A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.

Madison Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Madison vacation rentals

A beach with a house in the background, a clear sky, and a calm sea.

1. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
$293 nightly
The price is $335
Nov 8 - Nov 9
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (66 reviews)
"We enjoyed our stay"
United States
JM B.
$206 nightly
The price is $235
Nov 9 - Nov 10
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

3. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (31 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
$300 nightly
The price is $341
Nov 5 - Nov 6
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
A glass enclosure with a view of a forest interior, including a bed and a small table with items.

4. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (216 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
$189 nightly
The price is $217
Nov 30 - Dec 1
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a granite island, stainless steel appliances, and a bar area with bar stools.

5. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (4 reviews)
"Very lovely home! We very much enjoyed our stay and hope to be back again!"
United States
Morgan M.
$486 nightly
The price is $556
Nov 10 - Nov 11
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
A modern living room with a large TV, white cabinetry, and a view of the outdoors.

6. Charming beach home, complete with pool & cozy guest house!

Charming beach home, complete with pool & cozy guest house!
Clinton
9.8 out of 10, Exceptional, (56 reviews)
"Beautiful, open and clean. Perfect for a family stay!"
United States
Juliana A.
$1,141 nightly
The price is $1,306
Nov 12 - Nov 13
Total with taxes and fees
Charming beach home, complete with pool & cozy guest house!
A hotel room with two beds, a desk, and a chair.

7. Spacious 2 Full Beds Nsmk

Spacious 2 Full Beds Nsmk
Branford
10.0 out of 10, Exceptional, (52 reviews)
"Really appreciated the clean, spacious feel throughout my stay."
United States
Anonymous traveler
$79 nightly
The price is $91
Dec 1 - Dec 2
Total with taxes and fees
Spacious 2 Full Beds Nsmk
A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

8. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.4 out of 10, Exceptional, (93 reviews)
"This is a great location, walking distance to the green and other sites. It also worked well for our girls trip of 4 women."
United States
Liz H.
$518 nightly
The price is $593
Nov 5 - Nov 6
Total with taxes and fees
Historic New England home ,Reunions Beach pass
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

9. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
$497 nightly
The price is $566
Nov 5 - Nov 6
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
A balcony with a view of the ocean, a lawn, and a house in the background.

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
$269 nightly
The price is $307
Nov 30 - Dec 1
Total with taxes and fees
Cliffside Resort Condominiums
A large, white, multi-story building with a prominent tower and a flag on top.

11. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveler
$239 nightly
The price is $272
Nov 9 - Nov 10
Total with taxes and fees
Walk To Goodspeed Opera House!
A modern house with a deck, outdoor seating, and a fire pit.

12. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (72 reviews)
"Everything was perfect 💞"
United States
Altynai
$296 nightly
The price is $338
Nov 8 - Nov 9
Total with taxes and fees
North Fork Resort
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

13. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
$482 nightly
The price is $549
Nov 16 - Nov 17
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

14. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (40 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
$221 nightly
The price is $252
Dec 1 - Dec 2
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A living room with a dark grey sofa, a wooden coffee table with a vase of white flowers, a patterned rug, and a ceiling fan.

15. Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (12 reviews)
"Property was clean and had all amenities we needed. Easy check in and check out"
United States
Sarah S.
$140 nightly
The price is $160
Nov 8 - Nov 9
Total with taxes and fees
Cozy East Haven Home • Near Beach & Yale
A two-story house with a covered porch, a front door, and a small outdoor seating area with a table and chairs.

16. Cozy Home near private beach , close to New Haven area colleges Hospitals

Cozy Home near private beach , close to New Haven area colleges Hospitals
Branford
9.4 out of 10, Exceptional, (86 reviews)
"Property was clean with some nice cozy touches. Wine on the table, fruit in the frig, chocolate for comfort, coffee for wakeup. Host was very pleasant and accommodating. Will definitely stay there again."
United States
Vincent
$254 nightly
The price is $289
Nov 17 - Nov 18
Total with taxes and fees
Cozy Home near private beach , close to New Haven area colleges Hospitals
A hotel room with a bed, bedside table with a phone, a desk with a chair, a TV, and a door leading to another room.

17. Cozy 1 King Bed | Smoking

Cozy 1 King Bed | Smoking
Branford
10.0 out of 10, Exceptional, (55 reviews)
"Before morning travel, we got much-needed rest here. Rooms had ample space so it didn't feel cramped at all, plus friendly staff shared helpful breakfast recommendations as part of our group treat experience."
United States
Anonymous traveler
$79 nightly
The price is $91
Dec 1 - Dec 2
Total with taxes and fees
Cozy 1 King Bed | Smoking
A hotel lobby with a reception desk, a television mounted on the wall, a small seating area with chairs, and a window providing a view outside.

18. Cozy 2 Full Beds|Free Parking & Wifi

Cozy 2 Full Beds|Free Parking & Wifi
Niantic
10.0 out of 10, Exceptional, (55 reviews)
"Close to local spots, good value for what you get."
United States
Anonymous traveler
$81 nightly
The price is $93
Nov 5 - Nov 6
Total with taxes and fees
Cozy 2 Full Beds|Free Parking & Wifi
A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

19. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
9.6 out of 10, Exceptional, (4 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
$282 nightly
The price is $322
Nov 6 - Nov 7
Total with taxes and fees
2BR Apartment Near Wesleyan 301
A modern hotel room with a bed, bedside table, chair, desk, and a television.

20. 1 King Bed | Nsmk, Micfridge

1 King Bed | Nsmk, Micfridge
Branford
10.0 out of 10, Exceptional, (52 reviews)
"The location is convenient with easy access to local shops and restaurants nearby."
United States
Anonymous traveler
$83 nightly
The price is $95
Dec 1 - Dec 2
Total with taxes and fees
1 King Bed | Nsmk, Micfridge
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

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"It was a good location. Would be nice to have coffee for guest in the morning - no one really likes to make it in the room."
Alycia and or Mike 1-night trip
Posted 11 hours ago
Hotel Marcel New Haven, Tapestry Collection By Hilton

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 $217 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?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This highly rated vacation home rental in Madison is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Madison is Waterfront Estate Home - Pool and Private Beach Pavilion - East.

How many vacation rentals are there in Madison?

With 36 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?

Hammonasset Beach and Meigs Point Nature Center 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 Scranton Memorial Library 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.