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

Madison Vacation Rentals

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!
Coffee/tea maker, fridge, microwave, oven

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, (25 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$288 nightly
The price is $326
Sep 2 - Sep 3
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
View from property

3. 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, (175 reviews)
"Beautiful view, very clean !"
United States
Karolyne
$239 nightly
The price is $275
Aug 6 - Aug 7
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Condo | Terrace/patio

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (280 reviews)
"Great place!"
United States
Christine
$452 nightly
The price is $516
Aug 6 - Aug 7
Total with taxes and fees
Cliffside Resort Condominiums
1 bedroom, desk, iron/ironing board, travel crib

5. 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.
$216 nightly
The price is $245
Sep 2 - Sep 3
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Flat-screen TV

6. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (44 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$612 nightly
The price is $699
Aug 10 - Aug 11
Total with taxes and fees
North Fork Resort
Terrace/patio

7. 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.
$2,622 nightly
The price is $2,966
Aug 7 - Aug 8
Total with taxes and fees
Hollow Brook Estate
Terrace/patio

8. 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.
$564 nightly
The price is $639
Sep 2 - Sep 3
Total with taxes and fees
Historic New England home ,Reunions Beach pass
Interior

9. 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.
$403 nightly
The price is $457
Aug 9 - Aug 10
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Interior

10. 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)
"The house was great for our group of 8. The lister's were very helpful and gracious when one of our members left their wallet behind. We had a lovely time and recommend the property."
United States
Stephanie G.
$589 nightly
The price is $666
Aug 6 - Aug 7
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
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.
$247 nightly
The price is $280
Sep 1 - Sep 2
Total with taxes and fees
Walk To Goodspeed Opera House!
Smart TV, books

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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (10 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.
$852 nightly
The price is $961
Aug 23 - Aug 24
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Dining

13. Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Old Saybrook
9.8 out of 10, Exceptional, (40 reviews)
"Enjoyed our stay"
United States
Nicole L.
$1,598 nightly
The price is $1,808
Aug 16 - Aug 17
Total with taxes and fees
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Beach nearby

14. 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
$262 nightly
The price is $296
Aug 6 - Aug 7
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Exterior

15. 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, (50 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
$770 nightly
The price is $872
Aug 25 - Aug 26
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Interior

16. 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
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful house in a great location."
United States
Edward S.
$909 nightly
The price is $1,029
Aug 9 - Aug 10
Total with taxes and fees
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
House (3 Bedrooms) | Interior

17. Lakefront Home, Close to Mt Southington!

Lakefront Home, Close to Mt Southington!
3.0 star property
Wolcott
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house with great views of the lake. "
United States
Darrell
Lakefront Home, Close to Mt Southington!
Terrace/patio

18. Oceanfront Couples Retreat - Pvt Beach + Firepit

Oceanfront Couples Retreat - Pvt Beach + Firepit
Morgan Point
9.8 out of 10, Exceptional, (16 reviews)
"Gorgeous location on LI sound! The home was perfect for us. We had plenty of room to spread out and we relax. We enjoyed the deck and the bar area! We all slept very well and we actually loved watching the planes overhead! Lots of fun spots nearby to explore and are already hoping to come back in the fall. "
United States
Carrie R.
$923 nightly
The price is $1,046
Aug 7 - Aug 8
Total with taxes and fees
Oceanfront Couples Retreat - Pvt Beach + Firepit
Exterior

19. Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
East Rock
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
Australia
Nina
$476 nightly
The price is $537
Sep 2 - Sep 3
Total with taxes and fees
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
Smart TV, books

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

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (13 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
$590 nightly
The price is $668
Aug 23 - Aug 24
Total with taxes and fees
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"Very clean room, some hidden costs added during check in. Resort fee tax and town or state"
Jan 1-night trip
Posted 1 day ago
Water's Edge Resort & Spa

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 34 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 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.