Madison Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Madison holiday rentals

View from property
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Cabin in East Haddam

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (101 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is HK$850
HK$1,336 total
includes taxes & fees
15 Jan - 16 Jan
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
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$593
HK$1,516 total
includes taxes & fees
19 Jan - 20 Jan
The Stern at Soundview · Beach+Ocean+Sunrise
Interior
Westville Stay • 2BR • Near Yale • Free Parking

Apartment in West New Haven

Westville Stay • 2BR • Near Yale • Free Parking
10.0 out of 10, Exceptional, (3 reviews)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is HK$561
HK$1,739 total
includes taxes & fees
19 Jan - 20 Jan
Westville Stay • 2BR • Near Yale • Free Parking
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Holiday Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is HK$788
HK$2,299 total
includes taxes & fees
18 Jan - 19 Jan
Private Apartment in Berlin
Exterior
Charming Studio| Near Yale| Downtown New Haven

Apartment in Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (12 reviews)
"Great location, exactly as advertised. The shades are somewhat translucent, so a bit bright at night, but wore a mask and it was fine. "
United States
Scott B.
The price is HK$530
HK$1,404 total
includes taxes & fees
15 Jan - 16 Jan
Charming Studio| Near Yale| Downtown New Haven
1 bedroom, desk, iron/ironing board, travel cot
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.6 out of 10, Exceptional, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is HK$678
HK$1,465 total
includes taxes & fees
20 Jan - 21 Jan
1-bedroom cottage with Grove Beach 🏖️ access.
Interior
Beach Apartment in Woodmont Milford

Apartment in Milford

Beach Apartment in Woodmont Milford
2.0 star property
9.0 out of 10, Wonderful, (2 reviews)
"Had a great stay!"
United States
Garry G.
The price is HK$999
HK$2,962 total
includes taxes & fees
18 Jan - 19 Jan
Beach Apartment in Woodmont Milford
Smart TV, books
Rogers Lake House (87) · CT College+Beach+USCGA

Holiday Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5 reviews)
"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$674
HK$3,126 total
includes taxes & fees
27 Jan - 28 Jan
Rogers Lake House (87) · CT College+Beach+USCGA
Fridge, microwave, oven, stovetop
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Holiday Home in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
10.0 out of 10, Exceptional, (1 review)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is HK$680
HK$3,853 total
includes taxes & fees
25 Jan - 26 Jan
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Beach nearby
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Holiday Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is HK$814
HK$2,717 total
includes taxes & fees
1 Feb - 2 Feb
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Terrace/patio
Soothing 2-bedroom lower-level apartment in Berlin

Apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
10.0 out of 10, Exceptional, (1 review)
"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$968
HK$2,515 total
includes taxes & fees
20 Jan - 21 Jan
Soothing 2-bedroom lower-level apartment in Berlin
1 bedroom, free WiFi, bed sheets
Lakefront Boho Tiny House

Mobile Home in East Lyme

Lakefront Boho Tiny House
10.0 out of 10, Exceptional, (4 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is HK$687
HK$1,634 total
includes taxes & fees
15 Jan - 16 Jan
Lakefront Boho Tiny House
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.2 out of 10, Wonderful, (15 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is HK$660
HK$1,274 total
includes taxes & fees
16 Jan - 17 Jan
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Holiday Home in New Britain

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (9 reviews)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Exterior
Cozy Lakefront Tiny House

Mobile Home in East Lyme

Cozy Lakefront Tiny House
10.0 out of 10, Exceptional, (2 reviews)
"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$695
HK$1,628 total
includes taxes & fees
15 Jan - 16 Jan
Cozy Lakefront Tiny House
Fridge, microwave, oven, stovetop
One bedroom apartment in United States of America, New Haven

Apartment in Dwight

One bedroom apartment in United States of America, New Haven
9.4 out of 10, Exceptional, (3 reviews)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is HK$741
HK$1,591 total
includes taxes & fees
19 Jan - 20 Jan
One bedroom apartment in United States of America, New Haven
TV, offices
Beach Apartment in Woodmont Milford 102

Apartment in Milford

Beach Apartment in Woodmont Milford 102
2.0 star property
The price is HK$928
HK$2,848 total
includes taxes & fees
21 Jan - 22 Jan
Beach Apartment in Woodmont Milford 102
Dining
2BR Apartment Near Wesleyan 102

Apartment in Washington Street Historic District

2BR Apartment Near Wesleyan 102
2.0 star property
The price is HK$787
HK$2,305 total
includes taxes & fees
18 Jan - 19 Jan
2BR Apartment Near Wesleyan 102
Beach nearby, sun-loungers, beach towels
Beach Cottage, private beach and pass

Cottage in East Lyme

Beach Cottage, private beach and pass
10.0 out of 10, Exceptional, (9 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is HK$1,326
HK$3,115 total
includes taxes & fees
15 Jan - 16 Jan
Beach Cottage, private beach and pass
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Holiday Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$1,064
HK$3,909 total
includes taxes & fees
20 Jan - 21 Jan
Beachside Bliss w/ Game Room, Gym & Golf Green
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

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"I arrived earlier than planned and earlier than check-in time, so understandably my room was not available, but I was asked to come back in an hour or so and it would be - I came back and it was ready and it was prior to check-in time. Very nice. The room was also clean. The lobby smells great and is very clean!"
Michele 1-night trip
Posted 11 hours ago
Cambria Hotel New Haven University Area

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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This holiday home rental outside of Madison offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, 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?

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 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.