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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Madison vacation rentals
Other great vacation rentals in Madison
Home in East Haven
4.88 out of 5 average rating, 196 reviewsBeach Cottage by the Sea
Jan 14 – 21
Guesthouse in Mystic
4.99 out of 5 average rating, 541 reviewsGorgeous Waterfront Getaway
Dec 9 – 14
Bungalow in Milford
4.99 out of 5 average rating, 215 reviewsSpring Sale! Beach Bungalow |WalktoBeach |Pet |Pkg
Sep 1 – 8
Guest suite in Wading River
4.9 out of 5 average rating, 230 reviewsBeachy En Suite /Gateway to The North Fork
Sep 3 – 10
Guest suite in Cutchogue
4.88 out of 5 average rating, 586 reviewsWalk to Vineyards, Beaches, Farms & Town
Oct 6 – 13
Tiny home in East Lyme
5.0 out of 5 average rating, 101 reviewsLuxury Tiny Home Near Rocky Neck
Aug 8 – 15
Home in Branford
4.98 out of 5 average rating, 125 reviewsShoreline Treasure in Lanphiers Cove
May 4 – 11
Home in Milford
4.89 out of 5 average rating, 124 reviewsThe Beach House!
May 17 – 24
Madison house rentals
Home in Lyme
4.97 out of 5 average rating, 189 reviews“The Answer” Tidal River-Kayaks Fire pit Fireplace
Jun 4 – 11
Home in Westbrook
4.86 out of 5 average rating, 134 reviewsFamily-Friendly Cottage by The Shore
Jul 22 – 29
Home in Stony Brook
4.94 out of 5 average rating, 478 reviewsSpacious Studio Apartment- near SBU
Feb 27 – Mar 6
Home in Manchester
4.94 out of 5 average rating, 175 reviewsParadise On The Hill Luxury Apartment.
Oct 8 – 15
Home in Preston
4.96 out of 5 average rating, 599 reviewsEntire House Magical Waterfront Getaway
Jan 5 – 12
Home in Cheshire
5.0 out of 5 average rating, 117 reviewsPool House
Nov 26 – Dec 3
Home in Old Lyme
4.94 out of 5 average rating, 257 reviewsModern Luxurious CT Country Home
Oct 14 – 21
Home in New Haven
4.99 out of 5 average rating, 187 reviewsQ River House - 2 bdrm, minutes from Yale/Downtown
Mar 15 – 22
Beach house rentals in Madison
Home in Milford
4.99 out of 5 average rating, 229 reviewsThe Daydreamer -Walk to Walnut Beach, Pet Friendly
Apr 5 – 12
Home in Greenport
4.98 out of 5 average rating, 165 reviewsAqua Vista
Jan 4 – 11
Home in Rocky Point
4.91 out of 5 average rating, 178 reviewsThe Katalpa House -by the beach
Feb 20 – 27
Home in East Lyme
4.96 out of 5 average rating, 164 reviewsBeachfront Paradise
Dec 12 – 19
Home in Montauk
4.91 out of 5 average rating, 418 reviewsDITCH PLAINS SURF HOUSE
Mar 12 – 19
Home in Old Lyme
4.96 out of 5 average rating, 124 reviewsCozy Beach Cottage with short walk to the beach
Mar 17 – 24
Home in New Haven
4.97 out of 5 average rating, 124 reviewsWaterviewsTakeWedding pics,CollegeTours Yale&Beach
Jun 2 – 9
Home in Port Jefferson
4.96 out of 5 average rating, 135 reviewsThe Hidden Retreat ~ Family friendly Walk to Beach
Jul 16 – 21
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 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 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.
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