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Pet-friendly holiday rentals in Madison

Find and book unique pet-friendly homes on Airbnb

Quick stats about holiday rentals that are pet-friendly in Madison

  • Total holiday rentals

    Explore 50 holiday rentals in Madison

  • Nightly prices starting at

    Madison holiday rentals start at $192 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,770 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Madison holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Madison rentals

  • 4.9 Average rating

    Madison stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Madison

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
A charming exterior view of the newly renovated carriage house is presented, featuring a wooden staircase leading to the entrance. A round table with black chairs is shaded by a vibrant red umbrella, surrounded by a green lawn and mature trees.
Apartment in Madison

Modern Carriage House Near Beach - Deck + Fire Pit

Come stay on the closest property to Hammonasset Beach State Park in all of Madison! Just 1 mile and your feet are on 2 miles of white sandy beach to explore and enjoy. This fully renovated carriage house is nestled on a grassy 1.5-acre property near town. Enjoy your own private entrance, full kitchen, sunny deck, fire pit, and outdoor dining space. Located across from the Greenway Trail and close to shops, restaurants. Ideal for couples or small families looking for a relaxing coastal getaway!

WalkabilityOutdoor spacesAir conditioning

4.98 out of 5 average rating, 125 reviews
Top Guest favourite
The sunroom features a light pink wall and a high ceiling with exposed beams. A comfortable wicker sofa with decorative throw pillows accompanies two matching chairs. A patterned area rug covers the floor, while a small table sits in the center. Soft light filters through sheer curtains.
Cottage in Guilford

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

WalkabilityPetsCheck-in

4.94 out of 5 average rating, 310 reviews
Top Guest favourite
A two-story home features a light-colored exterior with traditional shutters and a welcoming front porch. The yard is neatly landscaped with greenery and flowers. A wooden deck is visible at the back, providing an inviting outdoor space.
Home in Old Saybrook

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

WalkabilityOutdoor spacesAir conditioning

4.97 out of 5 average rating, 146 reviews
Superhost
A wooden dock stretches over the calm waters, supported by several sturdy posts featuring black caps. The sky above is clear with soft clouds, enhancing the serene coastal atmosphere.
Home in Old Saybrook

Steps to Beach! *Cozy Cottage* Pet Friendly

Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

WalkabilityOutdoor spacesBathroom

4.93 out of 5 average rating, 107 reviews
Guest favourite
The red yurt is set among tall trees, showcasing a spacious wooden deck surrounded by a lattice railing. Large windows allow natural light to enter, while the soft curves of the yurt blend harmoniously into the wooded landscape.
Yurt in Guilford

Hartwoods Yurt

Enjoy a unique wilderness getaway and unwind in a peaceful, 10.3 acre wooded environment in our 30’ diameter Yurt, which sleeps 4 in North Guilford, CT. This elevated cylindrical dwelling offers solitude and a large deck with comfortable chairs and forest views. Shaded and cool in the summer with air conditioning and fans available. This Yurt provides a wonderful respite from the hectic world. Perfect for nature lovers with a nearby brook and miles of trails for hiking and mountain biking.

PetsOutdoor spacesTV

4.88 out of 5 average rating, 153 reviews
Guest favourite
A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.
Home in Mattituck

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

PetsOutdoor spacesWi-Fi

4.93 out of 5 average rating, 138 reviews
Top Guest favourite
Home in Branford

Steps to Beach • Hot Tub • Game Room • Water Views

Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.

WalkabilityPetsNearby

4.99 out of 5 average rating, 113 reviews
Guest favourite
A bright kitchen space is highlighted by pale blue cabinetry and rich wooden countertops. A wooden table with chairs sits at the center, adorned with a vase of flowers. Large windows allow natural light to illuminate the area, enhancing its inviting feel.
Home in Guilford

Purple Button Factory Sleeps 8, Walk to Town Green

Close to CT shoreline. 4 bdrm, 2 bath, 2,200 sq ft home on dead-end street, across from Meadow River, tidal marsh. Great bird-watching! Mid-week specials. Walk to Guilford Town Green, restaurants, shopping. Fully-equipped kitchen. Wood-burning fireplace. Clean, airy, peaceful space. Eclectic art & beach-comber decor. Large back yard with fire pit. Deck for functions, family gatherings, relaxing. Historic property was once a button factory! Original chestnut, wide-board floors.

