Madison vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Madison

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

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)

Feb 11 – 18

R6,340 ZAR per night
Guest favorite

Cottage in Guilford

4.93 out of 5 average rating, 241 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”.

Nov 27 – Dec 4

R5,484 ZAR per night
Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 505 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!

Aug 27 – Sep 3

R3,805 ZAR per night

Popular amenities for Madison vacation rentals

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
Cristy's Madison12 locals recommend

Madison beach vacation rentals

Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Mar 26 – Apr 2

R14,103 ZAR per night
Superhost

Home in East Haven

4.88 out of 5 average rating, 195 reviews

Beach Cottage by the Sea

Oct 8 – 15

R2,939 ZAR per night
Guest favorite

Bungalow in Milford

4.99 out of 5 average rating, 208 reviews

Spring Sale! Beach Bungalow |Walk2Beach |Pet | Pkg

Aug 11 – 18

R5,909 ZAR per night
Guest favorite

Guesthouse in Mystic

4.99 out of 5 average rating, 535 reviews

Gorgeous Waterfront Getaway

Oct 5 – 10

R3,416 ZAR per night
Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 582 reviews

Walk to Vineyards, Beaches, Farms & Town

Aug 27 – Sep 3

R3,069 ZAR per night
Guest favorite

Cottage in Waterford

4.99 out of 5 average rating, 103 reviews

Classic CT Cottage w/ Trail by Harkness Park/Ocean

Apr 12 – 19

R2,868 ZAR per night
Guest favorite

Guest suite in Wading River

4.9 out of 5 average rating, 227 reviews

Beachy En Suite /Gateway to The North Fork

Apr 12 – 19

R1,810 ZAR per night
Guest favorite

Home in Branford

4.98 out of 5 average rating, 124 reviews

Shoreline Treasure in Lanphiers Cove

Apr 24 – May 1

R4,996 ZAR per night
Superhost

Cottage in Branford

4.86 out of 5 average rating, 195 reviews

Cozy Home In Short Beach Community

Nov 4 – 11

R3,812 ZAR per night
Guest favorite

Apartment in Northport

4.92 out of 5 average rating, 126 reviews

Harbor Studio - Across from historic Northport doc

Oct 13 – 20

R2,415 ZAR per night
Guest favorite

Townhouse in Westbrook

4.92 out of 5 average rating, 184 reviews

Wake up with views of the ocean

Sep 10 – 17

R5,943 ZAR per night
Guest favorite

Apartment in West Haven

4.9 out of 5 average rating, 412 reviews

! ! ! entire apartment close to the beach ! !

Mar 2 – 9

R1,848 ZAR per night

Madison house rentals

Guest favorite

Home in Cheshire

5.0 out of 5 average rating, 116 reviews

Pool House

Oct 31 – Nov 7

R2,734 ZAR per night
Guest favorite

Home in Preston

4.96 out of 5 average rating, 595 reviews

Entire House Magical Waterfront Getaway

Dec 29 – Jan 5

R3,480 ZAR per night
Guest favorite

Home in Lyme

4.97 out of 5 average rating, 185 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

Sep 28 – Oct 5

R6,447 ZAR per night
Guest favorite

Home in Stony Brook

4.94 out of 5 average rating, 478 reviews

Spacious Studio Apartment- near SBU

Mar 16 – 23

R1,958 ZAR per night
Guest favorite

Home in Old Lyme

4.94 out of 5 average rating, 256 reviews

Modern Luxurious CT Country Home

Oct 2 – 9

R7,756 ZAR per night
Guest favorite

Home in New Haven

4.99 out of 5 average rating, 179 reviews

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

Nov 5 – 12

R3,408 ZAR per night
Guest favorite

Home in Manchester

4.94 out of 5 average rating, 172 reviews

Paradise On The Hill Luxury Apartment.

Dec 4 – 11

R1,871 ZAR per night
Guest favorite

Home in Centerport

4.95 out of 5 average rating, 111 reviews

The Harbor House: Beachfront Home 1 hour from NYC

Jul 24 – 31

R14,705 ZAR per night
Guest favorite

Home in Lyme

4.91 out of 5 average rating, 288 reviews

Stunning, peaceful and private home

Dec 27 – Jan 3

R6,591 ZAR per night
Guest favorite

Home in Bristol

4.92 out of 5 average rating, 102 reviews

Cozy Family Home - Kid & Pet Friendly

Dec 31 – Jan 7

R2,600 ZAR per night
Guest favorite

Home in Wilton

4.94 out of 5 average rating, 158 reviews

Mid Century Modern Cottage

Jan 6 – 13

R2,615 ZAR per night
Guest favorite

Home in Danbury

4.99 out of 5 average rating, 335 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Nov 15 – 22

R2,789 ZAR per night

Beach house rentals in Madison

Superhost

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Blue Bay Dream - Apt #2

Feb 11 – 18

R1,693 ZAR per night
Guest favorite

Home in Milford

4.99 out of 5 average rating, 223 reviews

The Daydreamer -Walk to Walnut Beach, Pet Friendly

Mar 19 – 26

R4,366 ZAR per night
Superhost

Home in Port Jefferson

4.95 out of 5 average rating, 133 reviews

The Hidden Retreat ~ Family friendly Walk to Beach

Apr 8 – 15

R8,439 ZAR per night
Guest favorite

Home in Montauk

4.91 out of 5 average rating, 412 reviews

DITCH PLAINS SURF HOUSE

Nov 1 – 8

R5,316 ZAR per night
Guest favorite

Home in New Haven

4.97 out of 5 average rating, 117 reviews

LI Sound waterview! Take Wedding pics, Yale&Beach

Dec 3 – 10

R6,696 ZAR per night
Guest favorite

Home in Shelter Island

4.97 out of 5 average rating, 189 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Jan 27 – Feb 3

R21,625 ZAR per night
Guest favorite

Home in Old Saybrook

4.96 out of 5 average rating, 103 reviews

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

Apr 2 – 9

R6,923 ZAR per night
Guest favorite

Home in Old Lyme

4.96 out of 5 average rating, 118 reviews

Cozy Beach Cottage with short walk to the beach

Oct 12 – 19

R5,324 ZAR per night
Superhost

Home in Milford

4.89 out of 5 average rating, 195 reviews

Renovated House Steps Away From The Ocean

Feb 1 – 8

R12,992 ZAR per night
Guest favorite

Home in Stonington

4.95 out of 5 average rating, 166 reviews

Romantic Seaside Cottage in Mystic

Oct 19 – 26

R4,838 ZAR per night
Guest favorite

Home in Rocky Point

4.91 out of 5 average rating, 175 reviews

The Katalpa House -by the beach

Jan 7 – 14

R2,999 ZAR per night
Superhost

Home in Madison

4.86 out of 5 average rating, 14 reviews

Historic Beachside Glamour

Apr 5 – 12

R10,900 ZAR per night

Quick stats about vacation rentals in Madison

Total rentals

120 properties

Rentals with dedicated workspaces

50 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

70 properties are a good fit for families

Total number of reviews

3.7K 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 30 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in cottage rentals in Madison?

    Experience the best of Madison with our cottage 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 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.

  • What are the most popular amenities for House Rentals in Madison?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with self check-in, over 40 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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  3. Connecticut
  4. New Haven County
  5. Madison