Pet-friendly holiday rentals in Madison

4.97 out of 5 average rating, 118 reviews

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!

PetsWalkabilityHiking

4.94 out of 5 average rating, 297 reviews

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”.

PetsOutdoor spacesFamily

4.93 out of 5 average rating, 330 reviews

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!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Outdoor spacesPetsBarbecue

4.93 out of 5 average rating, 138 reviews

Home in Clinton

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

INSTANT BOOK: June 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug $2995 TOTAL COST 4 DAY PACKAGE: Sat 6/27 - Wed 7/1 Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

WalkabilityOutdoor spacesBeach

4.92 out of 5 average rating, 104 reviews

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.

Outdoor spacesWalkabilityCheck-in

4.99 out of 5 average rating, 942 reviews

The exterior view features a small wooden cabin surrounded by vibrant green trees. A stone path leads to a seating area, comprising four metal chairs and a table. Inside, the cozy octagonal space is lit by natural light filtering through several windows, showcasing a full-sized bed adorned with a colorful patterned quilt.

Tiny home in Norwich

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

WalkabilityPetsComfort

4.94 out of 5 average rating, 399 reviews

A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.

Cottage in Milford

Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Outdoor spacesWalkabilityCheck-in

4.98 out of 5 average rating, 113 reviews

The bungalow features a welcoming exterior with a heart-shaped decorative piece above the door. A cozy seating area with plush cushions is presented on the wooden deck, accompanied by two beach chairs, inviting relaxation outdoors. The sky above is bright and partly cloudy.

Tiny home in Guilford

Seagrass Bungalow

🌾Seagrass Bungalow is a sun filled, romantic, peaceful, back to nature, mini-home, that is exactly where you are meant to be! Private & surrounded by seagrass blowing in the breeze & cheerful birds waking you with the sunrise. Seagrass Bungalow is the perfect getaway for two & their small pup. Do yoga on the private deck, shower outdoors in the sunlight, grill local corn, have a cocktail by the firepit, or get out & walk to the cutest town green, shops, restaurants, & beach! ☀️

Outdoor spacesWalkabilityKitchen

4.78 out of 5 average rating, 106 reviews

A charming home exterior is lined with vibrant green ivy, surrounded by a lush garden area. A gravel pathway leads to the entrance, and cozy seating arrangements are visible in front of the house. Large windows allow natural light to fill the interior.

Cottage in Old Saybrook

Storybook 2 Bedroom Cottage

Enjoy a relaxing stay at this charming storybook home which has just been refreshed professionally and redesigned with unique and gorgeous antique furnishings and decor. Built in 1895, the home was re-envisioned by designer Charles Spada in the 90’s. A lovely private back yard with beautiful stone work and plantings. The proximity to shopping, galleries, restaurants and Old Saybrook, Town Beach and Katherine Hepburn theater makes this location ideal.

WalkabilityPetsIndoor spaces

4.96 out of 5 average rating, 187 reviews

The exterior of the historic barn is featured, showcasing weathered wood siding and a welcoming entrance with double doors. The structure is surrounded by trees and a gravel pathway leading to the front door. Soft morning light highlights the natural beauty of the setting.

Barn in Essex

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Outdoor spacesWalkabilityKitchen

4.92 out of 5 average rating, 109 reviews

A living area features a comfortable sectional sofa adorned with decorative pillows. Two light blue armchairs are positioned beside a small table with a patterned top, while a television stand and a floor lamp complete the inviting space. Sunlight is visible through a window.

Home in Old Saybrook

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

WalkabilityOutdoor spacesAccess

4.99 out of 5 average rating, 170 reviews

A bright and airy living area features large windows allowing natural light to filter in. A wooden coffee table displays various books, complemented by a bouquet of flowers. Seating includes a light-colored armchair and a sofa adorned with patterned cushions, while a dining area is visible in the background.

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 spacesBackyard

Popular amenities for Madison pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.84 out of 5 average rating, 147 reviews

The living room features a modern design with a curved green and orange sofa surrounding a light wood coffee table. A striking black fireplace provides a focal point against a light wall. A statue and decorative elements contribute to the welcoming ambience.

