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

Holiday Homes in Madison

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Madison holiday homes

A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

1. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is NZ$821
includes taxes & fees
20 Sept - 21 Sept
Adorable Cottage, 5 min walk to water & town
A glass-enclosed patio with a wooden table and wicker chairs, surrounded by glass doors and windows offering views of a wooded area.

2. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
The price is NZ$1,308
includes taxes & fees
28 Sept - 29 Sept
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is NZ$1,463
includes taxes & fees
18 Oct - 19 Oct
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.

4. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.2 out of 10, Wonderful, (90 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$1,121
includes taxes & fees
22 Sept - 23 Sept
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.

5. 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
29 Sept - 30 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
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, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is NZ$501
includes taxes & fees
28 Sept - 29 Sept
Once the old Schools house now a newly furnished Apartment
A spacious room with a large dining table and chairs, a sofa, and large windows offering a view of the sea and buildings.

7. Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Old Saybrook
9.8 out of 10, Exceptional, (41 reviews)
"Enjoyed our stay"
United States
Nicole L.
The price is NZ$1,649
includes taxes & fees
24 Sept - 25 Sept
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
A dining area with a table, chairs, a refrigerator, and wall-mounted lights.

8. Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
Fair Haven
5.6 out of 10, (4 reviews)
"Blankets where itchy and smelled dirty small room when whole house was listed"
United States
Isabella R.
The price is NZ$221
includes taxes & fees
18 Sept - 19 Sept
Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
A stone pier leading to a beach with houses in the background.

9. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is NZ$468
includes taxes & fees
29 Sept - 30 Sept
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

10. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is NZ$503
includes taxes & fees
22 Sept - 23 Sept
Newly Remodeled 1-BR Close to Everything yet Very Private
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

11. 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$554
includes taxes & fees
13 Oct - 14 Oct
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

12. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 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$397
includes taxes & fees
23 Sept - 24 Sept
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

13. #24 Serenity A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is NZ$589
includes taxes & fees
20 Sept - 21 Sept
#24 Serenity A Lakefront Cottage Retreat
A living room with a floral-patterned armchair, a dining table with chairs, a chandelier, and a wooden floor.

14. Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven

Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven
Foxon
10.0 out of 10, Exceptional, (1 review)
"Place looks way better in person, cozy and quiet. Loved the backyard and deck also plenty of fast food restaurants and Walmart near by."
United States
Fateema M.
Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven
A bedroom with a bed, a desk, and a chair. There are two windows with blinds, a lamp, and a rug on the floor.

15. Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
Newhallville
The price is NZ$692
includes taxes & fees
20 Sept - 21 Sept
Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to 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.

16. Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is NZ$847
includes taxes & fees
28 Sept - 29 Sept
Coastal Landing Stay
A dining area with a wooden table and white chairs, a potted plant, and a painting on the wall.

17. The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (7 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is NZ$771
includes taxes & fees
30 Sept - 1 Oct
The Bay Cottage · Rocky Neck Park, Beach & Niantic
A room with a large window overlooking a coastal view, a beige sofa, and a small table with books and a vase.

18. Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (13 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is NZ$893
includes taxes & fees
27 Sept - 28 Sept
Clear LI Sound waterview, Wedding pics, Yale&Beach
A modern kitchen with a central island, bar stools, and pendant lighting.

19. 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, (31 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$1,786
includes taxes & fees
21 Sept - 22 Sept
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A wooden pathway leading to a beach with scattered rocks and greenery.

20. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 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$729
includes taxes & fees
27 Sept - 28 Sept
Beach Block Hideaway
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

Zey Hotel

Zey Hotel

10/10 Excellent
"Great time, great stay, great staff! Will definitely be coming back!"
Amanda 2-night trip
Posted 12 hours ago
Zey Hotel

Find out more about Madison

Madison Holiday Homes information

Number of reviews
426
Accommodation
545 Holiday Homes
Lowest Price
NZ$221
Highest Price
NZ$1,786