

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

Old Lyme

8% off
NZ$3,402
for 7 nights, 1 cottage
NZ$486 per night
includes taxes & fees
2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Island's End Golf and Country Club (16.5 mi / 26.5 km)
  • Powder Ridge Mountain Park and Resort (16.6 mi / 26.7 km)
  • Kontokosta Winery (16.6 mi / 26.7 km)
  • Croteaux Vineyards (18.7 mi / 30.1 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)
  • 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)
  • East Haven Town Beach (15.6 mi / 25.1 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.
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.
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 Bookabach.
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.
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.
Are all fees included in the Madison holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Madison holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Madison holiday homes?
You can find great discounts on holiday homes in Madison on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Madison holiday home booking on Bookabach?
To find Madison holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Madison?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Madison holiday home?
Book your Madison holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Madison?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Madison to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.