Home in West Haven

Westshore Luxury

Outdoor spacesWalkabilityDecor

5 out of 5 average rating, 142 reviews

Home in Milford

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

PetsWalkabilityBiking

4.99 out of 5 average rating, 177 reviews

A contemporary lakefront home is surrounded by tall trees, with a spacious deck offering views of Middle Bolton Lake. A fire pit is situated on a stone patio, surrounded by Adirondack chairs. The lush green yard leads to the water's edge, enhancing the natural ambiance.

Home in Vernon

Luxe Bolton Lake

Outdoor spacesWalkabilityBarbecue

4.8 out of 5 average rating, 142 reviews

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

PetsOutdoor spacesAir conditioning

4.97 out of 5 average rating, 192 reviews

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

Outdoor spacesPetsSleep quality

4.88 out of 5 average rating, 122 reviews

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!

WalkabilityOutdoor spacesWi-Fi

4.89 out of 5 average rating, 148 reviews

The exterior of a charming Dutch colonial house features a white facade framed by vibrant green trees and seasonal foliage. A white picket fence encloses the manicured lawn, while a walkway leads to the front porch that is accented by shutters and a welcoming entrance.

Home in Kent

Kent village home 2 hrs from NYC

PetsOutdoor spacesKitchen

4.97 out of 5 average rating, 151 reviews

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 spacesBiking

Pet-friendly home rentals with a pool

4.99 out of 5 average rating, 120 reviews

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

Home in Montauk

3 BR/Pool. Walk to Beach & Town!

PetsOutdoor spacesLaundry

4.92 out of 5 average rating, 128 reviews

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

Home in Springs

Private & Pristine with Pool and Kid’s Playard

Outdoor spacesWalkabilityFamily

4.83 out of 5 average rating, 111 reviews

The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.

Home in Litchfield

The Getaway-HOST & Co.

PetsOutdoor spacesLayout

4.84 out of 5 average rating, 121 reviews

Apartment in Burlington

Charming apartment with breathtaking view!

PetsOutdoor spacesAccess

4.82 out of 5 average rating, 131 reviews

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

Home in Springs

East Hampton Oasis - Pool and Hot Tub

Outdoor spacesWalkabilityComfort

4.88 out of 5 average rating, 126 reviews

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 spacesWalkabilityParks

5 out of 5 average rating, 183 reviews

A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

PetsWalkabilityGetting around

4.98 out of 5 average rating, 137 reviews

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

Home in East Hampton

Explore the Water & Woods at a Relaxing Retreat

Outdoor spacesPetsCheckout

Private, pet-friendly home rentals

4.89 out of 5 average rating, 54 reviews

A charming two-story house is set on a green lawn, featuring white siding and dark green shutters. Gravel pathways lead to the entrance, and a small shed is visible to the side. Mature trees provide shade, enhancing the peaceful outdoor setting.

Home in Madison

Cozy beach cottage close to everthing

Outdoor spacesPetsFamily

4.98 out of 5 average rating, 90 reviews

The exterior of The Barn features a modern design, with a wood-paneled facade and large windows set under a sloping roof. A bench is positioned on the grass nearby, surrounded by greenery and trees, providing a tranquil outdoor space.

Guesthouse in Madison

The Barn by the Sound

Outdoor spacesWalkabilitySleep quality

4.97 out of 5 average rating, 86 reviews

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

WalkabilityPetsCleanliness

4.88 out of 5 average rating, 147 reviews

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

PetsOutdoor spacesHospitality

4.95 out of 5 average rating, 226 reviews

The cabin is nestled among tall trees next to a flowing creek. Natural rock formations surround the water, creating a serene setting. Sunlight filters through the leaves, casting dappled shadows on the cabin's exterior, which features large windows that overlook the creek.

Cabin in New Milford

Creekside Cabin with Wood Fired Hot Tub & Firepit

PetsWalkabilityComfort

4.99 out of 5 average rating, 163 reviews

A charming red exterior features white window treatments and a rustic door. Decor elements include a wooden wagon wheel and an artistic iron wall hanging. Lush greenery and flowers are visible in the garden area, enhancing the welcoming entryway.

Guesthouse in Newtown

Guest Suite at Wisteria Gardens

Outdoor spacesWalkabilityAccess

4.91 out of 5 average rating, 67 reviews

Home in Madison

Coastal getaway with water views in every room

Outdoor spacesWalkabilityBathroom