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House vacation rentals in Madison

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Popular amenities for Madison house rentals

House rentals with a pool

Top guest favorite
A light-filled living area features a neutral-colored sofa alongside a blue couch, with decorative pillows adding subtle color. A wooden coffee table rests in front, and large windows with bamboo shades allow natural light to brighten the space.
Home in North Fork
4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

EricRating, 5 stars7 months ago
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.
Guest favorite
A light-filled dining area features a round wooden table surrounded by four white chairs. French doors open to a lush outdoor space, and the wood-beamed ceiling adds a rustic touch. The adjacent kitchen with white cabinetry is partially visible, enhancing the open feel.
Home in East Hampton
4.88 out of 5 average rating, 107 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

IanRating, 5 stars1 month ago
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.
Superhost
A modern home is showcased with a unique angular design, featuring a combination of wood and glass. The surrounding lawn is spacious and well-maintained, with natural landscaping, including grasses and a small tree, contributing to the serene outdoor setting.
Home in East Hampton
4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

BrittanyRating, 5 stars8 months ago
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 133 reviews

Pool House

EllenRating, 5 stars2 weeks ago
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.
Top guest favorite
The outdoor area features a large in-ground pool surrounded by a fence, with lounge chairs and shaded umbrellas. A spacious wooden deck is visible, along with seating and a small shed. The lush greenery of the backyard complements the serene setting.
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Guest favorite
A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars2 months ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Top guest favorite
A welcoming living area showcases a light grey sofa and two upholstered chairs flanking a coffee table. Natural light floods the space through large windows, highlighting a collection of framed artwork on the wall. A modern chandelier adds a stylish touch overhead.
Home in East Hampton
5 out of 5 average rating, 36 reviews

Stunning Central E. Hampton Home w/ gunite pool.

DonnaRating, 5 stars3 months ago
Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!
Guest favorite
Home in Montville
4.94 out of 5 average rating, 152 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

JaedyRating, 5 stars1 week ago
Great place and Great Host. Clean place and easy to find.

Weekly house rentals

Guest favorite
A black lounge chair is positioned beside large glass doors, offering views of Napeague Harbor. Natural light fills the space, highlighting the warm wooden floors and nearby outdoor seating. A shading sail is visible outside, along with a pop of red from an umbrella.
Home in Amagansett
4.93 out of 5 average rating, 14 reviews

Amagansett, Waterfront retreat

DanielleRating, 5 stars8 months ago
My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!
Guest favorite
A charming historic bungalow is presented with a shingle exterior and turquoise accents. The entrance is framed by flower boxes, and brick paving extends to the driveway. Lush greenery surrounds the property, while clear blue skies complement the inviting facade.
Home in North Fork
4.98 out of 5 average rating, 187 reviews

Nofo Bungalow-In The Heart of Greenport Village

JaclynRating, 5 stars2 weeks ago
We cannot get enough of this amazing North Fork bungalow! We have enjoyed staying here several times over the last 5 years and hope to be back again next year! The space is perfect for our family of 6! We enjoy making a fire pit out back, cooking dinner together in the kitchen, playing games at the dining room table and snuggling up together on the couch! Our 4 kids cannot get enough of the bedroom upstairs! They love reading, playing games and being altogether for a big sleepover! We love taking a break from our busy life to relax and enjoy walks to town for coffee and dinner, hiking on the beach, the wineries and taking a trip over to Shelter island to hike and explore! Thank you again for having us and for all of the memories we have made together in your beautiful house! We hope to see you again next year!
Guest favorite
Home in North Fork
4.97 out of 5 average rating, 254 reviews

The Greenport Bungalow

SaraRating, 5 stars1 month ago
This is an AMAZING Airbnb. High quality blankets, towels, ornamental details throughout the space. Comfortable beds. Beautiful ambient lighting. Large backyard with a fire pit. The neighborhood is quiet, beautiful houses, surrounded by water, with lovey little shores and nooks to walk to. My 4 year old had toys to play with and a little potty that all came with the home. I will DEFINITELY stay again. My family and I loved this place.
Top guest favorite
A blue bungalow exterior is shown, featuring a spacious deck with black railings and multiple glass doors. A picnic table is situated on the lawn, alongside a children's toy. Lush greenery surrounds the property, enhancing the setting.
Home in Montauk
5 out of 5 average rating, 20 reviews

Montauk beach house!

StephanieRating, 5 stars6 months ago
Lovely, well kept and comfortably furnished. This home has everything you need for a comfortable stay. Owner is helpful and very responsive. Highly recommened!
Guest favorite
A bright, open-concept living area features a large wooden dining table surrounded by textured chairs. Expansive windows invite natural light and showcase views of the surrounding greenery. A cozy seating area is arranged near a fireplace, with modern decor enhancing the space's aesthetic.
Home in Montauk
4.95 out of 5 average rating, 38 reviews

Lux Montauk Retreat:Pool,Water Views,Sunsets Deck

KathleenRating, 5 stars7 months ago
I cannot say enough amazing things about this house - our stay was absolutely sublime. The decor was immaculately curated, the house had all the supplies required to cook family meals, the sunset was to die for, and we had an absolute blast at the pool. Communicating with Dan and Tabitha was great, very professional and responsive. The home was incredibly clean - it was the nicest AirBnb I've ever stayed in BY FAR, already looking forward to booking again. THANK YOU!
Top guest favorite
The exterior of a charming two-story house is presented, featuring light siding and dark shutters. Window boxes adorned with blue flowers are visible. A small porch with a door leads into the home, accompanied by a stone pathway and neatly landscaped shrubs.
Home in Old Saybrook
4.97 out of 5 average rating, 121 reviews

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

SueRating, 5 stars1 week ago
Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.
Guest favorite
Home in Madison
4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

GretchenRating, 5 stars6 months ago
A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.
Guest favorite
A bright living area features a large flat-screen TV mounted on a white console. Two colorful armchairs and a brown leather couch surround a wooden coffee table, all set on a blue area rug. Light streams in through a window, enhancing the cozy atmosphere.
Home in East Hampton
4.92 out of 5 average rating, 93 reviews

Clean private home near Lake Pocotopaug!

