Best Vacation Homes in Madison
New
House
9.2(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
2034 ft²
Private Pool
Fireplace/Heating
Pool
Balcony/Terrace
US $689/Night
7 Nights - US $4,822
Bed & Breakfast
9.5(91 Reviews)
11 Bedrooms
11 Baths
31 Guests
258.33 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $462/Night
7 Nights - US $3,237
Bed & Breakfast
10.0(93 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast
Pet Friendly
US $364/Night
7 Nights - US $2,549
Apartment
10.0(41 Reviews)
2 Bedrooms
1 Bath
4 Guests
600 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $432/Night
7 Nights - US $3,027
Bed & Breakfast
9.5(43 Reviews)
8 Bedrooms
8 Baths
17 Guests
410.57 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $366/Night
7 Nights - US $2,561
House
10.0(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
1108 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
US $401/Night
7 Nights - US $2,805
Cottage
10.0(23 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Kitchen
US $268/Night
7 Nights - US $1,876
House
10.0(19 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $278/Night
7 Nights - US $1,948
Madison Luxury Rentals
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Air Conditioner
US $2,390/Night
7 Nights - US $16,731
House
3 Bedrooms
3 Baths
10 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,958/Night
7 Nights - US $13,708
House
9.8(7 Reviews)
9 Bedrooms
3 Baths
20 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,950/Night
7 Nights - US $13,647
Cottage
10.0(5 Reviews)
6 Bedrooms
3 Baths
12 Guests
3040 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,586/Night
7 Nights - US $11,102
Villa
10.0(7 Reviews)
4 Bedrooms
2 Baths
10 Guests
3600 ft²
- Private Pool
- Oceanfront
Hot Tub- Fireplace/Heating
US $1,226/Night
7 Nights - US $8,581
House
10.0(18 Reviews)
4 Bedrooms
3 Baths
8 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,077/Night
7 Nights - US $7,538
House
10.0(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,053/Night
7 Nights - US $7,371
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $1,051/Night
7 Nights - US $7,358
Madison Pet Friendly Vacation Rentals
House
10.0(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $331/Night
7 Nights - US $2,318
House
4.5(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
226.04 ft²
- Balcony/Terrace
- Pet Friendly
Parking- Air Conditioner
US $746/Night
7 Nights - US $5,224
House
10.0(11 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $749/Night
7 Nights - US $5,240
Cottage
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $557/Night
7 Nights - US $3,896
House
4 Bedrooms
2 Baths
8 Guests
2034.38 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Parking
US $681/Night
7 Nights - US $4,767
Cottage
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
US $416/Night
7 Nights - US $2,914
House
10.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $323/Night
7 Nights - US $2,259
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $235/Night
7 Nights - US $1,642
Madison Large Vacation Homes
House
10.0(43 Reviews)
5 Bedrooms
2 Baths
12 Guests
4850 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $742/Night
7 Nights - US $5,195
House
10.0(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
2400 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $561/Night
7 Nights - US $3,929
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $508/Night
7 Nights - US $3,556
House
10.0(2 Reviews)
5 Bedrooms
1 Bath
10 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $838/Night
7 Nights - US $5,865
House
9.8(44 Reviews)
5 Bedrooms
3 Baths
14 Guests
3667 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $928/Night
7 Nights - US $6,495
House
9.6(43 Reviews)
6 Bedrooms
2 Baths
11 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $555/Night
7 Nights - US $3,885
New
House
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Air Conditioner
- Internet
US $1,016/Night
7 Nights - US $7,111
New
House
4 Bedrooms
4 Baths
11 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $739/Night
7 Nights - US $5,170
Why Choose Rent By Owner for your Madison Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Madison Vacation Rentals
Where are the best neighborhoods to stay in Madison?
Discover the charm of Madison, Connecticut, as you consider where to stay during your visit. This picturesque New England town offers a variety of neighborhoods, each with a unique atmosphere that caters to different travel preferences. Whether you prefer the serene seaside surroundings or the quaint, historic districts, Madison provides a welcoming environment for your vacation. Choosing a neighborhood in Madison ensures you are close to local attractions, beaches, and scenic spots, making it easy to create memorable experiences. Experience the best of this coastal community by selecting a comfortable and conveniently located vacation rental that suits your needs.
