Holiday rentals in Madison
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Top-rated holiday rentals in Madison
Guests agree: these stays 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)
11–18 Feb
Barn in Madison
4.95 out of 5 average rating, 40 reviewsCozy Restored barn near beaches
Restored Barn 5 minutes from the beach and the lovely town of Madison, CT . Vaulted ceilings, stone fireplace, radiant heat floors, newly renovated bathroom and kitchenette. Downstairs is one large open room, with bathroom. Upstairs is a loft space with twin beds and TV/sitting room space. Great area for biking, kayaking and exploring the CT shoreline. Good for a couple, small families, girl friends weekend or alone time in the country. We would consider a well behaved furry companion too.
1–8 May
Guest suite in Wallingford
5.0 out of 5 average rating, 495 reviewsWintergreen 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.
18–25 Jan
Holiday rentals for every style
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Popular amenities for Madison holiday rentals
Other great holiday rentals in Madison
Guest house in Guilford
4.84 out of 5 average rating, 38 reviewsCharming Bungalow walk to beach and town
17–24 Nov
Home in Madison
4.86 out of 5 average rating, 14 reviewsHistoric Beachside Glamour
5–12 Apr
Home in Madison
4.91 out of 5 average rating, 11 reviewsFun and Relaxing Madison Game Room Retreat
23–30 Apr
Loft in Westbrook
5.0 out of 5 average rating, 58 reviewsLovely one bedroom studio with on-site parking.
7–14 Sept
Home in Haddam
5.0 out of 5 average rating, 69 reviewsCozy Comforts!
29 Aug – 5 Sept
Home in Madison
4.91 out of 5 average rating, 34 reviewsCoastal getaway with water views in every room
10–17 May
Holiday home in Guilford
4.98 out of 5 average rating, 59 reviewsSpacious Oceanfront Getaway with Spectacular Views
3–10 Feb
Cottage in Guilford
4.96 out of 5 average rating, 70 reviewsDirect Shoreline Long Island Sound Waterfront
23–30 Jun
Home in Madison
5.0 out of 5 average rating, 33 reviewsSpacious Newly Furnished 4 BR Near Beach and Town
1–8 Nov
Guest house in Madison
4.95 out of 5 average rating, 56 reviewsThe Rising Tide Cottage
7–14 Aug
Home in Guilford
5.0 out of 5 average rating, 6 reviewsCoast and Country Private Estate
23–30 Dec
Guest house in Branford
4.79 out of 5 average rating, 47 reviewsStudio on the shore - Short Beach - Water Views
24 Sept – 1 Oct
Quick stats about holiday 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 |
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