Holiday Rentals in Madison

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Holiday Rentals in Madison

Waterfront Estate Home - Beach and Shared Pool - East

9.8 out of 10, Exceptional, (43)
"Perfect home for a big family gathering!"
Waterfront Estate Home - Beach and Shared Pool - East

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (64)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (44)
"Great stay"
The price is €173
includes taxes & fees
4 Aug - 5 Aug
Postcard Cabins Machimoodus

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (231)
"Great property overall with beautiful grounds, a pool and access to the beach. Condos are spacious and equipped with bathroom and kitchen items. Ours had a patio with a great view of the water! We will definitely stay here again. "
The price is €258
includes taxes & fees
4 Aug - 5 Aug
Cliffside Resort Condominiums

NORTHFORK COTTAGE with POOL & HOT TUB

4.0 star property
9.6 out of 10, Exceptional, (133)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (2)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is €193
includes taxes & fees
27 Aug - 28 Aug
The Stern at Soundview · Beach+Ocean+Sunrise

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (136)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

The Anchor at Soundview · Beach+Ocean+Sunrise

2.0 star property
8.0 out of 10, Very good, (1)
"Great stay. Clean, all amenities provided, located short walk from beach. I wouldn’t call it an apartment or studio, though. It’s the size of a bedroom and includes only a bed, dresser, fridge and microwave. Not even a chair. Description made me expect a bit more but if you know the size going in, it’s a marvelous place to stay. "
The price is €174
includes taxes & fees
19 Aug - 20 Aug
The Anchor at Soundview · Beach+Ocean+Sunrise

COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

10.0 out of 10, Exceptional, (38)
"My wife and I loved our weekend stay at this cabin!"
The price is €575
includes taxes & fees
24 Aug - 25 Aug
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

Shoreline Oasis

8.8 out of 10, Excellent, (5)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is €230
includes taxes & fees
5 Aug - 6 Aug
Shoreline Oasis

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (28)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is €227
includes taxes & fees
1 Sept - 2 Sept
1-bedroom cottage with Grove Beach 🏖️ access.

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (112)
"Just amazing!"
Rustic Lakeside Cabin at White Gate Farm

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is €566
includes taxes & fees
13 Aug - 14 Aug
adorable ranch in beach community

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
8.8 out of 10, Excellent, (3)
"I love everything about this property. Excellent response from host. Excellent cleanliness of place. OVERALL TOP EXPERIENCE. 1000 PERCENT will be back."
The price is €168
includes taxes & fees
5 Aug - 6 Aug
Freeboard at Soundview · Beach+Ocean+Sunrise

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Charming Farm Abode with gourmet food and access to lake, trails & farm fun

10.0 out of 10, Exceptional, (42)
"We stayed one night and not only was the property clean and adorable, but the staff were lovely and the farmer’s market was amazing!"
The price is €504
includes taxes & fees
24 Aug - 25 Aug
Charming Farm Abode with gourmet food and access to lake, trails & farm fun

Cozy 3 bedroom minutes from Yale and the beach

7.0 out of 10, Good, (2)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.0 out of 10, Wonderful, (2)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
The price is €188
includes taxes & fees
3 Sept - 4 Sept
The Mast at Soundview · Beach+Ocean+Sunrise

Vintage Cottage by the Sea - Walking Distance to the Beach - Old Lyme

6.0 out of 10, (1)
"Overall we were happy with our stay, but that had more to do with the location than the house. I would have liked the check in details slightly earlier because we were traveling from a couple hours away and I was nervous we would not be able to get into the house. When I booked it said we would receive check in details a few days in advance. When we arrived there were some piles of dirt, leaves and sticks on the floor. The house did not have a broom, vacuum or dust pan. In addition to the piles...
Vintage Cottage by the Sea - Walking Distance to the Beach - Old Lyme

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (91)
"It was a very nice stay. Sound of the ocean was calming. We would go back. "
Waterfront House with picture-perfect views from all 3 levels.
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

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals in Madison close to RJ Julia Booksellers, or you can select a more secluded 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 holiday rentals that Madison has to offer?

Waterfront Estate Home - Beach and Shared Pool - East: This highly rated holiday home rental in Madison is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Madison?

With 33 Expedia holiday rentals, you're guaranteed to find just the right place for your Madison stay.

What’s there to see and do in Madison?

Family-friendly attractions include RJ Julia Booksellers and Anna Mia's, whereas Hammonasset Beach and Meigs Point Nature Center are a couple of great spots to enjoy the outdoors. Hammonasset Beach State Park and North Madison Shopping Center are other places to visit while you're in town.

What’s a holiday rental in Madison like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madison. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.