CathyRating, 5 stars4 months ago
I highly recommend this property. It was perfect for our Christmas visit with family. The furniture and beds were very comfortable. We truly enjoyed our stay in East Hampton. We will be back!

Private house rentals

Guest favorite
The exterior of a single-story home is set among lush greenery, featuring a varied facade with shingle and clapboard elements. Symmetrical landscaping includes neatly trimmed shrubs and a spacious lawn. A pathway leads to the front door, framed by tall trees providing natural shade.
Home in Shelter Island
4.88 out of 5 average rating, 26 reviews

Peaceful and Private 3 bedroom home in the woods

Robert,Donald JrRating, 5 stars8 months ago
Maura was an excellent host and the home was perfect! We enjoyed the weekend very much and cannot thank Maura enough for her kindness, responsiveness, warm hearted spirit, and for opening up her home to us. Will always keep this spot in mind for future SI adventures!
Top guest favorite
The exterior of a charming farmhouse is shown, surrounded by a lush, green landscape. A gravel driveway leads to the entrance, while a wooden fence and two bicycles are visible in the foreground. The home features a blend of natural wood and modern elements against a clear blue sky.
Home in East Hampton
5 out of 5 average rating, 14 reviews

Restored farmhouse, walk to Carissa's, beach, town

IsabelRating, 5 stars7 months ago
We just spent an unforgettable weekend at J.P’s beautiful house, and we can't wait to be back! The house is absolutely beautiful, with impeccable taste and attention to detail. But what truly makes this property shine is its phenomenal location. Right in the middle of East Hampton and Amagansett and a 15 minute drive to Sag Harbor— couldn’t have asked for more. Also Carissa’s bakery is just a 6 minute walk. And, of course, no Hampton's experience is complete without a visit to Goldberg's for their classic lox and bagels - which is also a short walk away. The house itself is spacious, bright, and beautifully appointed, with everything you need to unwind and relax. Every room is nice and cozy and the kitchen is stunning with everything you need to cook with the amazing produce available at the so many farm stands around the area. (We loved Balsam and Amber Waves) J.P. was incredibly responsive and thoughtful, providing excellent recommendations and ensuring our stay was perfect.
Guest favorite
The exterior of the house features a multi-level deck and abundant autumn foliage in vibrant colors covering the ground. Two decorative benches are situated in the foreground, offering a tranquil spot to enjoy the surrounding nature.
Home in Chester
4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

TimRating, 5 stars6 months ago
We'd been looking forward to coming back to The Recycle House since we first stayed there in 2022. Safe to say it was just as we remembered it...great house, great location, wonderful community. Looking forwarded to returning.
Guest favorite
The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars3 weeks ago
It was wonderful stay and I’d go back anytime
Superhost
A two-story home features a welcoming front porch with steps leading up to it. A gravel driveway is visible, bordered by lush greenery and flowering bushes. Bicycles can be seen propped against the house, surrounded by a peaceful, natural setting.
Home in East Hampton
4.74 out of 5 average rating, 89 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

AntoineRating, 5 stars8 months ago
Mike is a great host with helpful recommendations and plenty of advice. The house is amazing. Well located, calm, clean and so convenient. The pool is huge and very deep. Everything is perfect. Felt like at home. We will be back
Guest favorite
A spacious outdoor area is visible, featuring a winding path that leads through a grassy landscape. Trees of varying heights frame the view, capturing seasonal colors with a backdrop of rolling hills under a clear blue sky.
Home in New Milford
4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

ConnieRating, 5 stars1 month ago
A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries
Guest favorite
The white estate is framed by bare trees, showcasing a combination of traditional architecture and natural surroundings. A serene lawn is visible in the foreground, with stone walls adding rustic charm. Soft lighting illuminates the porch, creating a welcoming atmosphere.
Home in East Haddam
5 out of 5 average rating, 25 reviews

Elegant Countryside Estate

AnjaliRating, 5 stars5 months ago
Spent a wonderful Thanksgiving weekend at Travis' place with my husband and two young daughters. The house is beautifully appointed and so cozy. We played games by the fire, watched a movie in the cozy tv room, and made and enjoyed lovely meals in the kitchen. The house is even more magical than it looks in the photos, and we certainly hope to be back.
Guest favorite
A modern kitchen features sleek black cabinetry and stainless steel appliances. A large island with bar seating is centered, adorned with a vase of fresh flowers. Natural light floods in through the windows, and a sliding glass door leads to the outdoor deck.
Home in Lyme
4.92 out of 5 average rating, 330 reviews

Stunning, peaceful and private home

KimRating, 5 stars2 weeks ago
The house was great and we were able to get Ubers to go to dinner. Beautiful house and stocked with everything you would need. We were on a girls weekend and had trouble with the locks but we just used the key. It could have just been us. We had a wonderful time and enjoyed the home.

Quick stats about house rentals in Madison

  • Total rentals

    60 properties

  • Total number of reviews

    1.9K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 properties include access to wifi

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