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.

Guest favourite

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)

11–18 Feb

£307 per night
Guest favourite

Barn in Madison

4.95 out of 5 average rating, 40 reviews

Cozy 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

£220 per night
Guest favourite

Guest suite in Wallingford

5.0 out of 5 average rating, 495 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.

18–25 Jan

£75 per night

Popular amenities for Madison holiday 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

Other great holiday rentals in Madison

Superhost

Guest house in Guilford

4.84 out of 5 average rating, 38 reviews

Charming Bungalow walk to beach and town

17–24 Nov

£99 per night
Superhost

Home in Madison

4.86 out of 5 average rating, 14 reviews

Historic Beachside Glamour

5–12 Apr

£548 per night
Guest favourite

Home in Madison

4.91 out of 5 average rating, 11 reviews

Fun and Relaxing Madison Game Room Retreat

23–30 Apr

£380 per night
Guest favourite

Loft in Westbrook

5.0 out of 5 average rating, 58 reviews

Lovely one bedroom studio with on-site parking.

7–14 Sept

£133 per night
Guest favourite

Home in Haddam

5.0 out of 5 average rating, 69 reviews

Cozy Comforts!

29 Aug – 5 Sept

£127 per night
Guest favourite

Home in Madison

4.91 out of 5 average rating, 34 reviews

Coastal getaway with water views in every room

10–17 May

£512 per night
Guest favourite

Holiday home in Guilford

4.98 out of 5 average rating, 59 reviews

Spacious Oceanfront Getaway with Spectacular Views

3–10 Feb

£538 per night
Guest favourite

Cottage in Guilford

4.96 out of 5 average rating, 70 reviews

Direct Shoreline Long Island Sound Waterfront

23–30 Jun

£613 per night
Guest favourite

Home in Madison

5.0 out of 5 average rating, 33 reviews

Spacious Newly Furnished 4 BR Near Beach and Town

1–8 Nov

£588 per night
Guest favourite

Guest house in Madison

4.95 out of 5 average rating, 56 reviews

The Rising Tide Cottage

7–14 Aug

£291 per night
Guest favourite

Home in Guilford

5.0 out of 5 average rating, 6 reviews

Coast and Country Private Estate

23–30 Dec

£536 per night
Superhost

Guest house in Branford

4.79 out of 5 average rating, 47 reviews

Studio on the shore - Short Beach - Water Views

24 Sept – 1 Oct

£108 per night

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

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. New Haven County
  5. Madison