Madison vacation rentals

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Top-rated vacation rentals in Madison

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 157 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Dec 30 – Jan 6

R8,948 ZAR per night

Guest favorite

Cottage in Guilford

4.93 out of 5 average rating, 244 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”.

Dec 23 – 30

R5,472 ZAR per night

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 508 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Sep 25 – Oct 2

R3,851 ZAR per night

Superhost

Home in East Haven

4.88 out of 5 average rating, 196 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!

Feb 28 – Mar 7

R2,975 ZAR per night

Guest favorite

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.

Nov 13 – 20

R3,100 ZAR per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 498 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 9 – 16

R1,673 ZAR per night

Guest favorite

Yurt in Guilford

4.9 out of 5 average rating, 100 reviews

Hartwoods Yurt

Enjoy a unique, private, wilderness getaway and unwind in a peaceful wooded environment in our 30’ diameter Yurt, which sleeps 4 in North Guilford, CT. This elevated cylindrical dwelling offers solitude and a large deck with comfortable chairs and forest views. Shaded and cool in the summer with air conditioning and fans available. This Yurt provides a wonderful respite from the hectic world. Perfect for nature lovers with a nearby brook and miles of trails for hiking and mountain biking.

Jun 14 – 21

R4,085 ZAR per night

Guest favorite

Home in Milford

4.98 out of 5 average rating, 152 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Nov 21 – 28

R6,682 ZAR per night

Guest favorite

Home in Clinton

4.97 out of 5 average rating, 173 reviews

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

Dec 16 – 23

R5,628 ZAR per night

Guest favorite

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.

Aug 21 – 28

R3,319 ZAR per night

Guest favorite

Apartment in East Haddam

4.9 out of 5 average rating, 105 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Mar 6 – 13

R1,969 ZAR per night

Guest favorite

Guesthouse in Guilford

4.99 out of 5 average rating, 453 reviews

Get Back to Nature at a Modern Wood Clad Getaway

SPRING BIRDS HAVE ARRIVED. Spring is here!!. Beautiful days and nights. Hike on the trails. Bike along the ocean. Cardinals, blue jays, bluebirds, gold finches and more. Great places to shop and eat or just relax in our cozy guest house. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Sep 16 – 23

R5,578 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Madison vacation rentals

Laptop-friendly workspace

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 favorite

Bungalow in Milford

4.99 out of 5 average rating, 214 reviews

Spring Sale! Beach Bungalow |WalktoBeach |Pet |Pkg

Oct 8 – 15

R4,580 ZAR per night

Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 104 reviews

Walk to the beach at Black Point, Niantic, Ct

Jan 26 – Feb 2

R2,910 ZAR per night

Guest favorite

Guest suite in Wading River

4.9 out of 5 average rating, 230 reviews

Beachy En Suite /Gateway to The North Fork

Apr 29 – May 6

R2,027 ZAR per night

Guest favorite

Tiny home in East Lyme

5.0 out of 5 average rating, 101 reviews

Luxury Tiny Home Near Rocky Neck

Aug 19 – 26

R7,370 ZAR per night

Guest favorite

Apartment in New Haven

4.93 out of 5 average rating, 148 reviews

Tranquil Apartment with Waterview, Walk to Beach!

May 2 – 9

R3,071 ZAR per night

Guest favorite

Home in Branford

4.98 out of 5 average rating, 124 reviews

Shoreline Treasure in Lanphiers Cove

Apr 28 – May 5

R5,120 ZAR per night

Guest favorite