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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Madison vacation homes

An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

1. 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 ￥41,412
￥105,715 total
includes taxes & fees
Nov 3 - Nov 4
Beachside Bliss w/ Game Room, Gym & Golf Green
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

2. 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 ￥27,982
￥76,760 total
includes taxes & fees
Oct 15 - Oct 16
Adorable Cottage, 5 min walk to water & town
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 ￥47,400
￥101,594 total
includes taxes & fees
Oct 13 - Oct 14
Historic New England home ,Reunions Beach pass
A modern bathroom with a white toilet, wooden shelves, a wooden vanity, and a framed picture on the wall.

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, (15 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is ￥31,636
￥71,260 total
includes taxes & fees
Oct 12 - Oct 13
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 ￥45,504
￥87,011 total
includes taxes & fees
Nov 2 - Nov 3
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, (62 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 ￥17,795
￥43,061 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥18,644
￥46,089 total
includes taxes & fees
Oct 11 - Oct 12
Once the old Schools house now a newly furnished Apartment
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

8. 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 ￥18,644
￥46,089 total
includes taxes & fees
Oct 14 - Oct 15
Newly Remodeled 1-BR Close to Everything yet Very Private
A modern kitchen with a central island, bar stools, and pendant lighting.

9. 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, (34 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 ￥102,700
￥163,214 total
includes taxes & fees
Oct 14 - Oct 15
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

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 ￥26,544
￥50,276 total
includes taxes & fees
Oct 26 - Oct 27
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

11. 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 ￥18,328
￥35,929 total
includes taxes & fees
Nov 2 - Nov 3
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A hotel room with a bed, two bedside tables with lamps, a ceiling fan, a door, and a framed abstract artwork on the wall.

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

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (8 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 ￥26,473
￥67,572 total
includes taxes & fees
Oct 11 - Oct 12
The Bay Cottage · Rocky Neck Park, Beach & Niantic
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

13. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (54 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is ￥15,010
￥38,993 total
includes taxes & fees
Nov 2 - Nov 3
The SandPiper
A modern living room with a sofa, a dining table, and a massage chair.

14. #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 ￥29,406
￥73,363 total
includes taxes & fees
Oct 12 - Oct 13
#29 - Modern 5 Bedroom/2 Bath
A wooden deck with a table and chairs, overlooking a river and trees.

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

Steps to Beach • Hot Tub • Game Room • Water Views
Branford
The price is ￥126,400
￥204,136 total
includes taxes & fees
Oct 20 - Oct 21
Steps to Beach • Hot Tub • Game Room • Water Views
Veterans Park, near the house

16. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (32 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is ￥23,384
￥42,494 total
includes taxes & fees
Nov 3 - Nov 4
Family Stays: Middletown, CT
A wooden pathway leading to a beach with scattered rocks and greenery.

17. 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 ￥30,810
￥71,122 total
includes taxes & fees
Nov 3 - Nov 4
Beach Block Hideaway
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

18. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥22,910
￥50,546 total
includes taxes & fees
Oct 25 - Oct 26
Aqua Vista
An outdoor dining area with hanging lights, palm trees, and a bar.

19. 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 ￥31,442
￥48,380 total
includes taxes & fees
Oct 13 - Oct 14
American Beech in Greenport - Petite King Room 7
A beach with people relaxing, a pier extending into the water, and a clear sky.

20. 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, (33 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥22,910
￥60,836 total
includes taxes & fees
Nov 1 - Nov 2
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
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

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"It was very clean and very modern looking we like it a lot"
Dominic 1-night trip
Posted 10 hours ago
Cambria Hotel New Haven University Area

Find out more about Madison

Madison Vacation Homes information

Number of reviews
568
Accommodation
545 Vacation Homes
Lowest Price
￥38,993
Highest Price
￥204,136