Vacation Rentals By Owner In Madison, CT

Situated on one of the premier sandy beaches on the Connecticut coastline, this house is a true gem. The owners only list it on occasion so it gets less wear and tear than other listings.brbrLocated on almost .75 lush acres, this 4-bedroom home sleeps 8 (plus a crib) and is a private oasis for just lounging around on the beach, playing in the yard with kids, or exploring Connecticut's coastal towns.brbrWalk outside and relax on one of your decks overlooking the ocean. Take a dip in the water - this exclusive beach is only accessible to the few homeowners who have houses on it. Explore nearby towns such as Guilford and Old Saybrook or spend the day in New Haven visiting the many downtown museums and shops.brbrFeatures:br- Direct beach access (only available to neighborhood homeowners and their guests)br- Two outdoor decks on the first floor and a balcony off master bedroombr- Outdoor furniture including dining table, lounge chairs and plush seating (in season)br- Covered porch overlooking the oceanbr- Gas grillbr- Central A/Cbr- Outdoor shower (in season)br- Wifibr- Full kitchen with coffee maker, blender, pots, pans, etc.br- Washer & dryerbr- DVD player with a selection of DVD'sbr- Fireplacebr- Swing set on community beach next doorbr- A selection of board games and outdoor gamesbr- Beach chairs and beach toys (in season)br- Linens including beach towelsbrbr__ BEDROOM / SLEEPING CONFIGURATION __brbrMaster Bedroom (Water Views):brKing BedbrAttached Full BathbrOutdoor BalconybrbrGuest Bedroom (Water Views):brQueen BedbrBaby Crib (not counted in total sleeping count)brbrKids Bedroom:br2 Twin BedsbrA third, trundle bed is also located in this room (but not counted in total sleeping count)brbrFirst Floor Bedroom:brQueen BedbrAttached bathroom/showerbrGreat for in-laws and older folks because of first floor locationbrbrHouse Rules:br- This property does not allow petsbr- Minimum 3 or 4 night stay (depending on season)br- Check in after 3 pm, check out by 11 ambr- This house is professionally cleaned between each guestbrbrNote: There is also a guest house on top of the garage that is sometimes occupied. When in use, the person in the guest house does not have access to the rest of the property.

Rare! Private Beachfront House in Madison CT - Sleeps 8 - Last Min Availability

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(40)

$489.9

Come stay on the closest property to Hammonasset Beach State Park in all of Madison! Just 1 mile and your feet are on the beach, with two miles of white sandy beach to relax, explore, and enjoy.brbrWalk across the street to the Greenway Trail and stroll the scenic mile of gorgeous marsh and ocean views leading to the beach, or head just 1.5 miles into downtown Madison for shops, restaurants, and charm.brbrThis peaceful 1.5-acre property includes two rentals:brbrThere is the main house and the this fully renovated, modern carriage house apartment — located just 50 feet from the main home but fully private.brbrThe apartment features:br• Private entrancebr• Fully equipped kitchenbr• Outdoor deck and fire pitbr• Separate patio with dining areabr• Beautiful yard surrounded by treesbrbrThe entire space is yours. The only shared space is the driveway.brbrWhether you're here for a romantic beach getaway or a quiet coastal retreat, you’ll love the privacy, location, and charm of this hidden gem. Book your stay today and enjoy the best of beachside Madison!

Apartment

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison, Connecticut, United States

Bed

Bath

Sleeps

$495.01

Bring the whole family to this great place with lots of room for fun. This newly-renovated home is just a short walk to Kelsey Place's private beach. There is a huge master suite with private balcony & full bath in its private wing over the 3-car garage. 3 additional bedrooms include 1 on the 1st floor with a full bath and queen bed; 2 upstairs bedrooms share a full bath (1 room with 2 twin beds, the 2nd with 1 queen). The entire house is newly-renovated with new furniture & appliances.

