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Madison Holiday Rentals

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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, (63)
"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, (41)
"Great stay"
The price is AU$342
includes taxes & fees
23 July - 24 July
Postcard Cabins Machimoodus

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (228)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is AU$656
includes taxes & fees
27 July - 28 July
Cliffside Resort Condominiums

NORTHFORK COTTAGE with POOL & HOT TUB

4.0 star property
9.8 out of 10, Exceptional, (130)
"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 AU$386
includes taxes & fees
19 Aug - 20 Aug
The Stern at Soundview · Beach+Ocean+Sunrise

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (110)
"Just amazing!"
Rustic Lakeside Cabin at White Gate Farm

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

10.0 out of 10, Exceptional, (135)
"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 AU$305
includes taxes & fees
30 July - 31 July
The Anchor at Soundview · Beach+Ocean+Sunrise

Shoreline Oasis

9.0 out of 10, Wonderful, (4)
"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 AU$408
includes taxes & fees
24 July - 25 July
Shoreline Oasis

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
"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 AU$294
includes taxes & fees
23 July - 24 July
Freeboard at Soundview · Beach+Ocean+Sunrise

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 AU$1,001
includes taxes & fees
2 Aug - 3 Aug
adorable ranch in beach community

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

10.0 out of 10, Exceptional, (40)
"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!"
Charming Farm Abode with gourmet food and access to lake, trails & farm fun

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

10.0 out of 10, Exceptional, (37)
"My wife and I loved our weekend stay at this cabin!"
The price is AU$1,083
includes taxes & fees
24 July - 25 July
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

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 AU$294
includes taxes & fees
23 July - 24 July
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

Sweet Cottage in Beach Community

10.0 out of 10, Exceptional, (8)
"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."
Sweet Cottage in Beach Community

'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 Westbrook Cottage, Steps to Private Beach

9.8 out of 10, Exceptional, (6)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach

The Rudder at Soundview · Beach+Ocean+Sunrise

The price is AU$301
includes taxes & fees
23 July - 24 July
The Rudder at Soundview · Beach+Ocean+Sunrise
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?

New Madison beach house - Ocean front- Great views- booking Summer 2025: This highly rated holiday home rental in Madison is located on the beach, and has a balcony, a BBQ 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 that you can cook with friends or family.

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.