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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Madison vacation rentals

A beach with a house in the background, a clear sky, and a calm sea.

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
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is AED 579
AED 1,230 total
includes taxes & fees
8 Nov - 9 Nov
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (66 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 485
AED 862 total
includes taxes & fees
9 Nov - 10 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

3. 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, (31 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is AED 744
AED 1,253 total
includes taxes & fees
5 Nov - 6 Nov
The gardners Cottage 1 mile from long Island Sound - pet friendly
A cabin with a dining table set for two, a bicycle, and a small porch area.

4. 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, (216 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is AED 466
AED 705 total
includes taxes & fees
3 Dec - 4 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

5. 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 AED 786
AED 2,043 total
includes taxes & fees
10 Nov - 11 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green
A modern living room with a large TV, white cabinetry, and a view of the outdoors.

6. 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 AED 2,523
AED 4,798 total
includes taxes & fees
12 Nov - 13 Nov
Charming beach home, complete with pool & cozy guest house!
A hotel room with two beds, a desk, and a chair.

7. Spacious 2 Full Beds Nsmk

Spacious 2 Full Beds Nsmk
Branford
10.0 out of 10, Exceptional, (52 reviews)
"Really appreciated the clean, spacious feel throughout my stay."
United States
Anonymous traveler
The price is AED 290
AED 333 total
includes taxes & fees
2 Dec - 3 Dec
Spacious 2 Full Beds Nsmk
A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

8. 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 AED 1,102
AED 2,178 total
includes taxes & fees
5 Nov - 6 Nov
Historic New England home ,Reunions Beach pass
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

9. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
The price is AED 895
AED 2,078 total
includes taxes & fees
5 Nov - 6 Nov
Adorable Cottage with Cottage porch, walk to water & town
A balcony with a view of the ocean, a lawn, and a house in the background.

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is AED 621
AED 1,117 total
includes taxes & fees
15 Nov - 16 Nov
Cliffside Resort Condominiums
A large, white, multi-story building with a prominent tower and a flag on top.

11. 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 547
AED 899 total
includes taxes & fees
30 Nov - 1 Dec
Walk To Goodspeed Opera House!
A modern house with a deck, outdoor seating, and a fire pit.

12. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (72 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is AED 1,141
AED 1,303 total
includes taxes & fees
12 Nov - 13 Nov
North Fork Resort
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

13. 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 1,091
AED 2,017 total
includes taxes & fees
16 Nov - 17 Nov
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

14. 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, (40 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 459
AED 925 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A living room with a dark grey sofa, a wooden coffee table with a vase of white flowers, a patterned rug, and a ceiling fan.

15. 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 AED 420
AED 501 total
includes taxes & fees
8 Nov - 9 Nov
Cozy East Haven Home • Near Beach & Yale
A two-story house with a covered porch, a front door, and a small outdoor seating area with a table and chairs.

16. Cozy Home near private beach , close to New Haven area colleges Hospitals

Cozy Home near private beach , close to New Haven area colleges Hospitals
Branford
9.4 out of 10, Exceptional, (86 reviews)
"Property was clean with some nice cozy touches. Wine on the table, fruit in the frig, chocolate for comfort, coffee for wakeup. Host was very pleasant and accommodating. Will definitely stay there again."
United States
Vincent
The price is AED 403
AED 1,062 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Home near private beach , close to New Haven area colleges Hospitals
A reception desk with a staff member, a guest, and a child.

17. Cozy 1 King Bed | Smoking

Cozy 1 King Bed | Smoking
Branford
10.0 out of 10, Exceptional, (55 reviews)
"Before morning travel, we got much-needed rest here. Rooms had ample space so it didn't feel cramped at all, plus friendly staff shared helpful breakfast recommendations as part of our group treat experience."
United States
Anonymous traveler
The price is AED 290
AED 333 total
includes taxes & fees
1 Dec - 2 Dec
Cozy 1 King Bed | Smoking
A hotel reception area with a receptionist, a guest, and a child.

18. Cozy 2 Full Beds|Free Parking & Wifi

Cozy 2 Full Beds|Free Parking & Wifi
Niantic
10.0 out of 10, Exceptional, (55 reviews)
"Close to local spots, good value for what you get."
United States
Anonymous traveler
The price is AED 297
AED 342 total
includes taxes & fees
5 Nov - 6 Nov
Cozy 2 Full Beds|Free Parking & Wifi
A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

19. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
9.6 out of 10, Exceptional, (4 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
The price is AED 580
AED 1,255 total
includes taxes & fees
6 Nov - 7 Nov
2BR Apartment Near Wesleyan 301
A reception desk with a staff member, a guest, and a child.

20. 1 King Bed | Nsmk, Micfridge

1 King Bed | Nsmk, Micfridge
Branford
10.0 out of 10, Exceptional, (52 reviews)
"The location is convenient with easy access to local shops and restaurants nearby."
United States
Anonymous traveler
The price is AED 304
AED 350 total
includes taxes & fees
1 Dec - 2 Dec
1 King Bed | Nsmk, Micfridge
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

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"It was a good location. Would be nice to have coffee for guest in the morning - no one really likes to make it in the room."
Alycia and or Mike 1-night trip
Posted 11 hours ago
Hotel Marcel New Haven, Tapestry Collection By Hilton

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 Scranton Memorial Library 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.