7 Min Walk from Water: Cheerful 4 Bedroom Home

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(5)

$476.43

Take your vacation at this newly renovated adorable cottage in a great family community, and a 4 min walk to private beach! The cottage has a brand new kitchen and bath. 3 bedrooms and an additional breezeway space perfect for reading or an additional private sleeping space. The cozy living room has a large TV, with Amazon firestick to watch your favorite streaming services. The dining area has a table ready for meals and games. The home has a large outdoor patio, with table for outdoor dining and an outdoor shower. Spend the day at the private association beach. Close to downtown Madison, the state boat launch and restaurants. brPlease note **This close knit, family community has a strict, no large gathering rule **

Newly renovated cottage in a private beach community.

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(9)

$471.72

Fully Renovated | Barbecues w/ Gas Grill | 2 Mi to Hammonasset Beach State ParkbrbrEnjoy a memorable retreat at this 3-bedroom, 3-bath vacation rental in Madison, CT! With quick access to Hammonasset Beach State Park, this 100-year-old home offers the perfect base for a comfortable coastal escape. When you're not relaxing on nearby shores, visit local hotspots like Bishop's Orchards or shop and dine downtown. After blissful days, gather around the fire pit for s’mores and captivating stories!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 full bedbr- Bedroom 3: 1 full bedbrbrOUTDOOR LIVINGbr- Private yardbr- Furnished deckbr- Fire pit (wood provided)br- Gas grillbrbrINDOOR LIVINGbr- Fireplacebr- Flat-screen TVsbr- Booksbr- Dining tablebr- En-suite bathroomsbrbrKITCHENbr- Refrigerator, stove/oven, dishwasher, microwavebr- Keurig coffee makerbrbrGENERALbr- Free WiFibr- Central A/C & heatingbr- Electric heating & window A/C unitsbr- Linens & towelsbrbrFAQbr- 2 exterior security cameras (facing out)brbrACCESSIBILITYbr- 2-story home, exterior stairs to enterbr- 1 full bathroom on 1st floorbr- All bedrooms on 2nd floorbrbrPARKINGbr- Driveway (3 vehicles)brbr-- THE LOCATION --brbr- Quiet area, 1 mile to Madison Green Historic Districtbr- 4 miles to Clinton Premium Outletsbr- 7 miles to Jacobs Beach + Bishop’s Orchards Farm Market & Winerybr- 8 miles to Chatfield Hollow State Parkbr- 11 miles to The Woodwinds - event venuebr- 18 miles to Tweed New Haven Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowed br- No events, parties, or large gatherings br- Additional fees and taxes may apply br- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires exterior stairs to enter. While it offers 1 full bathroom on the 1st floor, interior stairs are required to access all bedroomsbr- Your safety matters. This property features 2 exterior security cameras. Camera 1 is located on the garage facing the driveway. Camera 2 is located at the rear of the home facing the backyard. These cameras do not look into any interior spaces. The cameras record video and sound when activated by motion

2 Mi to Dtwn: 2-Acre Retreat w/ Large Yard!

Madison, Connecticut, United States

Bed

Bath

Sleeps

$1958.23

Centrally located, walking distance to downtown Madison, town green, & beautiful town beaches. With a private pool, large yard & gardens, this property is an ideal family retreat. This spacious & comfortable summer home enjoys a cool beach climate, comfortably sleeps 12, and is ideal for a large family or two families. The large private yard includes an outdoor grill area, hammock, fire pit & multiple relaxing garden spots. Have fun together with the ping pong/ pool table, play badminton or croquet in the yard (sets included with rental), gather together to watch movies or sports on the large screen TV (subscription separate). The open floor plan seamlessly connects the living and dining areas, both indoor and outdoor. The fully equipped kitchen offers plenty of counter space for preparing meals, the outdoor grill is convenient to the house & eating areas. Madison is a picturesque town with a rich history and plenty of local charm. Guests can easily explore the area's many attractions, including the famous RJ Julia Booksellers, Ashley's Ice Cream, restaurants, boutiques, and the local movie theater. The town green hosts summer concerts, weekly farmers markets, antique fairs, and other events, offering plenty of opportunities for entertainment and relaxation.

