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Pet-friendly holiday rentals in Madison

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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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Rental unit in East Haddam

4.78 out of 5 average rating, 274 reviews

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

Guest favourite

Cottage in Guilford

4.93 out of 5 average rating, 264 reviews

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”.

Home in East Haven

4.88 out of 5 average rating, 217 reviews

Beach Cottage by the Sea

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

Guest favourite

Cottage in Westbrook

4.88 out of 5 average rating, 127 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Guest favourite

Bungalow in Woodmont

4.98 out of 5 average rating, 268 reviews

Fall Sale!Beach Bungalow |Pet-friendly|WalktoBeach

Welcome to the Beach Bungalow, completely remodeled to the studs in '21! This Woodmont by the Sea home is a 3 block stroll to Anchor Beach & the walkway along beautiful Beach Ave. The home offers a modern kitchen, dining for 6, private back porch & outdoor shower. This +775sf bungalow has a driveway & on-street pkg. It's located in a charming coastal town, walking distance to restaurants, grocery store & Robert Treat Farm and is 2 mi to I95, 10 mi to Yale/New Haven...and mins to breweries.

Guest favourite

Home in East Haddam

4.94 out of 5 average rating, 157 reviews

Romantic Getaway at The Lake!

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 Hartford, 30 minutes from the Mohegan Casino.

Guest favourite

Home in East Lyme

4.97 out of 5 average rating, 122 reviews

Walk to the beach at Black Point, Niantic, Ct

Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Cabin in East Haddam

4.89 out of 5 average rating, 627 reviews

Postcard Cabins Machimoodus - NYC/Boston

An easy drive from the city, Postcard Cabins, formerly Getaway, is the ultimate way to experience the great outdoors. Nestled across acres of private woodlands, our tiny cabins have everything you need (AC/Heat, en-suite bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you disconnect from the everyday. As part of your stay, you'll receive a complimentary allocation of provisions, like s’mores, coffee and more.*

Guest favourite

Guest house in Portland

4.99 out of 5 average rating, 149 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Guest favourite

Rental unit in Old Saybrook Center

4.96 out of 5 average rating, 120 reviews

Convenient and Cute in Downtown Old Saybrook

Welcome to Old Saybrook! Our apartment sits over our garage and is attached to our primary residence. It is conveniently located within walking distance to Main Street, the beach, local parks, and other town attractions. We have recently made many upgrades to the property and we're ready for guests! We look forward to sharing our home with you! **PETS: DOGS ALLOWED BY PRE-APPROVAL ONLY and ADDITIONAL $25 PET CLEANING FEE. Please see House Rules for more info.

Guest favourite

Barn in Essex

4.97 out of 5 average rating, 143 reviews

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.

Guest favourite

Loft in Essex

4.94 out of 5 average rating, 429 reviews

Unique apartment in former art gallery.

The apartment is private and in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. We gladly welcome clean, well behaved pets for an extra fee of $50. Pet sitting and dog walking also available for an additional fee. On site babysitting also available for an additional fee.

Holiday rentals for every style

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Quaint homes, peaceful surroundings

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Popular amenities for Madison pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Guest favourite

Home in Fairfield

4.97 out of 5 average rating, 103 reviews

Family Xmas Bliss:Tree, Cozy fireplace & hot cocoa

Home in Washington

4.85 out of 5 average rating, 197 reviews

Country Home on a Hill

Guest favourite

Home in North Haven

5 out of 5 average rating, 134 reviews

Luxury Stay in Expansive Historical Home

Guest favourite

Home in Old Saybrook

4.97 out of 5 average rating, 118 reviews

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

Guest favourite

Home in North Fork

4.93 out of 5 average rating, 117 reviews

Modern Farmhouse Steps to Beach & Love Lane

Guest favourite

Home in North Fork

4.98 out of 5 average rating, 131 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Guest favourite

Home in Litchfield

4.93 out of 5 average rating, 177 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Guest favourite

Home in New Haven

4.97 out of 5 average rating, 159 reviews

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

Pet-friendly home rentals with a pool

Guest favourite

Bungalow in East Hampton

4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

Guest favourite

Bungalow in Montauk

4.9 out of 5 average rating, 574 reviews

Montauk Oceanview with Fireplace (2)

Guest favourite

Cottage in Montauk

4.92 out of 5 average rating, 159 reviews

Montauk Cottage Escape

Guest favourite

Home in East Hampton

4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 140 reviews

Heated pool, games room, near beach, kid-friendly

Guest favourite

Home in Sag Harbor

4.95 out of 5 average rating, 115 reviews

Sag Harbor Village Cottage with Pool

Guest favourite

Rental unit in Glastonbury

4.9 out of 5 average rating, 423 reviews

Quiet 2 bed room apt w/ private entrance.

Guest favourite

Home in Montville

4.95 out of 5 average rating, 128 reviews

Casino Stay & Play House

Private, pet-friendly home rentals

Guest favourite

Barn in Madison

4.96 out of 5 average rating, 46 reviews

Cozy Restored barn near beaches

Guest favourite

Rental unit in Guilford

4.97 out of 5 average rating, 60 reviews

Cozy Private Lake Q Retreat

Guest favourite

Guest house in Madison

4.99 out of 5 average rating, 73 reviews

The Barn by the Sound

Guest favourite

Cabin in New Milford

4.95 out of 5 average rating, 138 reviews

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Guest favourite

Cottage in East Lyme

4.97 out of 5 average rating, 267 reviews

Your Nest Near The Beach

Guest favourite

Rental unit in Middletown

4.82 out of 5 average rating, 154 reviews

Lakeside apartment 2.5 miles from Wesleyan campus!

Guest favourite

Guest house in Guilford

4.99 out of 5 average rating, 83 reviews

Page Guest House

Guest favourite

Cottage in Deep River

4.9 out of 5 average rating, 42 reviews

Country Cottage in Private Garden Setting

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

Total rentals
40 properties
Nightly prices starting at
$108 SGD before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Destinations to explore