Sunset behind a frozen Madison, WI

Madison Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Madison holiday rentals

View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (156 reviews)
"Great stay! "
United States
Tanitra
The price is HK$1,246
HK$1,793 total
includes taxes & fees
22 Jun - 23 Jun
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, (45 reviews)
"The place was super cozy and the host was wonderful! "
United States
Philip L.
The price is HK$1,051
HK$1,952 total
includes taxes & fees
26 Jun - 27 Jun
1-bedroom cottage with Grove Beach 🏖️ access.
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is HK$1,291
HK$2,754 total
includes taxes & fees
16 Jun - 17 Jun
#24 *Serenity* A Lakefront Cottage Retreat
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (23 reviews)
"Great stay & great staff!"
United States
James
The price is HK$2,292
HK$2,618 total
includes taxes & fees
16 Jun - 17 Jun
North Fork Resort
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (256 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is HK$1,457
HK$2,005 total
includes taxes & fees
16 Jun - 17 Jun
Cliffside Resort Condominiums
Beach nearby

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is HK$1,474
HK$2,662 total
includes taxes & fees
21 Jun - 22 Jun
The Stern at Soundview · Beach+Ocean+Sunrise
Fridge, microwave, oven, stovetop

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
8.0 out of 10, Very good, (5 reviews)
"Great place to stay! Host was quick to answer and the check in process was so easy! "
United States
Payton P.
The price is HK$548
HK$1,373 total
includes taxes & fees
16 Jun - 17 Jun
One bedroom in United States of America, New Haven
Banquet hall

Beautiful Downtown New Haven Retreat

Beautiful Downtown New Haven Retreat
Downtown New Haven
The price is HK$932
HK$2,497 total
includes taxes & fees
18 Jun - 19 Jun
Beautiful Downtown New Haven Retreat
Interior

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$1,224
HK$2,481 total
includes taxes & fees
23 Jun - 24 Jun
1 Min to I-91 - Newly Renovated Modern 2 BR Home
Interior

Modern Studio Retreat

Modern Studio Retreat
Dwight
The price is HK$1,112
HK$1,770 total
includes taxes & fees
11 Jul - 12 Jul
Modern Studio Retreat
Smart TV, fireplace, books, offices

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is HK$1,661
HK$3,662 total
includes taxes & fees
16 Jun - 17 Jun
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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)
"We had a very nice stay at Roger’s Lake! The house was so cool! It had all the amenities we needed and the location was charming and peaceful. In particular, the beds are really comfortable! They have this awesome exercise room where you can stretch out and enjoy the light. The host, Peter, was especially easy to work with and was very communicative. My family and I are hoping to come back soon for another stay."
United States
Andrea
The price is HK$1,474
HK$4,178 total
includes taxes & fees
28 Jun - 29 Jun
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (59 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
Insta-worthy Couples Retreat: Perfect for romantic getaway!
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, (13 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$2,270 total
includes taxes & fees
16 Jun - 17 Jun
Once the old Schools house now a newly furnished Apartment
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (38 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is HK$1,528
HK$2,443 total
includes taxes & fees
16 Jun - 17 Jun
Walk To Goodspeed Opera House!
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, (73 reviews)
"Spacious"
United States
Mehul
The price is HK$1,019
HK$1,810 total
includes taxes & fees
16 Jun - 17 Jun
Spacious 2 Bedroom apartment close to Yale Bowl
Exterior

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is HK$1,052
HK$2,089 total
includes taxes & fees
16 Jun - 17 Jun
Cozy Lakefront Tiny House
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (10 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is HK$925
HK$2,286 total
includes taxes & fees
23 Jun - 24 Jun
All New 1BR with tons of Charm
Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is HK$1,307
HK$3,207 total
includes taxes & fees
16 Jun - 17 Jun
Adorable Cottage, 5 min walk to water & town
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$1,136
HK$2,676 total
includes taxes & fees
16 Jun - 17 Jun
Angelica’s safe haven @ west haven
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
"Clean, helpful staff, decent breakfast. Only reason I didnt give 5 stars was due to traffic noise as it's next to the I-95"
Kevin 1-night trip
Posted 8 hours ago
Best Western Executive Hotel Of New Haven - West Haven

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?

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12: This holiday home rental outside of Madison is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Madison?

With 34 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 East Wharf Beach Park 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.