Holiday houses in Madison

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Top-rated holiday rentals in Madison

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Guest favourite

Apartment in Guilford

4.98 out of 5 average rating, 248 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

13–20 Nov

$324 NZD per night

Superhost

Home in Madison

4.79 out of 5 average rating, 14 reviews

Charming beach cottage in Madison, CT

Enjoy your coffee on the front porch, then spend the day at the private association beach, just a short walk away! A queen sized bed for 2 and two twin beds for 4 other children or adults. The bathroom has two separate showers, so that more than one person can get ready at once. Peloton bike and free standing weights (must have your own Peloton membership). Restaurants and brewery nearby for IPA and cider lovers. Quaint center of town has cream shop, book store, movie theatre and boutiques.

26 Feb – 5 Mar

$792 NZD per night

Guest favourite

Guest suite in Wallingford

5.0 out of 5 average rating, 499 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.

9–16 Feb

$167 NZD per night

Guest favourite

Apartment in Guilford

4.9 out of 5 average rating, 20 reviews

Cozy Private Lake Q Retreat

Escape to a charming lakeside haven! Our cozy 1-bed, 1-bath retreat is a tranquil getaway. Nestled by the water, it's perfect for a romantic escape or a solo recharge. Enjoy stunning lake views, a comfy bedroom, and a serene bathroom. Unwind on the private deck, take a dip in the crystal-clear waters, or explore nearby nature trails. A lofted office space with l-shaped desk and computer monitor with connection hub invites both creativity and productivity. Your lakeside escape awaits!

2–9 Dec

$293 NZD per night

Guest favourite

Guesthouse in Madison

4.97 out of 5 average rating, 67 reviews

Beachy & Bright Carriage House/5 min walk to Beach

Just 2 hrs from Boston/NYC, get away from it all w/this one a one of a kind, beautiful & spacious property. If you’re looking for a romantic weekend, girls getaway or a kid friendly space, you have found the perfect spot! Beach is 5 min walk, backyard is a kids paradise, 5 min drive to town. Antique shops, wineries, seafood restaurants all within 10 mins. Sit on private deck sipping coffee or wine and watch the sun rise or set. Hiking/biking/walking trails right out your front door.

4–11 Sep

$559 NZD per night

Guest favourite

Tiny home in Guilford

4.94 out of 5 average rating, 202 reviews

Stay in a Tiny House on a Small Sustainable Farm

Come stay in a tiny house on our sustainable farm! Tucked behind an unassuming neighborhood, feel your cares drop away as you drive down the long gravel driveway and our bucolic 8 acres open in front of you. We have goats, ducks and chickens. Hike, swim, kayak, play with goats, have a picnic or just plain relax. There are so many possibilities. The tiny house has AC/heat, wifi, full kitchen, full bath and a queen sized bed in the loft. Get away from it all here at Waystone Farm.

21–28 Aug

$340 NZD per night

Guest favourite

Guesthouse in Madison

4.92 out of 5 average rating, 13 reviews

In-law apartment with Private entrance

Welcome to our charming in-law apartment, the perfect retreat for your mini getaway. Nestled in a central location, our cozy space offers easy access to all that the area has to offer. Take a stroll to the beach, enjoy a round of golf, stock up on supplies at the nearby grocery store, and savor a delicious meal at local restaurants. Whether you're here for work or leisure, our in-law apartment provides a comfortable and convenient base for your stay. We can't wait to welcome you!

16–23 Nov

$259 NZD per night

Guest favourite

Guesthouse in Madison

5.0 out of 5 average rating, 58 reviews

The Barn by the Sound

Spend a weekend in The Barn: a modern designed free-standing building with guest studio apartment above, designed to look like a barn; the studio has views at tree level of a quiet, old neighborhood; one block from Long Island Sound; on a section of the historic old Boston Post Road. There is lots of natural light coming from a large window with a lovely view of a privet hedge on our property overlooking a park like property across the street.

16–23 Aug

$468 NZD per night

Guest favourite

Cottage in Clinton

4.98 out of 5 average rating, 92 reviews

Guest House at the Marina

A beautiful, modern one bedroom apartment on the second floor with a gorgeous view of the Indian River and tidal marsh. It is 600 sq feet, completely renovated, with a queen size bed, a well-appointed kitchen & bathroom. Walking distance to the Clinton train station. Stays in-season include use of 2 kayaks or SUPs per day (2 hours) provided by Indian River Kayak and Marina from Memorial Day to Labor Day.

6–13 Dec

$330 NZD per night

Guest favourite

Home in Guilford

4.95 out of 5 average rating, 19 reviews

Tiny home one block from the town green.

This special place is close to everything, The town green is one street over with local shops and restaurants. Walking distance to the train station, town marina, and the Guilford beach. It's a small home suitable for 2 people at the most. The bathroom is very small with a very small sink but a full size shower. AC/heat, wifi, full kitchen, shower, full size bed in a quiet private setting.

1–8 Oct

$306 NZD per night

Superhost

Home in Westbrook

4.86 out of 5 average rating, 134 reviews

Family-Friendly Cottage by The Shore

Whether you’re simply traveling to the area or planning your next vacation, you’ve found the right place. Leave your worries behind and come enjoy our freshly updated home by the shore. With a clean, comfortable and convenient spot to stay you are free to explore & relax.

13–20 Sep

$397 NZD per night

Guest favourite

Apartment in Madison

4.83 out of 5 average rating, 72 reviews

Beautifully Furnished Apartment

Is 5 minute walk to beach or town. Fully furnished and decorated with contemporary art. Features one bedroom with queen sized bed, spacious living room and small room with queen airmatress. Includes AC, parking, a TV with a fire stick for streaming, and patio with grill.

10–17 Feb

$276 NZD per night