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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Madison holiday homes

Interior

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

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (16 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
Adorable Cottage, 5 min walk to water & town
Beach

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio

3. PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Clinton
10.0 out of 10, Exceptional, (30 reviews)
"My family and I really enjoyed our stay here. I would recommend this property & location to others."
United States
Erwin U.
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Terrace/patio

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 €551
includes taxes & fees
11 Aug - 12 Aug
Historic New England home ,Reunions Beach pass
Interior

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, (139 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is €597
includes taxes & fees
2 Aug - 3 Aug
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Terrace/patio

6. Hollow Brook Estate

Hollow Brook Estate
Killingworth
10.0 out of 10, Exceptional, (2 reviews)
"Large property with multiple entertaining spaces in a peaceful and secluded setting."
United States
Thomas D.
Hollow Brook Estate
Interior

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
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is €904
includes taxes & fees
10 Aug - 11 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
1 bedroom, iron/ironing board, WiFi, bed sheets

8. 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 €261
includes taxes & fees
27 Aug - 28 Aug
Once the old Schools house now a newly furnished Apartment
Smart TV, books

9. Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (9 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
United States
Cheryl H.
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV, books

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

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (12 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is €517
includes taxes & fees
2 Aug - 3 Aug
Clear LI Sound waterview, Wedding pics, Yale&Beach
TV

11. 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)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
The price is €258
includes taxes & fees
1 Aug - 2 Aug
Newly Remodeled 1-BR Close to Everything yet Very Private
Exterior

12. Beach House

Beach House
East Lyme
9.6 out of 10, Exceptional, (61 reviews)
"Joseph was an excellent, very responsive host. House was very clean and well appointed. We had an excellent time there with our family. "
United States
Enrique
Beach House
Interior

13. 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.
The price is €267
includes taxes & fees
1 Aug - 2 Aug
Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven
Dining

14. 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, (39 reviews)
"Enjoyed our stay"
United States
Nicole L.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Property grounds

15. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
United States
Rodrigo C.
The price is €320
includes taxes & fees
5 Aug - 6 Aug
#24 *Serenity* A Lakefront Cottage Retreat
Terrace/patio

16. Oceanfront Couples Retreat - Pvt Beach + Firepit

Oceanfront Couples Retreat - Pvt Beach + Firepit
Morgan Point
9.8 out of 10, Exceptional, (16 reviews)
"Gorgeous location on LI sound! The home was perfect for us. We had plenty of room to spread out and we relax. We enjoyed the deck and the bar area! We all slept very well and we actually loved watching the planes overhead! Lots of fun spots nearby to explore and are already hoping to come back in the fall. "
United States
Carrie R.
The price is €931
includes taxes & fees
7 Aug - 8 Aug
Oceanfront Couples Retreat - Pvt Beach + Firepit
Coffee/tea maker, fridge, microwave, oven

17. Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is €491
includes taxes & fees
30 Aug - 31 Aug
Coastal Landing Stay
Marina

18. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is €315
includes taxes & fees
3 Aug - 4 Aug
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Exterior

19. Peaceful Private Stay in Shared Home Near Yale

Peaceful Private Stay in Shared Home Near Yale
West New Haven
10.0 out of 10, Exceptional, (1 review)
"This place was just perfect for us and our stay. The neighborhood was safe, and the property was easy to find. Bedroom was cozy, and the communication with the host was phenomenal. Thank you!"
United States
McKenna S.
The price is €183
includes taxes & fees
30 Aug - 31 Aug
Peaceful Private Stay in Shared Home Near Yale
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

Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

8/10 Good
"It was a clean room everything worked snd parking was great ty bill"
William 6-night trip
Posted 8 hours ago
Motel 6 Wethersfield, CT - Hartford

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