Madison Beach House, Private Pool, Walk to Beach & Town

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(6)

$517.5

Walking distance to the a private beach (4 houses back from the beach), classic CT shoreline cottage has air conditioning and all the amenities for the idea family vacation. Built in 1934, the house was updated in the 1970s. Large living room and enclosed sun porch accommodates family gatherings. Bedrooms are upstairs. Master has queen bed. Two additional 2 bedrooms each with two twin beds. Three additional beds available on upstairs enclosed porch (not air conditioned). Small bathroom with shower downstairs. Upstairs bathroom with bathtub. Outdoor shower in enclosed latticework to shower off sand and salt water after your day at the beach. High def flat screen TV and wifi. 10 minute drive to town and grocery store Many excellent stores restaurants in the area as well as shopping and local farms and farmers markets. .

Classic shoreline cottage 5-minute walk to the beach, Madison CT private beach

Madison, Connecticut, United States

Bed

Bath

Sleeps

$463.83

Fully furnished home with one floor living and its own private beach in a quiet neighborhood. 3 bedrooms: master with king; second with double; and third with twin beds. Two full bathrooms. Master bathroom is a brand new renovation. Bright living room with cozy bay window seat and adjoining dining room. Eat in kitchen with skylight, full appliances, and separate laundry/pantry. Spacious glass enclosed sunroom patio with dining area and ceiling fan. Large yard with deck and gas grill. Ready to move in. All cookware, linens, cable tv, and wifi provided. Kayaks, bikes and board games are available. 2 min walk to home's own private beach. 5 min drive to scenic downtown Madison. Monthly rental is preferred. Available August 2026. Contact Leslie for questions, 404-401-0469. 20 min drive to New Haven. Approximately 2 hours from New York City and Boston.

Great 3BD/2BA Sunny Ranch with Private Beach and Large Yard

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(29)

$872.08

Sleeps 8 - Fabulous summer rental in the heart of Madison, CT, this 2,741 sq ft 4-bedroom home is perfect for a family vacation. Located only a 100 yards from the beach and minutes from beautiful downtown Madison. Steps from the Madison Beach Hotel that offers spa services and 5-star dining. This updated home features a large eat-in gourmet kitchen, ideal for family entertainment. Features hot water outdoor shower, patio area, air conditioning, Tesla charger, and much more.brbrMinimum 4 nights - July & August are minimum monthly stays. brbrHome is located on a small, private road in a quiet neighborhood. Parking is limited to property which can accommodate a maximum of 3 vehicles in driveway. Large gatherings are not allowed.

Ideal Madison home just steps to the beach

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(68)

