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

Madison Vacation Rentals

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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 vacation rentals

Sun loungers, beach towels

1. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is AED 545
AED 1,247 total
includes taxes & fees
28 Sep - 29 Sep
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
TV, books

2. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (95 reviews)
"Great cottage on the Sound!"
United States
David S.
Direct waterfront renovated cottage.
1 bedroom, desk, iron/ironing board, travel crib

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (59 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 443
AED 843 total
includes taxes & fees
6 Oct - 7 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
Coffee/tea maker, fridge, microwave, oven

4. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is AED 643
AED 1,140 total
includes taxes & fees
7 Oct - 8 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
Cabin, 1 Queen Bed | Private kitchen | Mini-fridge, stovetop, cookware/dishes/utensils, paper towels

5. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (190 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is AED 474
AED 714 total
includes taxes & fees
21 Sep - 22 Sep
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Beach nearby

6. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is AED 502
AED 1,205 total
includes taxes & fees
29 Sep - 30 Sep
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Interior

7. 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 AED 608
AED 1,732 total
includes taxes & fees
21 Sep - 22 Sep
Adorable Cottage, 5 min walk to water & town
Beach

8. 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 AED 901
AED 2,378 total
includes taxes & fees
23 Sep - 24 Sep
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio

9. 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 AED 1,128
AED 2,391 total
includes taxes & fees
30 Sep - 1 Oct
Historic New England home ,Reunions Beach pass
Flat-screen TV

10. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (56 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is AED 1,040
AED 1,188 total
includes taxes & fees
21 Oct - 22 Oct
North Fork Resort
Interior

11. 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 AED 1,058
AED 2,067 total
includes taxes & fees
21 Sep - 22 Sep
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Smart TV, fireplace, books, music library

12. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (37 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is AED 492
AED 982 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Beach nearby

13. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Great spot Very clean"
United States
Dorothy W.
The price is AED 705
AED 1,685 total
includes taxes & fees
29 Sep - 30 Sep
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Exterior

14. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveler
The price is AED 489
AED 861 total
includes taxes & fees
6 Oct - 7 Oct
Walk To Goodspeed Opera House!
Condo | Terrace/patio

15. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (292 reviews)
"Great place!"
United States
Christine
The price is AED 1,011
AED 1,563 total
includes taxes & fees
5 Oct - 6 Oct
Cliffside Resort Condominiums
Beach nearby

16. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.0 out of 10, Very good, (5 reviews)
"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."
United States
Janine
The price is AED 554
AED 1,058 total
includes taxes & fees
24 Sep - 25 Sep
The Stern at Soundview · Beach+Ocean+Sunrise
1 bedroom, desk, iron/ironing board, WiFi

17. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
The price is AED 294
AED 690 total
includes taxes & fees
27 Sep - 28 Sep
One bedroom in United States of America, New Haven
Interior

18. VintageGem: Prime East Rock 5 mins to Yale 5 beds

VintageGem: Prime East Rock 5 mins to Yale 5 beds
East Rock
9.4 out of 10, Exceptional, (3 reviews)
"Met all expectations and the location is excellent."
United States
James D.
The price is AED 1,627
AED 2,797 total
includes taxes & fees
3 Oct - 4 Oct
VintageGem: Prime East Rock 5 mins to Yale 5 beds
1 bedroom, iron/ironing board, WiFi, bed sheets

19. 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 AED 433
AED 1,071 total
includes taxes & fees
21 Sep - 22 Sep
Once the old Schools house now a newly furnished Apartment
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

8/10 Good
"I didn't Ike the breakfast"
Robin 2-night trip
Posted 4 hours ago
Best Western Executive Hotel Of New Haven - West Haven

Frequently asked questions

Are there vacation rentals in Madison?

Yes, we offer vacation rentals in Madison close to RJ Julia Booksellers, or you can go with a more remote option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Madison. Make sure you have time to check out the aquarium and waterfront during your trip.

What are some of the best vacation home rentals that Madison has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This highly rated vacation home rental in Madison is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Madison is Waterfront Estate Home - Pool and Private Beach Pavilion - East.

How many vacation rentals are there in Madison?

With 36 Expedia vacation rentals, you're sure to find just the right place for your Madison stay.

What’s there to see and do in Madison?

Hammonasset Beach and Meigs Point Nature Center are a couple of scenic spots to enjoy the outdoors, whereas Allis-Bushnell House and Museum is one of the cultural attractions. Hammonasset Beach State Park and North Madison Shopping Center are other places to visit while you're in town.

What’s a vacation rental in Madison like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Madison. Vacation rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.