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)

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”.

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!

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!

Guest favorite

Apartment in Guilford

4.98 out of 5 average rating, 249 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.

Guest favorite

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.

Guest favorite

Home in Milford

4.98 out of 5 average rating, 153 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!

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.

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.

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.

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.

Guest favorite

Apartment in Deep River

4.82 out of 5 average rating, 171 reviews

Loft apartment, deck and great water view

Great location, walk to town & only steps to the Connecticut River. Great for train aficionados- you can watch and photograph the famous Essex steam train in action.This historic factory built in 1874 has manufactured sails, metal objects and lastly Lace. Enjoy your private comfortable apartment with river views and deck.

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

Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 104 reviews

Walk to the beach at Black Point, Niantic, Ct

Guest favorite

Tiny home in East Lyme

5.0 out of 5 average rating, 101 reviews

Luxury Tiny Home Near Rocky Neck

Guest favorite

Guesthouse in Mystic

4.99 out of 5 average rating, 538 reviews

Gorgeous Waterfront Getaway

Guest favorite

Home in Branford

4.98 out of 5 average rating, 124 reviews

Shoreline Treasure in Lanphiers Cove

Guest favorite

Home in Milford

4.89 out of 5 average rating, 124 reviews

The Beach House!

Guest favorite

Guesthouse in Madison

4.92 out of 5 average rating, 13 reviews

In-law apartment with Private entrance

Guest favorite

Home in Madison

5.0 out of 5 average rating, 18 reviews

Writer's Retreat & Explorer's Adventure!

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Madison house rentals

Guest favorite

Home in Lyme

4.97 out of 5 average rating, 187 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

Guest favorite

Home in Manchester

4.94 out of 5 average rating, 174 reviews

Paradise On The Hill Luxury Apartment.

Guest favorite

Home in Stony Brook

4.94 out of 5 average rating, 478 reviews

Spacious Studio Apartment- near SBU

Guest favorite

Home in Preston

4.96 out of 5 average rating, 598 reviews

Entire House Magical Waterfront Getaway

Guest favorite

Home in Old Lyme

4.94 out of 5 average rating, 257 reviews

Modern Luxurious CT Country Home

Guest favorite

Home in New Haven

5.0 out of 5 average rating, 169 reviews

Historic New Haven Home

Guest favorite

Home in Cheshire

5.0 out of 5 average rating, 117 reviews

Pool House

Guest favorite

Home in New Haven

4.99 out of 5 average rating, 184 reviews

Q River House - 2 bdrm, minutes from Yale/Downtown

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Beach house rentals in Madison

Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 163 reviews

Beachfront Paradise

Guest favorite

Home in Greenport

4.92 out of 5 average rating, 422 reviews

Blue Bay Dream - Apt #1

Guest favorite

Home in Centerport

4.96 out of 5 average rating, 112 reviews

The Harbor House: Beachfront Home 1 hour from NYC

Guest favorite

Home in Old Lyme

4.96 out of 5 average rating, 120 reviews

Cozy Beach Cottage with short walk to the beach

Guest favorite

Home in Shelter Island

4.97 out of 5 average rating, 193 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Guest favorite

Home in Montauk

4.91 out of 5 average rating, 416 reviews

DITCH PLAINS SURF HOUSE

Guest favorite

Home in Milford

4.99 out of 5 average rating, 229 reviews

The Daydreamer -Walk to Walnut Beach, Pet Friendly

Guest favorite

Home in Branford

4.88 out of 5 average rating, 177 reviews

Gorgeous 4BR Beach House - 250 ft to private beach

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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

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Madison?
Yes! Work meets play with ease at over 50 vacation rentals in Madison featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Madison?
Four-legged friends are welcome in Madison. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Madison?
Experience the best of Madison with our apartment rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Madison house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Madison, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Madison have a gym?
Absolutely! We offer over 10 house rentals with a gym in Madison. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Madison have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Madison. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Madison have self check-in?
Absolutely! We offer over 20 house rentals with self check-in in Madison. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Madison?
Madison has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Madison vacation rentals

Top-rated vacation rentals in Madison

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Madison vacation rentals

Stay near Madison's top sights

Other great vacation rentals in Madison

Bungalow in Milford

Home in East Lyme

Tiny home in East Lyme

Guesthouse in Mystic

Home in Branford

Home in Milford

Guesthouse in Madison

Home in Madison

Madison house rentals

Home in Lyme

Home in Manchester

Home in Stony Brook

Home in Preston

Home in Old Lyme

Home in New Haven

Home in Cheshire

Home in New Haven

Beach house rentals in Madison

Home in East Lyme

Home in Greenport

Home in Centerport

Home in Old Lyme

Home in Shelter Island

Home in Montauk

Home in Milford

Home in Branford

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

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Madison?

Are there pet-friendly vacation rentals in Madison?

How much does it cost to stay in apartment rentals in Madison?

Are there Madison house rentals on Airbnb with pools?

Do house rentals in Madison have a gym?

Do house rentals in Madison have a bbq area?

Do house rentals in Madison have self check-in?

Are there family-friendly house rentals in Madison?

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