Madison Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Madison

Exterior
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison
10.0 out of 10, Exceptional, (36)
"The place was adorable and spotless, the beds were super comfortable it was perfect and a minute from the beach! We will be back. Thanks for a great time!"
United States
Edward
The price is HK$1,679
HK$2,149 total
includes taxes & fees
17 Nov - 18 Nov
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Exterior
Cozy Lakefront Tiny House

Cozy Lakefront Tiny House

East Lyme
10.0 out of 10, Exceptional, (2)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
United States
Rebecca K.
The price is HK$616
HK$1,534 total
includes taxes & fees
18 Nov - 19 Nov
Cozy Lakefront Tiny House
1 bedroom, free WiFi, bed sheets
Lakefront Boho Tiny House

Lakefront Boho Tiny House

East Lyme
10.0 out of 10, Exceptional, (3)
"My husband has always wanted to try a tiny house. This place exceeded our expectations. Lovely house. Lovely lake. He was in heaven fishing and kayaking "
United States
Asha A.
The price is HK$847
HK$1,799 total
includes taxes & fees
9 Dec - 10 Dec
Lakefront Boho Tiny House
Free WiFi, bed sheets
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
9.4 out of 10, Exceptional, (6)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is HK$1,470
HK$1,680 total
includes taxes & fees
17 Nov - 18 Nov
North Fork Cottages & RV Resort
Exterior
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, (80)
"Very nice cabins "
United States
Jairo
The price is HK$1,003
HK$1,511 total
includes taxes & fees
19 Nov - 20 Nov
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"Perfect for a weekend beach getaway. Very small but accurately portrayed in the pictures. It was clean and the host was very helpful and responsive. "
United States
Olivia C.
The price is HK$591
HK$1,511 total
includes taxes & fees
18 Nov - 19 Nov
The Stern at Soundview · Beach+Ocean+Sunrise
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

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

Old Lyme
10.0 out of 10, Exceptional, (3)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is HK$671
HK$3,130 total
includes taxes & fees
17 Nov - 18 Nov
Rogers Lake House (87) · CT College+Beach+USCGA
Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

East Rock
9.6 out of 10, Exceptional, (10)
"The location was ideal for walking to Yale and out to coffee and dinner. The unit is large, we had plenty of room to spread out and have privacy and the kitchen and living room are perfect for eating and relaxing. We had a great time. "
United States
sarah F.
The price is HK$637
HK$1,951 total
includes taxes & fees
18 Nov - 19 Nov
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Cheshire
9.2 out of 10, Wonderful, (11)
"Very nice location in a country setting. Saw deer in the backyard every morning. Very clean and accurate description of the property. Friendly hosts who supplied everything we needed. Would stay here again. Highly recommend."
United States
Eileen A.
The price is HK$658
HK$1,269 total
includes taxes & fees
17 Nov - 18 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Outdoor dining
Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Berlin
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is HK$700
HK$2,163 total
includes taxes & fees
17 Nov - 18 Nov
Soothing 2-bedroom lower-level apartment in Berlin
TV
All New Private and Cozy in great location

All New Private and Cozy in great location

Wallingford
8.8 out of 10, Excellent, (6)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is HK$715
HK$2,012 total
includes taxes & fees
21 Nov - 22 Nov
All New Private and Cozy in great location
Outdoor dining
Cozy Shoreline Stay

Cozy Shoreline Stay

Branford Center
10.0 out of 10, Exceptional, (11)
"Really nice space for single or couple and convenient to access and stay - just perfect for overnight when visiting family locally!"
United States
Kathleen O.
The price is HK$933
HK$1,953 total
includes taxes & fees
27 Nov - 28 Nov
Cozy Shoreline Stay
Dining
#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

Middletown
9.8 out of 10, Exceptional, (20)
"Great stay while our son moved into Wesleyan University. It was a nice alternative to staying at one of the local hotels. Clean and comfortable. We love the deck off the back with serene views of that lake. 5 minute drive to Wesleyan University. Will stay again for sure. "
United States
Allison C.
The price is HK$1,023
HK$2,420 total
includes taxes & fees
17 Nov - 18 Nov
#24 *Serenity* A Lakefront Cottage Retreat
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green

2.0 star property
Westbrook
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$949
HK$3,791 total
includes taxes & fees
2 Dec - 3 Dec
Beachside Bliss w/ Game Room, Gym & Golf Green
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)
"The fact that it was listed with a hot tub and there wasn't one was very disappointing! Clean and cute. Location was convenient. Could use a better bed and pillows. It was a good place to stay,"
United States
Robert K.
The price is HK$715
HK$2,012 total
includes taxes & fees
17 Nov - 18 Nov
Once the old Schools house now a newly furnished Apartment
Beach nearby
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme
9.6 out of 10, Exceptional, (52)
"Great stay, charming cottage, hope to return"
United States
Ellen C.
The price is HK$756
HK$1,948 total
includes taxes & fees
30 Nov - 1 Dec
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Interior
Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale

Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale

East Rock
9.4 out of 10, Exceptional, (3)
"Met all expectations and the location is excellent."
United States
James D.
The price is HK$894
HK$2,633 total
includes taxes & fees
9 Dec - 10 Dec
Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Private Apartment in Berlin

2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is HK$909
HK$2,457 total
includes taxes & fees
17 Nov - 18 Nov
Private Apartment in Berlin
Interior
Stylish City Living|Wooster Square|Downtown Views

Stylish City Living|Wooster Square|Downtown Views

Downtown New Haven
9.6 out of 10, Exceptional, (5)
"The unit is beautifully done. Our family of 6 had just the right amount of space. Perfect for walking around the city and lots of great food choices close by. "
United States
Kelly E.
The price is HK$762
HK$2,114 total
includes taxes & fees
17 Nov - 18 Nov
Stylish City Living|Wooster Square|Downtown Views
Exterior
Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center

Wallingford
10.0 out of 10, Exceptional, (2)
"Felt like coming home. Moved out of state 20 yrs ago. "
United States
Beth C.
The price is HK$715
HK$2,012 total
includes taxes & fees
8 Dec - 9 Dec
Newly Remodeled with deck. Close to town center
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

10/10 Excellent
"room was clean and service was excellant. Front desk staff great and very helpful"
Michael 1-night trip
Posted 2 days 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?

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food: This holiday home rental outside of Madison is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 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 patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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?

Family-friendly attractions include RJ Julia Booksellers and Anna Mia's, whereas Hammonasset Beach and Meigs Point Nature Center are a couple of great spots to enjoy the outdoors. Hammonasset Beach State Park and Allis-Bushnell House and Museum 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.