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

Madison Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Madison vacation rentals

Sun loungers, beach towels

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
$322 nightly
The price is $364
Aug 24 - Aug 25
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
1 bedroom, desk, iron/ironing board, travel crib

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay"
United States
JM B.
$192 nightly
The price is $218
Sep 9 - Sep 10
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Coffee/tea maker, fridge, microwave, oven

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, (25 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$288 nightly
The price is $326
Sep 1 - Sep 2
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
View from property

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, (176 reviews)
"Beautiful view, very clean !"
United States
Karolyne
$224 nightly
The price is $258
Sep 8 - Sep 9
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Property grounds

5. NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The house has a cozy, homey feel and was a nice place to come back to after being out for the day. It was quiet, comfortable, and had a relaxed vibe that made the trip easy.The location was a big plus for us. Hammonasset Beach was only a few minutes away, and Madison center was just as close, which made it easy to grab dinner or pop out for anything we needed. The outdoor fireplace was also a really nice touch and made the evenings feel special.Overall, it was a...
United States
Moe B.
$557 nightly
The price is $631
Aug 16 - Aug 17
Total with taxes and fees
NEW Coastal Cottage 2 Miles to Beach + Lake Access
Interior

6. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (16 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
$397 nightly
The price is $449
Aug 11 - Aug 12
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Terrace/patio

7. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.2 out of 10, Wonderful, (90 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.
$511 nightly
The price is $579
Aug 10 - Aug 11
Total with taxes and fees
Historic New England home ,Reunions Beach pass
Living area

8. Cozy 1-bedroom apartment in peaceful Branford with AC and gym access

Cozy 1-bedroom apartment in peaceful Branford with AC and gym access
Branford
$156 nightly
The price is $177
Sep 8 - Sep 9
Total with taxes and fees
Cozy 1-bedroom apartment in peaceful Branford with AC and gym access
Smart TV, fireplace, books, music library

9. 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, (34 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
$225 nightly
The price is $255
Aug 24 - Aug 25
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Dining

10. Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Westbrook Center
9.4 out of 10, Exceptional, (3 reviews)
"We had a lovely time during our stay. The hosts were excellent with communication and quick responses throughout our stay. The 2 family suites were perfect for our families to all stay together during this trip. We would definitely book again! "
United States
Kate G.
$735 nightly
The price is $832
Aug 11 - Aug 12
Total with taxes and fees
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Exterior

11. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (40 reviews)
"Simple process, plenty of room, ample parking and no issues with noise from the business above. "
United States
Amber J.
$257 nightly
The price is $291
Aug 12 - Aug 13
Total with taxes and fees
Walk To Goodspeed Opera House!
Interior

12. 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.
$583 nightly
The price is $660
Sep 8 - Sep 9
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Smart TV

13. Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (10 reviews)
"Easy check in and was as described. It was perfect for our needs for a place to stay over the holidays."
United States
Danielle D.
$296 nightly
The price is $335
Aug 29 - Aug 30
Total with taxes and fees
Cozy East Haven Home • Near Beach & Yale
Exterior

14. Prime Yale Studio Steps to Sallys Apizza

Prime Yale Studio Steps to Sallys Apizza
Downtown New Haven
$198 nightly
The price is $224
Aug 12 - Aug 13
Total with taxes and fees
Prime Yale Studio Steps to Sallys Apizza
Condo | Terrace/patio

15. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (281 reviews)
"Great place!"
United States
Christine
$385 nightly
The price is $439
Sep 9 - Sep 10
Total with taxes and fees
Cliffside Resort Condominiums
Beach nearby

16. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$268 nightly
The price is $303
Aug 10 - Aug 11
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
1 bedroom, desk, iron/ironing board, WiFi

17. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
$150 nightly
The price is $170
Aug 11 - Aug 12
Total with taxes and fees
One bedroom in United States of America, New Haven
Exterior

18. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$274 nightly
The price is $292
Aug 11 - Aug 12
Total with taxes and fees
All New 1BR with tons of Charm
1 bedroom, iron/ironing board, WiFi, bed sheets

19. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$274 nightly
The price is $292
Aug 13 - Aug 14
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Exterior

20. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (14 reviews)
"Conveniently located and nice, practically appointed stay for a business trip to work with a collaborator in town."
United States
Jeremy Y.
$216 nightly
The price is $245
Aug 10 - Aug 11
Total with taxes and fees
Bright Downtown Studio near Yale & East Rock!
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

New Haven Hotel

New Haven Hotel

8/10 Good
"The front desk staff was consistently friendly and helpful. The parking situation was ideal. It was all good!"
Janice 1-night trip
Posted 12 hours ago
New Haven Hotel

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 $137 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.

How many vacation rentals are there in Madison?

With 35 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 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.