A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.

Holiday Homes in Madison

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Madison holiday homes

A modern kitchen with a granite island, stainless steel appliances, and a bar area with bar stools.

1. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (3 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is NZ$1,062
includes taxes & fees
1 Dec - 2 Dec
Beachside Bliss w/ Game Room, Gym & Golf Green
A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

2. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.4 out of 10, Exceptional, (93 reviews)
"This is a great location, walking distance to the green and other sites. It also worked well for our girls trip of 4 women."
United States
Liz H.
The price is NZ$1,053
includes taxes & fees
2 Nov - 3 Nov
Historic New England home ,Reunions Beach pass
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

3. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is NZ$953
includes taxes & fees
3 Nov - 4 Nov
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A living room with a dark grey sofa, a wooden coffee table with a vase of white flowers, a patterned rug, and a ceiling fan.

4. Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (12 reviews)
"Property was clean and had all amenities we needed. Easy check in and check out"
United States
Sarah S.
The price is NZ$279
includes taxes & fees
8 Nov - 9 Nov
Cozy East Haven Home • Near Beach & Yale
A modern living room with a gray sofa, a dining table with white chairs, a small coffee table, and a potted plant.

5. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
8.0 out of 10, Very good, (6 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is NZ$350
includes taxes & fees
2 Nov - 3 Nov
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

6. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is NZ$518
includes taxes & fees
12 Nov - 13 Nov
Once the old Schools house now a newly furnished Apartment
A modern kitchen with a central island, bar stools, and pendant lighting.

7. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
10.0 out of 10, Exceptional, (35 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is NZ$1,992
includes taxes & fees
2 Nov - 3 Nov
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A cozy living room with a sofa, a coffee table, and a dining area with chairs.

8. NEW private studio 1.1 miles to beach in East Lyme

NEW private studio 1.1 miles to beach in East Lyme
East Lyme
The price is NZ$256
includes taxes & fees
4 Nov - 5 Nov
NEW private studio 1.1 miles to beach in East Lyme
A modern living room with a leather sofa, a dining table with chairs, a kitchen area with white cabinets, and a chandelier.

9. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
The price is NZ$771
includes taxes & fees
2 Nov - 3 Nov
#29 - Modern 5 Bedroom/2 Bath
A spacious living room with a grey sectional sofa, a small ottoman, and a large window with a view.

10. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.8 out of 10, Exceptional, (16 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is NZ$485
includes taxes & fees
2 Nov - 3 Nov
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
A wooden deck with a table and chairs, overlooking a river and trees.

11. Steps to Beach • Hot Tub • Game Room • Water Views

Steps to Beach • Hot Tub • Game Room • Water Views
Branford
The price is NZ$2,154
includes taxes & fees
8 Nov - 9 Nov
Steps to Beach • Hot Tub • Game Room • Water Views
A covered patio with outdoor furniture, a door, and a view of a residential area.

12. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is NZ$403
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A room with a patterned rug, a door leading to a kitchen, and a window with blinds.

13. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Gilbert is an amazing host! I highly recommend staying here if you are visiting Middletown."
United States
Audrey F.
The price is NZ$429
includes taxes & fees
3 Nov - 4 Nov
Family Stays: Middletown, CT
A small, single-story house with a gabled roof, a front door, and a number "401" on the door.

14. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is NZ$745
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

15. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (51 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is NZ$422
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

16. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is NZ$888
includes taxes & fees
8 Nov - 9 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

17. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is NZ$616
includes taxes & fees
2 Nov - 3 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A patio area with wicker chairs and a table, surrounded by gravel and plants.

18. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is NZ$493
includes taxes & fees
4 Nov - 5 Nov
American Beech in Greenport - Petite King Room 7
A living room with a staircase, a sofa, a coffee table, and a TV.

19. Loft •Pool • Gym • Free Parking • Near Yale

Loft •Pool • Gym • Free Parking • Near Yale
Orange
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. Host was accommodating and quick to respond when we encountered issues."
United States
Ali B.
The price is NZ$421
includes taxes & fees
2 Nov - 3 Nov
Loft •Pool • Gym • Free Parking • Near Yale
A modern kitchen with a stainless steel refrigerator, wooden beams, a dining area with a table and chairs, and a large window with blinds.

20. Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is NZ$822
includes taxes & fees
2 Nov - 3 Nov
Coastal Landing Stay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Madison Hotel Reviews

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"The cabin was exceptionally clean. It had everything we needed for the weekend. The staff were very responsive to questions and requests. Would definitely go back again"
Maria 2-night trip
Posted 1 hour ago
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Find out more about Madison

Madison Holiday Homes information

Number of reviews
486
Accommodation
545 Holiday Homes
Lowest Price
NZ$279
Highest Price
NZ$2,154