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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Our top choices for Madison vacation rentals

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.
The price is CA $211
CA $501 total
includes taxes & fees
Oct 20 - Oct 21
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

2. 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, (30 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is CA $223
CA $426 total
includes taxes & fees
Oct 19 - Oct 20
The gardners Cottage 1 mile from long Island Sound - pet friendly

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (63 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $146
CA $295 total
includes taxes & fees
Oct 21 - Oct 22
1-bedroom cottage with Grove Beach 🏖️ access.

4. 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.
The price is CA $957
CA $1,996 total
includes taxes & fees
Nov 12 - Nov 13
Charming beach home, complete with pool & cozy guest house!

5. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.2 out of 10, Wonderful, (91 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.
The price is CA $424
CA $914 total
includes taxes & fees
Oct 27 - Oct 28
Historic New England home ,Reunions Beach pass

6. 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, (204 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is CA $180
CA $272 total
includes taxes & fees
Nov 16 - Nov 17
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is CA $239
CA $430 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums

8. 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.
The price is CA $407
CA $793 total
includes taxes & fees
Oct 21 - Oct 22
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

9. 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.
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

10. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (66 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is CA $414
CA $473 total
includes taxes & fees
Oct 19 - Oct 20
North Fork Resort

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 traveller
The price is CA $197
CA $341 total
includes taxes & fees
Nov 9 - Nov 10
Walk To Goodspeed Opera House!

12. 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, (39 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.
The price is CA $177
CA $376 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

13. 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 traveller
The price is CA $115
CA $132 total
includes taxes & fees
Nov 1 - Nov 2
Cozy 1 King Bed | Smoking

14. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable with easy communication with host I recommend this unit to all who want to visit Wallingford or who desire to take the train to ny or Boston etc"
United States
DAVID B.
The price is CA $170
CA $417 total
includes taxes & fees
Oct 20 - Oct 21
All New Studio apartment in center of town

15. 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, (83 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
The price is CA $155
CA $430 total
includes taxes & fees
Oct 21 - Oct 22
Cozy Home near private beach , close to New Haven area colleges Hospitals

16. 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.
The price is CA $209
CA $270 total
includes taxes & fees
Oct 20 - Oct 21
Cozy East Haven Home • Near Beach & Yale

17. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
10.0 out of 10, Exceptional, (34 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is CA $919
CA $1,553 total
includes taxes & fees
Oct 19 - Oct 20
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

18. 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, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is CA $170
CA $421 total
includes taxes & fees
Oct 19 - Oct 20
Once the old Schools house now a newly furnished Apartment

19. Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (14 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
Clear LI Sound waterview, Wedding pics, Yale&Beach
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

Find out more about Madison

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Madison. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.