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.
Cottage in Guilford
4.96 out of 5 average rating, 157 reviewsLuxury 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
Cottage in Guilford
4.93 out of 5 average rating, 241 reviewsCharm + 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
Apartment in Milford
4.97 out of 5 average rating, 505 reviewsWater 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Madison vacation rentals
Madison beach vacation rentals
Cottage in Riverhead
4.98 out of 5 average rating, 126 reviewsSavor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Mar 26 – Apr 2
Home in East Haven
4.88 out of 5 average rating, 195 reviewsBeach Cottage by the Sea
Oct 8 – 15
Bungalow in Milford
4.99 out of 5 average rating, 208 reviewsSpring Sale! Beach Bungalow |Walk2Beach |Pet | Pkg
Aug 11 – 18
Guesthouse in Mystic
4.99 out of 5 average rating, 535 reviewsGorgeous Waterfront Getaway
Oct 5 – 10
Guest suite in Cutchogue
4.88 out of 5 average rating, 582 reviewsWalk to Vineyards, Beaches, Farms & Town
Aug 27 – Sep 3
Cottage in Waterford
4.99 out of 5 average rating, 103 reviewsClassic CT Cottage w/ Trail by Harkness Park/Ocean
Apr 12 – 19
Guest suite in Wading River
4.9 out of 5 average rating, 227 reviewsBeachy En Suite /Gateway to The North Fork
Apr 12 – 19
Home in Branford
4.98 out of 5 average rating, 124 reviewsShoreline Treasure in Lanphiers Cove
Apr 24 – May 1
Cottage in Branford
4.86 out of 5 average rating, 195 reviewsCozy Home In Short Beach Community
Nov 4 – 11
Apartment in Northport
4.92 out of 5 average rating, 126 reviewsHarbor Studio - Across from historic Northport doc
Oct 13 – 20
Townhouse in Westbrook
4.92 out of 5 average rating, 184 reviewsWake up with views of the ocean
Sep 10 – 17
Apartment in West Haven
4.9 out of 5 average rating, 412 reviews! ! ! entire apartment close to the beach ! !
Mar 2 – 9
Madison house rentals
Home in Cheshire
5.0 out of 5 average rating, 116 reviewsPool House
Oct 31 – Nov 7
Home in Preston
4.96 out of 5 average rating, 595 reviewsEntire House Magical Waterfront Getaway
Dec 29 – Jan 5
Home in Lyme
4.97 out of 5 average rating, 185 reviews“The Answer” Tidal River-Kayaks Fire pit Fireplace
Sep 28 – Oct 5
Home in Stony Brook
4.94 out of 5 average rating, 478 reviewsSpacious Studio Apartment- near SBU
Mar 16 – 23
Home in Old Lyme
4.94 out of 5 average rating, 256 reviewsModern Luxurious CT Country Home
Oct 2 – 9
Home in New Haven
4.99 out of 5 average rating, 179 reviewsQ River House - 2 bdrm, minutes from Yale/Downtown
Nov 5 – 12
Home in Manchester
4.94 out of 5 average rating, 172 reviewsParadise On The Hill Luxury Apartment.
Dec 4 – 11
Home in Centerport
4.95 out of 5 average rating, 111 reviewsThe Harbor House: Beachfront Home 1 hour from NYC
Jul 24 – 31
Home in Lyme
4.91 out of 5 average rating, 288 reviewsStunning, peaceful and private home
Dec 27 – Jan 3
Home in Bristol
4.92 out of 5 average rating, 102 reviewsCozy Family Home - Kid & Pet Friendly
Dec 31 – Jan 7
Home in Wilton
4.94 out of 5 average rating, 158 reviewsMid Century Modern Cottage
Jan 6 – 13
Home in Danbury
4.99 out of 5 average rating, 335 reviewsBEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!
Nov 15 – 22
Beach house rentals in Madison
Home in Greenport
4.94 out of 5 average rating, 136 reviewsBlue Bay Dream - Apt #2
Feb 11 – 18
Home in Milford
4.99 out of 5 average rating, 223 reviewsThe Daydreamer -Walk to Walnut Beach, Pet Friendly
Mar 19 – 26
Home in Port Jefferson
4.95 out of 5 average rating, 133 reviewsThe Hidden Retreat ~ Family friendly Walk to Beach
Apr 8 – 15
Home in Montauk
4.91 out of 5 average rating, 412 reviewsDITCH PLAINS SURF HOUSE
Nov 1 – 8
Home in New Haven
4.97 out of 5 average rating, 117 reviewsLI Sound waterview! Take Wedding pics, Yale&Beach
Dec 3 – 10
Home in Shelter Island
4.97 out of 5 average rating, 189 reviewsHuge Island Getaway Pool HotTub Walk To Beach
Jan 27 – Feb 3
Home in Old Saybrook
4.96 out of 5 average rating, 103 reviewsYear Round Beach House in Old Saybrook, CT.- Pets
Apr 2 – 9
Home in Old Lyme
4.96 out of 5 average rating, 118 reviewsCozy Beach Cottage with short walk to the beach
Oct 12 – 19
Home in Milford
4.89 out of 5 average rating, 195 reviewsRenovated House Steps Away From The Ocean
Feb 1 – 8
Home in Stonington
4.95 out of 5 average rating, 166 reviewsRomantic Seaside Cottage in Mystic
Oct 19 – 26
Home in Rocky Point
4.91 out of 5 average rating, 175 reviewsThe Katalpa House -by the beach
Jan 7 – 14
Home in Madison
4.86 out of 5 average rating, 14 reviewsHistoric Beachside Glamour
Apr 5 – 12
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.
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