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

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
The price is CA $221
CA $513 total
includes taxes & fees
Jul 20 - Jul 21
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $206
CA $374 total
includes taxes & fees
Jul 21 - Jul 22
1-bedroom cottage with Grove Beach 🏖️ access.

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, (166 reviews)
"Great experience at usual."
United States
Andrea
The price is CA $189
CA $282 total
includes taxes & fees
Aug 17 - Aug 18
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is CA $232
CA $572 total
includes taxes & fees
Jul 20 - Jul 21
Adorable Cottage, 5 min walk to water & town

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, (7 reviews)
"Great host and property"
United States
Kevin K.
The price is CA $542
CA $973 total
includes taxes & fees
Aug 1 - Aug 2
Adorable Cottage with Cottage porch, walk to water & town

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.
The price is CA $421
CA $906 total
includes taxes & fees
Jul 22 - Jul 23
Historic New England home ,Reunions Beach pass

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, (33 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.
The price is CA $205
CA $396 total
includes taxes & fees
Aug 17 - Aug 18
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (32 reviews)
"Great stay & great staff!"
United States
James
The price is CA $528
CA $604 total
includes taxes & fees
Jul 20 - Jul 21
North Fork Resort

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.
The price is CA $273
CA $443 total
includes taxes & fees
Aug 3 - Aug 4
Walk To Goodspeed Opera House!

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
The price is CA $213
CA $404 total
includes taxes & fees
Jul 19 - Jul 20
The Stern at Soundview · Beach+Ocean+Sunrise

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (272 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is CA $437
CA $560 total
includes taxes & fees
Jul 23 - Jul 24
Cliffside Resort Condominiums

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (9 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
United States
Cheryl H.
The price is CA $213
CA $683 total
includes taxes & fees
Jul 20 - Jul 21
Rogers Lake House (87) · CT College+Beach+USCGA

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Clinton
10.0 out of 10, Exceptional, (30 reviews)
"It was a very clean well kept property. The accommodation was very comfortable. We all truly enjoyed the house and location. "
United States
claire
The price is CA $1,483
CA $2,460 total
includes taxes & fees
Jul 31 - Aug 1
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

Prime Yale Studio Steps to Sallys Apizza

Prime Yale Studio Steps to Sallys Apizza
Downtown New Haven
The price is CA $114
CA $303 total
includes taxes & fees
Jul 20 - Jul 21
Prime Yale Studio Steps to Sallys Apizza

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.
The price is CA $89
CA $235 total
includes taxes & fees
Jul 20 - Jul 21
One bedroom in United States of America, New Haven

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, (139 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is CA $554
CA $988 total
includes taxes & fees
Jul 19 - Jul 20
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

adorable ranch in beach community

adorable ranch in beach community
Old Saybrook
10.0 out of 10, Exceptional, (45 reviews)
"The experience was a pleasure - the house is comfy, and the location amazing! "
United States
Matthew V.
The price is CA $701
CA $1,179 total
includes taxes & fees
Jul 19 - Jul 20
adorable ranch in beach community

Hollow Brook Estate

Hollow Brook Estate
Killingworth
10.0 out of 10, Exceptional, (2 reviews)
"Large property with multiple entertaining spaces in a peaceful and secluded setting."
United States
Thomas D.
The price is CA $2,797
CA $4,521 total
includes taxes & fees
Aug 7 - Aug 8
Hollow Brook Estate

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (49 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is CA $508
CA $929 total
includes taxes & fees
Jul 22 - Jul 23
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

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.
The price is CA $165
CA $408 total
includes taxes & fees
Aug 1 - Aug 2
Once the old Schools house now a newly furnished Apartment
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.

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?

Hammonasset Beach and East Wharf Beach Park 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 Meigs Point Nature 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.