Madison Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Tonight
Nov 3 - Nov 4
Tomorrow
Nov 4 - Nov 5
This weekend
Nov 7 - Nov 9
Next weekend
Nov 14 - Nov 16

Vacation 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
10.0 out of 10, Exceptional, (35)
"Had a great time. Place was very clean and centrally located. Host was very responsive!"
United States
Patty L.
$280 nightly
The price is $317
Nov 4 - Nov 5
Total with taxes and fees
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (78)
"Very nice cabins "
United States
Jairo
$179 nightly
The price is $206
Nov 4 - Nov 5
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Beach nearby
Cliffside Resort Condominiums
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (245)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
United States
dean
$262 nightly
The price is $299
Nov 17 - Nov 18
Total with taxes and fees
Cliffside Resort Condominiums
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining
Luxury Furnished Apartments by Hyatus Downtown at Yale
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
9.6 out of 10, Exceptional, (60)
"Wonderful property- brand new building, nice spacious rooms perfect for family. Instructors for check in and out and everything in between very clear and helpful. "
United States
Zhuo
Luxury Furnished Apartments by Hyatus Downtown at Yale
Interior
Rustic Lakeside Cabin at White Gate Farm
Rustic Lakeside Cabin at White Gate Farm
10.0 out of 10, Exceptional, (122)
"Beautiful cabin on the lake. Will definitely stay again. Easy check-in easy check out. You wont regret staying here!"
United States
James N.
Rustic Lakeside Cabin at White Gate Farm
Outdoor pool
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
10.0 out of 10, Exceptional, (106)
"We had such an amazing time here and are planning to return for our next family vacation! The house was clean and spacious and the communication was phenomenal. Everyone we interacted with at the farm was kind, caring, and helpful. There is so much to do at the farm and in the surrounding area. We could not recommend this place more! Best vacation ever!"
United States
Adrienne N.
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.
1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
$164 nightly
The price is $185
Nov 4 - Nov 5
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Outdoor dining
DIRECT WATERFRONT with awesome views and near Yale
DIRECT WATERFRONT with awesome views and near Yale
10.0 out of 10, Exceptional, (2)
"Great place to stay! Easy for an overnight for a family wedding!"
United States
Phoebe T.
$406 nightly
The price is $459
Nov 10 - Nov 11
Total with taxes and fees
DIRECT WATERFRONT with awesome views and near Yale
Exterior
Shoreline Oasis
Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"Cute apartment in a house, separate from the hosts space downstairs. Clean and walking distance to some great harbor-front restaurants. 1 bed and 2 couches (no pull-out couch)"
United States
Molly H.
$230 nightly
The price is $261
Nov 4 - Nov 5
Total with taxes and fees
Shoreline Oasis
Fridge, microwave, oven, stovetop
Private Apartment in Berlin
Private Apartment in Berlin
2.0 star property
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.
$279 nightly
The price is $316
Nov 5 - Nov 6
Total with taxes and fees
Private Apartment in Berlin
Exterior
Charming Studio| Near Yale| Downtown New Haven
Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (9)
"Nice location in downtown New Haven. The room itself is nice and convenient. The window near the bed does not close because there is a large tube going through the window with tape around it. On a chilly day/night this is not comfortable and there is nothing one can do since the window does not close. You can also hear everything going on outside because the window does not close. Bedsheets were not clean either. Contacted the host about the window and bedsheets and the host gave me the...
United States
Noel
$204 nightly
The price is $204
Nov 4 - Nov 5
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
1 bedroom, WiFi, bed sheets
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
2.0 star property
9.0 out of 10, Wonderful, (2)
"Outstanding location and room. Please recheck the structure of the outdoor stairs. There are no support pullers from the top landing to the ground level. They’re attached directly to the home but has gaps by the windows. The stares are very slippery when wet and the arm rails are below waist level. Unfinished wood rails make splinters a thing. Super clean, quiet and relaxing. Would reserve again if we come back to the area. Thank you so much for all the support. "
United States
Pat D.
$115 nightly
The price is $129
Nov 4 - Nov 5
Total with taxes and fees
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Waterfront Cottage in Branford
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (97)
"Host was wonderful to work with. House is amazing. Very spacious, beds were 5 Star hotel worthy!The location and view were spectacular. This was a perfect location and checked off ALL the boxes. "
United States
Kelly C.
Waterfront Cottage in Branford
Dining
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
10.0 out of 10, Exceptional, (71)
"Great family get together where we all were very comfortable. "
United States
Leanne B.
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Interior
Stunning Apt W/ Parking and Gym | Downtown at Yale
Stunning Apt W/ Parking and Gym | Downtown at Yale
10.0 out of 10, Exceptional, (46)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
United Kingdom
Coco N.
Stunning Apt W/ Parking and Gym | Downtown at Yale
Property grounds
Cozy dog friendly updated house in quiet village adjacent to park
Cozy dog friendly updated house in quiet village adjacent to park
10.0 out of 10, Exceptional, (43)
"Very nice stay! Yard is beautiful!"
United States
Marilee P.
Cozy dog friendly updated house in quiet village adjacent to park
Dining
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
$1,045 nightly
The price is $1,182
Nov 27 - Nov 28
Total with taxes and fees
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Fridge, microwave, oven, dishwasher
Large Charming Historic House close to Beaches
Large Charming Historic House close to Beaches
9.8 out of 10, Exceptional, (33)
"We came down for a golf tournament and thoroughly enjoyed our stay. The house had plenty of room for all of us. A great beach close by."
United States
Marcia L.
Large Charming Historic House close to Beaches
Interior
Conference Room Rental no sleeping arrangements
Conference Room Rental no sleeping arrangements
$814 nightly
The price is $922
Nov 4 - Nov 5
Total with taxes and fees
Conference Room Rental no sleeping arrangements
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (7)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
United States
Lara S.
$217 nightly
The price is $245
Nov 4 - Nov 5
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

10/10 Excellent
"Brian, front of house, kind and excellent communicator!"
Linda 2-night trip
Posted 18 hours ago
Home2 Suites by Hilton East Haven New Haven

Find out more about Madison

Everything you need to know about Madison vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madison vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madison vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Madison in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Madison rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madison vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madison. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Waterfront Estate Home - Beach and Shared Pool - East: This highly rated vacation home rental in Madison is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Madison?

With 33 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 North Madison Shopping Center 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.