PetsWalkabilityHeating

4.75 out of 5 average rating, 167 reviews
Superhost
Cottage in Branford

Cozy 2 Story Cottage in Short Beach Community

A cozy home in a beach community that has a central location with easy access to outdoor activities & local restaurants. The home is also 5 minutes from the Branford Train Station, Stony Creek Brewery, & Branford's town center. We are also a 10 minute drive from New Haven, home to Yale University, Yale Hospital and other colleges/universities. Our guests also gain access to Johnsons' Beach, a private residents only beach, located just around the corner from the home (3 minute walk)

Outdoor spacesPetsValue

4.85 out of 5 average rating, 271 reviews
Top Guest favourite
The exterior of a private guest house is depicted, showcasing a blue facade complemented by multiple windows. A spacious stone patio features outdoor seating surrounded by lush greenery and garden flowers. The roof is sloped, and trees provide a natural canopy overhead.
Guesthouse in Guilford

Page Guest House

Updated, private detached guest house in the center of Guilford's historic district just steps from the town center. The guest house is completely renovated. Walk to everything including shops and restaurants. Town Beach and doc are just under 1.5 miles away. The second bedroom has a twin bed. You have to walk through twin room to get to master. Apartment is one floor with no steps. Bathroom is tiled and shower is walk in with no lip or tub and is easily accessible.

PetsOutdoor spacesBiking

4.98 out of 5 average rating, 116 reviews
Guest favourite
A charming cottage exterior features white clapboard siding and dark blue shutters. A sloped asphalt roof and a front door with decorative glass provide focal points. Landscaped greenery and a gravel pathway enhance the welcoming entrance, surrounded by trees that offer natural shade.
Guesthouse in Clinton

The Gardener's Cottage Dog friendly/weekly/monthly

The Gardener's Cottage, less then a mile from the Long Island Sound, is a great alternative to the common hotel. Situated a stones throw from Hammonasset State Park and Beach, Clinton Outlets, and the Shore Line East train station. Near by you will find places to kayak, Chamard Wineries, Marinas and many quaint New England towns. The Cottage is fitted with it's own router coupled with an eating nook that can double as a work space. Pets are allowed. Self check-in

Outdoor spacesPetsFamily

4.94 out of 5 average rating, 254 reviews
Top Guest favourite
Cottage in Guilford

"Red House on the Knoll" at Indian Cove

Ecape to the charming beach community of Indian Cove in Guilford and unwind in this beautifully renovated 1920s coastal cottage. Full of character and warmth, this spacious retreat blends historic charm with modern comfort-featuring wood floors, high beam ceilings, and a stunning stone fireplace that creates the perfect cozy atmosphere year round.

PetsOutdoor spacesHiking

4.99 out of 5 average rating, 179 reviews

Popular amenities for Madison pet-friendly home rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favourite
An aerial view captures the neighborhood alongside Cedar Beach, displaying rows of houses with sandy beach access. Green marshland stretches out behind the homes, while a blue sky with scattered clouds frames the serene coastal scene.
Home in Milford

Chic Beach Bungalow - Amazing Sunsets!

PetsOutdoor spacesAmenities

4.88 out of 5 average rating, 136 reviews
Top Guest favourite
A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.
Home in East Haddam

Romantic Getaway at The Lake!

Outdoor spacesPetsCondition

4.93 out of 5 average rating, 362 reviews
Top Guest favourite
A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.
Home in Milford

The ARLO - Walk to Brewery & Restaurants

Outdoor spacesPetsHospitality

4.99 out of 5 average rating, 194 reviews
Top Guest favourite
A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.
Home in Milford

3 Bedroom Beach House with Hot Tub!

WalkabilityOutdoor spacesDecor

4.97 out of 5 average rating, 158 reviews
Guest favourite
A serene outdoor space is presented, featuring two black adirondack chairs positioned on a well-maintained lawn. Colorful flower pots are placed on either side of a small table, with lush greenery surrounding the area and a tranquil lake visible in the background.
Home in Westbrook

The Dragon Fly Garden

Outdoor spacesWalkabilityHiking

4.8 out of 5 average rating, 147 reviews
Guest favourite
A two-story farmhouse presents a blend of modern and vintage elements, accented by a red front door. The surrounding landscape features a large tree and a grassy area, with additional outbuildings visible in the background, contributing to a serene rural setting.
Home in Haddam

Charming 1806 farm house close to the CT River.

Outdoor spacesWalkabilityCheck-in

4.93 out of 5 average rating, 161 reviews
Guest favourite
The image presents a serene beach scene, featuring a sandy pathway leading to a calm water body. A safety barrier is visible in the water, marking designated swimming areas. Lush green grass borders the beach, enhancing the tranquil coastal environment.
Home in Westbrook

Zion's Light Beach Cottage

Outdoor spacesPetsAir conditioning

4.89 out of 5 average rating, 101 reviews
Top Guest favourite
Home in Milford

Fully renovated/Walk to water & shops/fenced yard!