Madison Center
Staying near the heart of this destination offers convenient access to local shops and dining, providing an authentic experience of the area's charming atmosphere. Here, you'll find a variety of vacation rentals that make exploring the region effortless and enjoyable.
View 96+ Rentals in Madison CenterBest Times to Visit Madison
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this charming area can enhance your experience, as each season offers unique opportunities to enjoy the region’s scenic beauty and local ambiance.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During the late spring to early summer months, this region experiences its most vibrant and welcoming atmosphere, making it an ideal time for enjoying outdoor activities and scenic views.
Average Temperature Daytime: around 70°F to 75°F - Nighttime: around 50°F to 55°F
Early Fall (September to October)
The early fall season offers pleasant weather and stunning foliage, offering a picturesque setting perfect for exploring and relaxing in this destination's natural beauty.
Average Temperature Daytime: around 65°F to 70°F - Nighttime: around 45°F to 50°F
Off-Season Highlights
Winter (December to February)
During the winter months, the area sees fewer visitors, providing a quieter atmosphere where you can enjoy a cozy retreat amid serene surroundings.
Average Temperature Daytime: around 35°F to 40°F - Nighttime: around 20°F to 25°F
Late Autumn (November)
Late autumn is considered off-peak, when the leaves have fallen, and the region quiets down, offering a peaceful environment for those seeking solitude and tranquility.
Average Temperature Daytime: around 50°F to 55°F - Nighttime: around 35°F to 40°F
Weekly Weather Forecast for Madison
How to Book Your Madison Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Madison
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining spaces perfect for summer meals with views of the surrounding nature.
- Relax in a private backyard with lush landscaping and comfortable seating areas.
- Take advantage of a spacious deck or patio ideal for entertaining friends and family.
- Make the most of a fire pit for cozy evenings under the stars, a popular feature in the area.
- Explore well-maintained gardens that add to the natural beauty of your stay.
- Use a dedicated outdoor grilling station to prepare delicious meals during your visit.
- Stroll through scenic walking paths or access nearby outdoor recreation spots easily from here.
Top Attractions Around Madison
What attractions are nearby?
During your stay, you can enjoy a variety of outdoor activities and scenic explorations nearby, making it an ideal destination for those seeking both relaxation and adventure in this charming coastal region.
Family Activities
- Hammonasset Beach State Park: Spend a day at this popular Connecticut state park, where you can enjoy swimming, picnicking, and exploring nature along the sandy shoreline.
- Madison Art Cinemas: Experience family-friendly movies in a cozy setting, making for a perfect indoor activity during your stay here.
- Devil's Hopyard State Park: Discover hiking trails, waterfalls, and scenic views that make this outdoor destination ideal for adventurous families exploring the region.
- Madison Beach Marina: Take part in boating or paddleboarding adventures on the water, offering memorable experiences for all ages in the area.
Adult Activities
- Visit the Madison Beach Hotel: Experience luxurious seaside relaxation and scenic ocean views at this renowned hotel in the region.
- Explore Hammonasset Beach State Park: Enjoy walking along pristine sands, swimming, or picnicking at this popular Connecticut destination for outdoor enthusiasts.
- Discover local art galleries and studios: Immerse yourself in the vibrant arts scene that showcases the creative spirit of the area’s talented artists.
- Enjoy kayaking or paddleboarding on nearby waters: Engage in water sports that offer a refreshing way to explore the scenic coastline here.
Other Places to Stay in Madison, CT
Hammonasset Beach State Park
Hammonasset Beach
Meigs Point Nature Center
Madison Center
Deacon John Grave House
North Madison Shopping Center
Anna Mia's
RJ Julia Booksellers
Scranton Memorial Library
Allis-Bushnell House and Museum
Madison Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Beaches: Take advantage of the pristine shoreline by spending time at nearby beaches to enjoy relaxing seaside activities and breathtaking views.
