Madison Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Madison vacation rentals

Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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, (95)
"My wife loved it…she has a rough week with work and just life in general, so I wanted to do something nice for her and surprised her with a stay here…she was really happy and loved everything about it…can’t wait to do this again 😊"
United States
Keven
The price is ￥18,560
￥28,519 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is ￥11,860
￥30,157 total
includes taxes & fees
Jan 3 - Jan 4, 2026
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.2 out of 10, Wonderful, (36)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is ￥12,322
￥27,872 total
includes taxes & fees
Jan 5 - Jan 6, 2026
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
East Rock
10.0 out of 10, Exceptional, (4)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
The price is ￥22,460
￥58,505 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (5)
"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 ￥13,468
￥62,491 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Rogers Lake House (87) · CT College+Beach+USCGA
Fridge, microwave, oven, stovetop
Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford
2.0 star property
Milford
9.0 out of 10, Wonderful, (2)
"Had a great stay!"
United States
Garry G.
The price is ￥19,964
￥59,846 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Beach Apartment in Woodmont Milford
Exterior detail
Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (34)
"The place was spotless and comfortable. Would highly recommend!"
United States
Jeanne Y.
The price is ￥18,560
￥33,432 total
includes taxes & fees
Jan 29 - Jan 30, 2026
Walk To Goodspeed Opera House!
Fridge, microwave, oven, stovetop
The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
East Lyme
9.0 out of 10, Wonderful, (4)
"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 ￥18,492
￥57,171 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is ￥13,387
￥25,729 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

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)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
The price is ￥14,817
￥41,246 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Exterior
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
10.0 out of 10, Exceptional, (54)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is ￥70,187
￥127,038 total
includes taxes & fees
Jan 3 - Jan 4, 2026
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Fridge, microwave, oven, stovetop
Adorable Cottage, 5 min walk to water & town

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)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥27,218
￥65,199 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Adorable Cottage, 5 min walk to water & town
Private kitchen
Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking
West New Haven
10.0 out of 10, Exceptional, (3)
"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 ￥13,308
￥37,576 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Westville Stay • 2BR • Near Yale • Free Parking
Dining
#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
The price is ￥38,986
￥72,390 total
includes taxes & fees
Dec 31 - Jan 1, 2026
#24 *Serenity* A Lakefront Cottage Retreat
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
Downtown New Haven
9.0 out of 10, Wonderful, (12)
"Convenient location. Just off Rte 91. Easy street parking. The studio is as pictured - exposed brick walls, high ceilings. Everything you need for a short stay. "
United States
Lois G.
The price is ￥15,031
￥32,723 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Charming Studio| Near Yale| Downtown New Haven
Exterior
Cozy Lakefront Tiny House

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 ￥16,127
￥35,742 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cozy Lakefront Tiny House
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

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 ￥14,583
￥68,904 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior
The Nest At Elm City Flats.

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
9.4 out of 10, Exceptional, (6)
"Nice place! Short but sweet trip. Appreciate how quick your communication was and your accommodations!"
United States
Lori K.
The price is ￥13,897
￥37,077 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Nest At Elm City Flats.
1 bedroom, free WiFi, bed sheets
Lakefront Boho Tiny House

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (3)
"this place was amazing i would come again"
United States
Tatyanna R.
The price is ￥15,269
￥34,600 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Lakefront Boho Tiny House
Fridge, microwave, oven, stovetop
Beach Cottage, private beach and pass

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (9)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is ￥36,778
￥74,401 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Beach Cottage, private beach and pass
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

Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

10/10 Excellent
"A"
Naomi 2-night trip
Posted 2 days ago
Hamden Hotel and Suites – Hamden New 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!

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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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This vacation home rental outside 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 you can cook with friends or family.

How many vacation rentals are there in Madison?

With 32 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?

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 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.