Outdoor spacesPetsBathroom

4.98 out of 5 average rating, 162 reviews

Pet-friendly home rentals with a pool

Guest favourite
The large two-tiered deck is illuminated with soft lighting, creating a cozy atmosphere. A staircase leads to the upper level, where seating and decor are visible. An above-ground pool is situated beside the deck, surrounded by greenery and evening skies.
Home in Montville

Casino Wine Down House w/Pool, Game Room, Big Deck

WalkabilityPetsValue

4.92 out of 5 average rating, 333 reviews
Superhost
A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.
Home in Sag Harbor

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Outdoor spacesPetsBeach

4.86 out of 5 average rating, 139 reviews
Superhost
A hot tub is situated on a stone patio, surrounded by lush greenery. A short set of steps leads up to its edge, and vibrant flowers add a splash of color in the background. The hot tub's cover is partially open, revealing inviting water.
Home in Montville

Walk to Casino with POOL+HOT TUB

WalkabilityOutdoor spacesBeach

4.88 out of 5 average rating, 260 reviews
Guest favourite
A spacious living room is highlighted by a unique whale wall art piece and a cozy seating arrangement. A comfortable gray sofa is paired with a nautical-themed chair. Large windows allow natural light to fill the room, creating a welcoming atmosphere.
Home in New London

Beauty and the Beach!

WalkabilityOutdoor spacesCheckout

4.89 out of 5 average rating, 175 reviews
Top Guest favourite
A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.
Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

WalkabilityOutdoor spacesLayout

4.96 out of 5 average rating, 222 reviews
Guest favourite
A bright living area is furnished with a leather sofa and a dark coffee table, positioned on a textured rug. Natural light filters through large windows, illuminating the space. A staircase leads to an upper level, with wooden accents enhancing the modern design.
Home in Bridgehampton

Central Private Bridgehampton Home

Outdoor spacesWalkabilityCheckout

4.93 out of 5 average rating, 109 reviews
Superhost
The exterior of a Cape Cod style beach house is captured at sunset, showcasing a spacious upper balcony with an umbrella and illuminated railings. The warm hues of the sky enhance the inviting atmosphere of the home, while surrounding trees add to the serene setting.
Home in New London

Sunset Oasis 1 @ Ocean Beach: $1Mil View 6 Queen

WalkabilityPetsLong stay

4.92 out of 5 average rating, 216 reviews
Guest favourite
A serene view of the pool is presented, framed by lush greenery and vibrant plant life. The clear water reflects the sky, while distant hills and a pond are visible at the horizon, creating a peaceful outdoor retreat.
Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

WalkabilityOutdoor spacesShared spaces

4.93 out of 5 average rating, 213 reviews

Private, pet-friendly home rentals

Top Guest favourite
A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.
Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

PetsWalkabilityBackyard

4.98 out of 5 average rating, 184 reviews
Guest favourite
Home in Madison

Coastal getaway with water views in every room

Outdoor spacesWalkabilityAmenities

4.9 out of 5 average rating, 70 reviews
Top Guest favourite
Home in Clinton

The Connecticut Cottage | Historic Modern Charm

Outdoor spacesPetsValue

4.97 out of 5 average rating, 32 reviews
Guest favourite
A spacious living area features large windows that allow natural light to fill the room. Neutral-coloured furnishings, including a sectional sofa and a sleek wooden TV console, create an inviting space. Decorative elements, such as a geometric wall art piece, enhance the modern aesthetic.
Home in Guilford

Beach Sanctuary on the Long Island Sound

WalkabilityOutdoor spacesLocation

4.94 out of 5 average rating, 63 reviews
Top Guest favourite
A charming cottage with a light-colored exterior sits in a manicured yard. The structure features multiple windows that allow natural light to fill the space. A small staircase leads to the entrance, surrounded by greenery and decorative landscaping, providing a welcoming facade.
Guesthouse in Madison

The Rising Tide Cottage

WalkabilityPetsGetting around

4.97 out of 5 average rating, 98 reviews
Guest favourite
The lake house features a spacious deck overlooking the water, with a private dock extending into the lake. Surrounded by lush greenery, the home has multiple outdoor seating areas and provides easy access to kayaks and boats, enhancing the scenic lakeside environment.
Home in Clinton

Boulder Lake House Retreat

Outdoor spacesPetsAmenities

4.91 out of 5 average rating, 46 reviews
Top Guest favourite
Home in Guilford

Guilford Field House

Outdoor spacesPetsNearby

5.0 out of 5 average rating, 40 reviews
Guest favourite
A serene waterside view is presented from the deck, showcasing the calm waters, dotted with small boats. Rocky shorelines and lush greenery line the opposite bank, under a clear blue sky. A patio area with chairs can be seen below the deck.
Cottage in Guilford

Waterfront Cottage With Unforgettable Views

WalkabilityOutdoor spacesAccess

4.96 out of 5 average rating, 54 reviews

When is the best time to visit Madison?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$498 NZD$519 NZD$514 NZD$524 NZD$611 NZD$587 NZD$563 NZD$591 NZD$494 NZD$489 NZD$454 NZD$496 NZD
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