- Visit Scenic Trails: Discover the area's natural beauty through its well-maintained hiking and biking trails, perfect for outdoor enthusiasts seeking adventure.
- Dine at Local Eateries: Savor regional flavors by dining at popular local restaurants that showcase the region’s culinary diversity.
- Plan Seasonal Activities: Align your visit with seasonal events and festivals to experience the area's vibrant community spirit and cultural offerings.
Transportation Options
- Madison Train Station: The train station offers convenient rail connections to nearby cities, making it easy for you to explore the region without hassle.
- Local Bus Services: Local bus routes provide affordable and reliable transportation options within the area, ideal for short trips around Madison.
- Rental Car Services: Several rental car agencies operate nearby, giving you the flexibility to discover the surrounding Connecticut coastline and towns at your own pace.
- Taxis and Rideshare Options: Taxis and rideshare services like Uber and Lyft are readily available here, offering a quick and comfortable way to get around during your stay.
Local Customs Options
- Traditional Clambakes: Participating in local clambakes offers a genuine taste of this region's maritime heritage, often held during community gatherings here.
- Seafood Etiquette: Respect for fresh seafood, especially oysters and lobster, is deeply rooted, and you'll find locals appreciate proper handling and dining manners at the region’s eateries.
- New England Hospitality: Warm welcomes and friendly interactions reflect the area's cherished tradition of neighborliness, making your stay more comfortable and authentic.
- Historic Preservation Customs: Appreciating the effort to maintain historical sites and architecture here shows your respect for the area's rich cultural history during your visit.
Madison Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Madison?
There are a lot of options in Madison. If you plan on staying in the Madison area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Madison:
- The Homestead
- Direct waterfront renovated cottage.
- COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
- TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12
- Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
- Ideal Madison home just steps to the beach
- Great home walkable to everything!
- Charming 2-Bedroom Ranch on a Quiet Cul-de-Sac - Minutes to Beach and Town Green
- The gardners Cottage 1 mile from long Island Sound - pet friendly
- Beautiful Beach Home and Garden Paradise
2. How many vacation rentals have private pools in Madison?
There are 7 vacation rentals with private pools near Madison. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Madison are best for families?
If you are looking for a family-friendly vacation home in Madison, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Madison:
4. How many Rentbyowner vacation rentals are available in Madison?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 187 in the Madison area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Madison.
5. What is the cancellation policy for vacation rentals in Madison, Connecticut?
Cancellation policies vary by property, so you should review the specific listing details or contact the owner directly to understand the terms and any potential fees associated with cancellations in this area.
6. How do I confirm my booking for a vacation rental in Madison, Connecticut?
Once you select your preferred property, you'll typically need to complete the reservation process on the listing page, which may include providing payment details and contacting the property owner if necessary, to ensure your booking is secure.
7. Are there any house rules or restrictions I should be aware of before booking?
Yes, each vacation rental has its own set of house rules and restrictions listed in the property details. It’s important to read these carefully and reach out to the owner if you have any questions or special requests.
8. What amenities can I expect when booking a vacation rental here?
Amenities vary from property to property, but many here offer essentials like Wi-Fi, parking, and fully equipped kitchens. Check the individual listing for specific amenities available during your stay.
9. How do I find the most suitable vacation rental in Madison, Connecticut for my needs?
You can filter search results based on your preferences, such as size, price range, and desired amenities. Additionally, reading reviews and contacting property owners can help you choose the best option for your visit to the region.
Madison Top Rated Vacation Rentals
US $131/Night
7 Nights - US $918
Boat Rental
4 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $1,047/Night
7 Nights - US $7,326
House
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $681/Night
7 Nights - US $4,766
House
10.0(68 Reviews)
4 Bedrooms
2 Baths
8 Guests
1600 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $896/Night
7 Nights - US $6,269
House
10.0(53 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $205/Night
7 Nights - US $1,438
House
10.0(14 Reviews)
2 Bedrooms
1 Bath
4 Guests
745 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $314/Night
7 Nights - US $2,195
House
10.0(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $325/Night
7 Nights - US $2,275
House
10.0(5 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $2,316/Night
7 Nights - US $16,215