$760.89

Searching for the perfect getaway Look no further than our home on the Madison shoreline, where a private beach and the Long Island Sound are your front yard! It’s perfect for a weekend getaway or the family vacation of a lifetime — in summer AND the winter. brbrEvery room in our home has breathtaking views. Whether it’s the sight of the sun rising over the Long Island Sound, or the view of the Neck River trickling along behind the house, you’ll understand why people say that a picture is worth a thousand words. Every window in the house is broad, to provide the perfect view, and storm-resistant. brbrThe first floor is open concept with a family room, kitchen, dining area, and study. Our front deck is made of Azek and expands the width of the home for views of Falkner’s Island and Long Island Sound. We placed a rock barrier around our private beach for protection and during high tide, the water creates a private pool. brbrThe kitchen comes fully stocked with a microwave, oven, dishwasher, dishes, pots and pans, baking sheets, Keurig K-cup coffee machine, toaster, cutting boards, utensils, glasses, mugs, and platters. There are the basics to get you started, including dish soap, toilet paper, dishwasher tablets, cleaning supplies and paper towels.brThe dining area has a table with 6 chairs, though it can comfortably seat 10. We have four additional chairs available in storage. brbrThe master bedroom has a queen size bed, luxury linens, a full closet, dresser, ceiling fan, and TV. The first window overlooks the water and one of the best views of the Long Island Sound. Every morning, you will wake up to one of the most beautiful sunrises in the world. The guest room has a queen size bed, ceiling fan, a roomy closet, and has an ocean facing window. brbrThe second guest room has one full bed and one twin bed. The third guest room comes with a bunk bed that sleeps two – perfect for the young kids in your family!brbrThe house also comes with fresh linens on all the beds and bath towels for your use.brbrOne of my family’s favorite things to do is walk to Guilford’s iconic Red Shack through Grass Island. This scenic stroll takes you through a beautiful nearby beach and is just a mile away from the house. The boat launch is also found on this path. brbrMadison’s downtown area is 3.5 miles from the home. There you will find restaurants, coffee shops, the famous R.J. Julia bookstore, art galleries, cinema, unique shops, and other essentials. Drive ten minutes to outlet stores or to the Shoreline East Train that will take you to Grand Central Station, New York. Nearby tourist attractions include Thimble Island tours, Thimble Island Brewing Co., Stony Creek Brewery, Chamard Vineyards, pick your own fruits at Bishop's Orchards, Mystic Seaport and Aquarium, Submarine Force Museum in Groton, Essex Steam Train and Riverboat Ride and Hammonasset Beach State Park. Our home is also located just 4.5 miles from historic downtown Guilford. Their town center is incredibly walkable and has a variety of restaurants, from Thai to traditional New Haven pizza, for you and your family to enjoy. brbrAt our home, you will be able to enjoy the quiet serenity of a private beach while being a short drive away from New Haven and other shoreline communities. We hope that you will create some wonderful memories, as we have, at this home. brPlease see below a video from the town of Madisonbrhttps://www.elocallink.tv/m/v/Redesign4/ pid=w6wpB7z3&fp=ctmadi24_wel_iwd#c|ctmadi24_tour_iwdbrbrWe have installed exterior cameras for your safety.brbrPlease note that this house is available to book only on VRBO. br

New Madison beach house - Ocean front- Great views- booking Summer 2026

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(7)

$1127.82

Stunningly updated waterfront beach house. Water access best for boating, kayaking and paddle boarding! Never leave the house or venture out in town. Located in charming Madison, CT. Close to adorable downtown, local beaches and Hammonassett state park/beach! Home has 3 bedrooms and 1 bath. Window unit air conditioning.

Waterfront home surrounded by stunning water views.

Madison, Connecticut, United States

Bed

Bath

Sleeps

$542.14

This 3-bedroom house is perfect for your escape to Madison. Steps from the beach - beach chairs and towels included. Beautiful views of the marsh with osprey, herons, and egrets. brCan walk or bike to quaint shops and cafes in town with a famous bookstore or bike or walk along the shoreline.

3-bedroom house on the Madison, CT shore with outstanding views of marsh.

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(15)

$569.03

Built in 1937, Summersalt combines quintessential New England beach house charm with modern updates and fun, unique touches throughout. The kitchen is well-stocked with everything you might need to cook at home, including a gas range, Instant Pot, crockpot and air fryer. Warm summer evenings invite cookouts on the grill and meals on the patio. With access to the private Lee Manor beach just a 2-3 minute walk away, you'll be able to soak up the sun from a lounge chair, swim in the gentle waves of the Long Island Sound and search for seashells along a private and pristine section of shoreline in Madison.

Summersalt Madison: New England shoreline charm 2-3 minutes from private beach

Madison, Connecticut, United States

Bed

Bath

Sleeps

$393.5

Rare opportunity to rent the enchanted cottage . Situated on a peninsula with the East River on one side and Long Island sound on the other!brbrPrivate beach and access to many one block away. Madison - a picture perfect New England shoreline town.brbrThree options to rent: summer July, August '26 full month @$9000 each. 2. Full year starting June '26 @ $3600 (summer included re price). 3. Academic September'26-June 30 @ $3300/month.

