Vacation rentals in Madison

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Top-rated vacation 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.

Jan. 13 – 20

$258 CAD per night

Guest favourite

Guest suite in Wallingford

5.0 out of 5 average rating, 496 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.

Feb. 17 – 24

$136 CAD 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!

Sep. 17 – 24

$239 CAD 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.

Feb. 2 – 9

$639 CAD per night

Guest favourite

Tiny homes 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.

Oct. 4 – 11

$277 CAD per night

Guest favourite

Guesthouse in Madison

4.92 out of 5 average rating, 12 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!

Sep. 17 – 24

$216 CAD per night

Guest favourite

Home in Madison

5.0 out of 5 average rating, 9 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

Beautiful 4-Bedroom Residential Home in Madison, Connecticut - Contemporary Scandinavian Interior Design - Close to Local/State Beaches (~10 Minute Drive) - Close to Local Parks and Hiking Areas (~3 Minute Drive) - Welcoming Open Floorplan - Quality Furnishings and Finishes - Up-to-Date/Modern Features/Clean and Comfortable - Wonderful Garden and Grass Lawn - Private (House Sits on 2-Acre Parcel) - Enclosed Outdoor Shower - Surrounded by Natural Beauty of the Countryside

Aug. 26 – Sep. 2

$636 CAD per night

Guest favourite

Home in Madison

5.0 out of 5 average rating, 17 reviews

Newly Renovated Beach Cottage!

Take your vacation at this newly renovated adorable cottage in a great family community, and a 4 min walk to private beach! The cottage has a brand new kitchen and bath. 3 bedrooms and an additional breezeway space perfect for reading or an additional private sleeping space. The home has an outdoor patio, and outdoor shower. Spend the day at the private association beach. Please note **This close knit, family community has a strict, no large gathering rule **

May 17 – 24

$657 CAD 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.

Mar. 25 – Apr. 1

$284 CAD 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.

Sep. 30 – Oct. 7

$249 CAD 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.

Mar. 22 – 29

$224 CAD per night

Guest favourite

Home in Madison

5.0 out of 5 average rating, 18 reviews

Writer's Retreat & Explorer's Adventure!

South of Rte. 1 Madison! Welcome to The River House. Experience a combination of spectacular marsh and water views along with designer inspired finishes. Kayak out to the Long Island Sound or enjoy the sun rising over the marsh among the Great Blue Herons.

Sep. 1 – 8

$483 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Madison vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Madison's top sights

Lenny & Joe's Fish Tale23 locals recommend

Jacobs Beach17 locals recommend

Clam Castle7 locals recommend

The Place Restaurant31 locals recommend

Madison Beach Hotel, Curio Collection by Hilton13 locals recommend

Shoreline Diner & Vegetarian Enclave12 locals recommend

Other great vacation rentals in Madison

Guest favourite

Cottage in Clinton

4.98 out of 5 average rating, 91 reviews

Guest House at the Marina

Dec. 4 – 11

$269 CAD per night

Guest favourite

Barn in Guilford

4.95 out of 5 average rating, 76 reviews

Pristine Carriage House Apartment Downtown

Sep. 27 – Oct. 4

$284 CAD per night

Guest favourite

Home in Haddam

5.0 out of 5 average rating, 73 reviews

Cozy Comforts!

Dec. 6 – 13

$202 CAD per night

Guest favourite

Apartment in Guilford

4.96 out of 5 average rating, 25 reviews

Charming loft in Guilford

Sep. 12 – 19

$249 CAD per night

Guest favourite

Loft in Killingworth

4.89 out of 5 average rating, 18 reviews

A Peaceful Perch

Jun. 11 – 18

$217 CAD per night

Guest favourite

Guest suite in Guilford

4.93 out of 5 average rating, 75 reviews

Old Salt Oasis: serene, spacious, pets welcome!

May 28 – Jun. 4

$335 CAD per night

Guest favourite

Loft in Westbrook

5.0 out of 5 average rating, 59 reviews

Lovely one bedroom studio with on-site parking.

Mar. 16 – 23

$230 CAD per night

Guest favourite

Home in Madison

4.91 out of 5 average rating, 34 reviews

Coastal getaway with water views in every room

Aug. 7 – 14

$1,335 CAD per night

Show all

Quick stats about vacation rentals in Madison

Total rentals	130 properties
Rentals with dedicated workspaces	50 properties have a dedicated workspace
Rentals with a pool	10 properties have a pool
Pet-friendly rentals	40 properties allow pets
Family-friendly rentals	80 properties are a good fit for families
Total number of reviews	3.8K reviews

Vacation rentals in Madison

Top-rated vacation rentals in Madison

Apartment in Guilford

Guest suite in Wallingford

Apartment in Guilford

Guesthouse in Madison

Tiny homes in Guilford

Guesthouse in Madison

Home in Madison

Home in Madison

Guesthouse in Madison

Home in Guilford

Apartment in Madison

Home in Madison

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Madison vacation rentals

Stay near Madison's top sights

Other great vacation rentals in Madison

Cottage in Clinton

Barn in Guilford

Home in Haddam

Apartment in Guilford

Loft in Killingworth

Guest suite in Guilford

Loft in Westbrook

Home in Madison

Quick stats about vacation rentals in Madison

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore