Madison Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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.
$245 nightly
The price is $280
Nov 15 - Nov 16
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)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
$200 nightly
The price is $229
Nov 10 - Nov 11
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.
$291 nightly
The price is $332
Nov 10 - Nov 11
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

4. 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.
$512 nightly
The price is $585
Dec 1 - Dec 2
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
A cabin with a dining table set for two, a bicycle, and a small porch area.

5. 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, (222 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
$167 nightly
The price is $192
Dec 9 - Dec 10
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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.
$1,162 nightly
The price is $1,327
Nov 12 - Nov 13
Total with taxes and fees
Charming beach home, complete with pool & cozy guest house!
A reception desk with a staff member, a guest, and a child.

7. 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 $90
Dec 1 - Dec 2
Total with taxes and fees
Cozy 1 King Bed | Smoking
A balcony with a view of the ocean, a lawn, and a house in the background.

8. 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 covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

9. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.4 out of 10, Exceptional, (93 reviews)
"The location of this place is best!"
United States
Dr. Maureen C.
$524 nightly
The price is $599
Nov 10 - Nov 11
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.

10. 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.
$485 nightly
The price is $554
Nov 10 - Nov 11
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
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
$194 nightly
The price is $222
Dec 7 - Dec 8
Total with taxes and fees
Walk To Goodspeed Opera House!
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

12. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (15 reviews)
"Cute little house with excellent amenities. Perfect for our cousins getaway!"
United States
Karol T.
$607 nightly
The price is $694
Nov 20 - Nov 21
Total with taxes and fees
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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.
$468 nightly
The price is $535
Nov 16 - Nov 17
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A modern house with a deck, outdoor seating, and a fire pit.

14. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
$299 nightly
The price is $341
Nov 15 - Nov 16
Total with taxes and fees
North Fork Resort
A hotel room with two beds, a desk, and a chair.

15. 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 $90
Dec 1 - Dec 2
Total with taxes and fees
Spacious 2 Full Beds Nsmk
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.

16. 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.
$216 nightly
The price is $247
Nov 16 - Nov 17
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A hotel reception desk with a staff member, a guest, and a child.

17. MS6 Branford | 1 King Bed Smk, Micfridge

MS6 Branford | 1 King Bed Smk, Micfridge
Branford
10.0 out of 10, Exceptional, (50 reviews)
"Those beds were very large and super cozy!"
United States
Anonymous traveler
$82 nightly
The price is $95
Dec 1 - Dec 2
Total with taxes and fees
MS6 Branford | 1 King Bed Smk, Micfridge
A reception desk with a staff member, a guest, and a child.

18. Cozy 1 King Bed | Non-Smoking

Cozy 1 King Bed | Non-Smoking
Branford
10.0 out of 10, Exceptional, (55 reviews)
"Stayed one night, quick checkout process got me back on road promptly!"
United States
Anonymous traveler
$79 nightly
The price is $90
Dec 1 - Dec 2
Total with taxes and fees
Cozy 1 King Bed | Non-Smoking
A reception desk with a staff member, a guest, and a child.

19. 1 King Bed | Mob Acc Tub, Nsmk

1 King Bed | Mob Acc Tub, Nsmk
Branford
10.0 out of 10, Exceptional, (51 reviews)
"Quiet evenings with an easy check-in process made this place worth returning to if passing by again soon."
United States
Anonymous traveler
$80 nightly
The price is $91
Dec 1 - Dec 2
Total with taxes and fees
1 King Bed | Mob Acc Tub, Nsmk
A reception desk with a staff member, a guest, and a child.

20. Cozy 2 Full Beds Micfridge Parking

Cozy 2 Full Beds Micfridge Parking
Branford
10.0 out of 10, Exceptional, (50 reviews)
"The rooms offered a quiet space that was perfect for resting."
United States
Anonymous traveler
$81 nightly
The price is $94
Dec 1 - Dec 2
Total with taxes and fees
Cozy 2 Full Beds Micfridge Parking
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

A red door with a 'Gone to the Beach' sign, a wicker chair, a table with a plate of food and drinks, and a potted plant.
The Homestead

The Homestead

The Homestead
Madison Center

10/10 Excellent

Breakfast should be more robust off season. Hefty price just for a room
United States
Mitchell
Reviewed February 12, 2023
The Homestead

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 $90 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.

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.

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