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

Madison Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Madison holiday rentals

Sun-loungers, beach towels

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
The price is HK$1,235
HK$2,837 total
includes taxes & fees
14 Jul - 15 Jul
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.6 out of 10, Exceptional, (163 reviews)
"Great experience at usual."
United States
Andrea
The price is HK$1,058
HK$1,578 total
includes taxes & fees
11 Aug - 12 Aug
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
1 bedroom, desk, iron/ironing board, travel cot

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (47 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$1,122
HK$2,026 total
includes taxes & fees
13 Jul - 14 Jul
1-bedroom cottage with Grove Beach 🏖️ access.
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (30 reviews)
"Great stay & great staff!"
United States
James
The price is HK$3,203
HK$3,659 total
includes taxes & fees
27 Jul - 28 Jul
North Fork Resort
1 bedroom, desk, iron/ironing board, WiFi

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 HK$533
HK$1,356 total
includes taxes & fees
13 Jul - 14 Jul
One bedroom in United States of America, New Haven
TV

Modern Westville Home Near Yale University

Modern Westville Home Near Yale University
West New Haven
The price is HK$914
HK$2,151 total
includes taxes & fees
29 Jul - 30 Jul
Modern Westville Home Near Yale University
TV

Tiny, Budget Friendly 1 Bedroom Central CT

Tiny, Budget Friendly 1 Bedroom Central CT
Southington
The price is HK$830
HK$1,770 total
includes taxes & fees
19 Jul - 20 Jul
Tiny, Budget Friendly 1 Bedroom Central CT
TV

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.
Newly Remodeled 1-BR Close to Everything yet Very Private
Dining

Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (77 reviews)
"Spacious"
United States
Mehul
The price is HK$1,019
HK$1,819 total
includes taxes & fees
19 Jul - 20 Jul
Spacious 2 Bedroom apartment close to Yale Bowl
Exterior

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is HK$1,023
HK$2,546 total
includes taxes & fees
13 Jul - 14 Jul
Angelica’s safe haven @ west haven
1 bedroom, iron/ironing board, WiFi, bed sheets

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 HK$925
HK$2,287 total
includes taxes & fees
13 Jul - 14 Jul
Once the old Schools house now a newly furnished Apartment
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (269 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is HK$3,519
HK$4,361 total
includes taxes & fees
14 Jul - 15 Jul
Cliffside Resort Condominiums
Property grounds

#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 HK$1,669
HK$3,229 total
includes taxes & fees
5 Aug - 6 Aug
#24 *Serenity* A Lakefront Cottage Retreat
Smart TV, books

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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (8 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.
The price is HK$1,435
HK$4,126 total
includes taxes & fees
16 Jul - 17 Jul
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is HK$1,152
HK$2,238 total
includes taxes & fees
13 Jul - 14 Jul
The Stern at Soundview · Beach+Ocean+Sunrise
Exterior

Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (14 reviews)
"Conveniently located and nice, practically appointed stay for a business trip to work with a collaborator in town."
United States
Jeremy Y.
The price is HK$847
HK$1,924 total
includes taxes & fees
13 Jul - 14 Jul
Bright Downtown Studio near Yale & East Rock!
Lobby

Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very good, (8 reviews)
"The place was incredibly clean. The instructions were clear for entering and locking up. Great experience! Thanks Dylan. "
United States
Andrew P.
The price is HK$882
HK$2,000 total
includes taxes & fees
23 Jul - 24 Jul
Spacious Bohemian Nook
Smart TV

Luxury Loft •Pool • Gym • Free Parking • Near Yale

Luxury Loft •Pool • Gym • Free Parking • Near Yale
Orange
The price is HK$1,079
HK$2,053 total
includes taxes & fees
12 Aug - 13 Aug
Luxury Loft •Pool • Gym • Free Parking • Near Yale
Interior

Lakefront Home, Close to Mt Southington!

Lakefront Home, Close to Mt Southington!
3.0 star property
Wolcott
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house with great views of the lake. "
United States
Darrell
The price is HK$1,591
HK$3,732 total
includes taxes & fees
28 Jul - 29 Jul
Lakefront Home, Close to Mt Southington!
Dining

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
The price is HK$1,694
HK$3,054 total
includes taxes & fees
31 Jul - 1 Aug
1 Min to I-91 - Newly Renovated Modern 2 BR Home
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

Find out more about Madison

Search for holiday rentals in Madison on Expedia! You can easily find your home rentals, villas, holiday apartments in Madison using one of the methods below:

  • View our selection of featured holiday rentals in Madison
  • Use the map to find apartments and other holiday homes in the Madison neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Madison while they last

Look no further and take a look at our great range of rental properties in Madison!

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals in Madison close to RJ Julia Booksellers, or you can select a more secluded 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 holiday rentals that Madison has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This highly rated holiday home rental in Madison is located on the beach, and has a balcony, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Madison?

With 32 Expedia holiday rentals, you're guaranteed 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 holiday rental in Madison like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madison. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.