AVAILABLE JULY/AUGUST & other Charming 2 bedroom bungalow 1 block to the beach.

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(7)

$776.25

Enjoy spectacular views of the Long Island Sound and East River in this newly completed house on the beach. This small but mighty house sleeps 6 comfortably and offers modern amenities and clean fresh spaces to relax and unwind.

Coastal getaway with water views in every room

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(42)

$511.75

Gorgeous, modern, beach farmhouse is waiting for you to come and enjoy! This fully renovated home has access to a private beach just 4 houses away! Open floor plan with high ceilings makes this home a retreat. This home offers 3 bedrooms, 1 full bathroom, ceiling fans, central air conditioning and an outdoor, private shower. The home has a fenced in bluestone patio with an outdoor kitchen with built in gas grill and a wood burning fire pit. There is an outdoor table with 4 dining chairs, Adirondack chairs and umbrellas.brbrThe kitchen comes fully stocked with a microwave, oven, dishwasher, dishes, pots and pans, baking sheets, Keurig K-cup coffee machine, toaster, cutting boards, utensils, glasses, mugs and platters. There are the basics to get you started including dish soap, toilet paper, dishwasher tablets, cleaning supplies and paper towels. There is a table and 5 chairs in the breakfast nook. brbrMaster bedroom has a queen size bed, luxury linens, full closet, 2 dressers, ceiling fan and TV. First guestroom has a full size bed, Pottery Barn bedding, closet and ceiling fan. Second guestroom has full size bed, Pottery Barn bedding, full closet and ceiling fan. The house also comes with fresh linens on all of the beds and bath towels for your use.brbrLiving room has TV, board games, ceiling fan, vaulted ceilings, couch, 2 overstuffed chairs and 2 Chippendale chairs. The home also has WIFI. brbrBasement has a full size washer and dryer for your convenience. brbrBeach chairs, cooler, sand toys, kayak, boogie boards, Razor scooters and beach umbrellas are all available for your use. 4 beach towels are also provided for your convenience. You can literally just pack you flip flops and bathing suits an arrive!brbrWe provide a guide book to allow you to have the most comfortable and enjoyable stay. We have 2 driveways which is rare for a shore home.brbr3 minute drive to downtown Madison, Surf Club, the Madison Beach Hotel, shops and restaurants. brbrStroll along the beach to fish or walk to the Madison Surf Club to enjoy a large playground, snack bar and public beach. Walk or bike into the town of Madison where you will find restaurants, coffee shops, the famous R.J. Julia bookstore, art galleries, cinema, unique shops and other essentials. Drive ten minutes to outlet stores or to the Shoreline East Train that will take you to Grand Central Station, New York. Nearby tourist attractions include Thimble Island tours, Thimble Island Brewing Co., Stony Creek Brewery, Chamard Vineyards, pick your own fruits at Bishop's Orchards, Mystic Seaport and Aquarium, Submarine Force Museum in Groton, Essex Steam Train and Riverboat Ride and Hammonasset Beach State Park. Our home is located just 2 miles from historic downtown Madison and 3.5 miles from downtown Guilford.brbr*** We kindly ask that you remove your shoes before entering the home and wash sand off of feet in the outdoor shower.brbr*** Important! Please shake off sand from bathing suits, towels and clothes before putting them in washing machine. The washing machine pump cannot handle sand and will seize if there is too much sand in the laundry.brbrThere is also a hose in the outside shower for your convenience, and we would kindly ask you to rinse off outside before coming in.

Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(18)

$944.64

Exceptional beach house with all the trimmings in a family neighborhood steps away from the East Wharf beach, ranked by Save the Sound as one of the best swimming beaches in CT. The home is complete with all the amenities including outdoor shower, awesome patio with a firepit and a large yard, and newly renovated bathrooms with heated floors. Enjoy walking, biking and rollerblading along the shoreline.brA short walk to downtown Madison, described as 'a hidden gem of a beach resort in Connecticut that offers a taste of Nantucket much closer to home.' Madison offers shopping, dining, ice cream shops, an independent movie cinema and RJ Julia bookstore, voted by PENN as the best in the Country. Madison's Town Green holds weekly farmer's market, summer concerts, antique shows and flea markets. It’s also home to Hammonasset Beach State Park with a two-mile sandy stretch of beach. Day trips to Providence, Newport,Rhode Island, Essex Ct Yale/NewHaven, Mystic Seaport and Aquarium to name a few local attractions.br PETS ARE ALLOWED FOR AN ADDITIONAL FEE. SLEEPS 6-8.

Newly-renovated beach house; steps to water; walk to town!

Madison, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(7)

$1949.56

Never before offered! We’ve decided to rent the “twin” of our popular vacation rental on Middle Beach Road in Madison. These two “summer cottages” were designed and built in 1918 by two brothers from Philadelphia, and became the Iconic Middle Beach Road Twins, with Private Waterfront, low tide beach and Inground Swimming Pool! This beautiful cottage sleeps 20 comfortably in 9 bedrooms. Big open living spaces with expansive views from every room. Large Waterfront beach area above seawall , then seawall ladder down to Long Island Sound, and sandy beach at lower tides.brbrThis lovely home is the perfect place for a large gathering of family and friends, with a quick walk to Madison Center & Madison Town Green…Located in the middle of Madison’s prime waterfront on Middle Beach Road.

Waterfront Estate Home - Beach and Shared Pool - West

Madison, Connecticut, United States

Bed

Bath

Sleeps

$289.64

This property has been lovingly renovated and features cathedral ceilings, hardwood floors as well as a large kitchen that cooks will love! The kitchen features a huge island that seats five people. There is one full bath with a walk-in shower. We are located in a quiet neighborhood that is approx. 4 miles from the town village, three town beaches & Hammonasset State Park. You can enjoy the many boutique shops of Madison. The area also offers lots of great dining opportunities. Enjoy Al fresco dining on the private deck. There is also a terrace with a firepit to enjoy those cool late summer and fall evenings. The lower level of the cottage has a studio apartment that we stay in when we are in town. It has it's own private entrance and terrace. The laundry room is located in the lower area and is the only shared space. **MIN 1 WEEK (6 nights) STAY FOR MO OF JULY.

SHABBY CHIC RETREAT

Madison, Connecticut, United States

Bed

Bath

Sleeps

Most popular vacation rentals in Madison

$780.36

Beautiful Beach Home and Garden Paradise

Madison, Connecticut, United States

Bed

Bath

Sleeps

$494.50

Contemporary and Stylish, 4-Bedroom, Madison CT

Madison, Connecticut, United States

Bed

Bath

Sleeps

$495.01

7 Min Walk from Water: Cheerful 4 Bedroom Home

Madison, Connecticut, United States

Bed

Bath

Sleeps

$511.75

Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio

Madison, Connecticut, United States

Bed

Bath

Sleeps

$517.50

Classic shoreline cottage 5-minute walk to the beach, Madison CT private beach

Madison, Connecticut, United States

Bed

Bath

Sleeps

$569.03

Summersalt Madison: New England shoreline charm 2-3 minutes from private beach

Madison, Connecticut, United States

Bed

Bath

Sleeps

$607.20

Chill and relax. Or remote to work from the beach.

Madison, Connecticut, United States

Bed

Bath

Sleeps

$760.89

New Madison beach house - Ocean front- Great views- booking Summer 2026

Madison, Connecticut, United States

Bed

Bath

Sleeps

$776.25

Coastal getaway with water views in every room

Madison, Connecticut, United States

Bed

Bath

Sleeps

$1173.49