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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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 £361
includes taxes & fees
30 Sept - 1 Oct
Adorable Cottage, 5 min walk to water & town
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

2. 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 £506
includes taxes & fees
27 Oct - 28 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.

3. 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 £484
includes taxes & fees
30 Sept - 1 Oct
Historic New England home ,Reunions Beach pass
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

4. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (14 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is £369
includes taxes & fees
1 Oct - 2 Oct
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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 £419
includes taxes & fees
30 Sept - 1 Oct
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A stone pier leading to a beach with houses in the background.

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (61 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 £207
includes taxes & fees
6 Oct - 7 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

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

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is £223
includes taxes & fees
4 Oct - 5 Oct
Once the old Schools house now a newly furnished Apartment
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

8. 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 £241
includes taxes & fees
13 Oct - 14 Oct
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

9. 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 £227
includes taxes & fees
6 Oct - 7 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
A modern kitchen with a central island, bar stools, and pendant lighting.

10. 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, (33 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 £783
includes taxes & fees
2 Oct - 3 Oct
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A hotel room with a bed, two bedside tables with lamps, a ceiling fan, a door, and a framed abstract artwork on the wall.

11. 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 £279
includes taxes & fees
30 Sept - 1 Oct
The Bay Cottage · Rocky Neck Park, Beach & Niantic
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 £348
includes taxes & fees
9 Oct - 10 Oct
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 £266
includes taxes & fees
12 Oct - 13 Oct
#24 Serenity A Lakefront Cottage Retreat
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

14. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is £242
includes taxes & fees
18 Oct - 19 Oct
The SandPiper
A dining area with a table, chairs, a refrigerator, and wall-mounted lights.

15. 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, (5 reviews)
The price is £99
includes taxes & fees
30 Sept - 1 Oct
Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
A modern living room with a sofa, a dining table, and a massage chair.

16. #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 £374
includes taxes & fees
7 Oct - 8 Oct
#29 - Modern 5 Bedroom/2 Bath
Veterans Park, near the house

17. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (31 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is £196
includes taxes & fees
27 Oct - 28 Oct
Family Stays: Middletown, CT
A wooden deck with a table and chairs, overlooking a river and trees.

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

Steps to Beach • Hot Tub • Game Room • Water Views
Branford
The price is £970
includes taxes & fees
4 Oct - 5 Oct
Steps to Beach • Hot Tub • Game Room • Water Views
A wooden pathway leading to a beach with scattered rocks and greenery.

19. 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 £395
includes taxes & fees
12 Oct - 13 Oct
Beach Block Hideaway
A room with a large window overlooking a coastal view, a beige sofa, and a small table with books and a vase.

20. 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 £445
includes taxes & fees
30 Sept - 1 Oct
Clear LI Sound waterview, Wedding pics, Yale&Beach
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

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"Great! Good coffee kiosk near lobby! Good cappuccino, etc."
John 4-night trip
Posted less than an hour ago
Omni New Haven Hotel at Yale

Find out more about Madison

Madison Holiday Homes information

Number of reviews
523
Accommodation
539 Holiday Homes
Lowest Price
£99
Highest Price
£970