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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Our top choices for Madison holiday homes

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (4 reviews)
"Very lovely home! We very much enjoyed our stay and hope to be back again!"
United States
Morgan M.
The price is AU$801
includes taxes & fees
10 Nov - 11 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green

2. Charming beach home, complete with pool & cozy guest house!

Charming beach home, complete with pool & cozy guest house!
Clinton
9.8 out of 10, Exceptional, (56 reviews)
"Beautiful, open and clean. Perfect for a family stay!"
United States
Juliana A.
The price is AU$1,880
includes taxes & fees
12 Nov - 13 Nov
Charming beach home, complete with pool & cozy guest house!

3. 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 AU$884
includes taxes & fees
8 Nov - 9 Nov
Historic New England home ,Reunions Beach pass

4. 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 AU$776
includes taxes & fees
16 Nov - 17 Nov
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

5. 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 AU$225
includes taxes & fees
9 Nov - 10 Nov
Cozy East Haven Home • Near Beach & Yale

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 AU$419
includes taxes & fees
12 Nov - 13 Nov
Once the old Schools house now a newly furnished Apartment

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 AU$1,619
includes taxes & fees
5 Nov - 6 Nov
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

8. 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 AU$316
includes taxes & fees
9 Nov - 10 Nov
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

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 AU$667
includes taxes & fees
23 Nov - 24 Nov
#29 - Modern 5 Bedroom/2 Bath

10. 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 AU$196
includes taxes & fees
28 Nov - 29 Nov
NEW private studio 1.1 miles to beach in East Lyme

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 AU$428
includes taxes & fees
5 Nov - 6 Nov
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

12. 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 AU$387
includes taxes & fees
16 Nov - 17 Nov
Family Stays: Middletown, CT

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

Steps to Beach • Hot Tub • Game Room • Water Views
Branford
The price is AU$1,706
includes taxes & fees
8 Nov - 9 Nov
Steps to Beach • Hot Tub • Game Room • Water Views

14. 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 AU$331
includes taxes & fees
10 Nov - 11 Nov
The SandPiper

15. 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 AU$602
includes taxes & fees
12 Nov - 13 Nov
Beach Block Hideaway

16. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AU$348
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista

17. 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 AU$705
includes taxes & fees
8 Nov - 9 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

18. 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 AU$488
includes taxes & fees
5 Nov - 6 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

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 AU$409
includes taxes & fees
5 Nov - 6 Nov
American Beech in Greenport - Petite King Room 7

20. Las Casitas Retreat

Las Casitas Retreat
East Shore
10.0 out of 10, Exceptional, (1 review)
"La Caistas Retreat was a wonderful experience. The place was very clean and cozy. We visited with 2 of my adult children and their significant others and had plenty of room. The host, Sujata, was very informative amd checked in daily. The check-in and out were very smooth. I would recommend this place to anyone visiting New Haven!!!!"
United States
Tim H.
The price is AU$892
includes taxes & fees
5 Nov - 6 Nov
Las Casitas Retreat
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

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Madison Holiday Homes information

Number of reviews
543
Accommodation
545 Holiday Homes
Lowest Price
AU$225
Highest Price
AU$1,880