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Top 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
9.4 out of 10, Exceptional, (45)
"Great stay"
The price is £158
includes taxes & fees
12 Aug - 13 Aug
Postcard Cabins Machimoodus

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (233)
"Great location, great views. Walls are a little thin."
The price is £349
includes taxes & fees
1 Sept - 2 Sept
Cliffside Resort Condominiums

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

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

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is £166
includes taxes & fees
27 Aug - 28 Aug
The Stern 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 £494
includes taxes & fees
13 Aug - 14 Aug
adorable ranch in beach community

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 £149
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, (39)
"My wife and I loved our weekend stay at this cabin!"
The price is £516
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 £199
includes taxes & fees
12 Aug - 13 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 £210
includes taxes & fees
19 Aug - 20 Aug
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

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 £144
includes taxes & fees
26 Aug - 27 Aug
Freeboard 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 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 £437
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

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

9.6 out of 10, Exceptional, (92)
"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.

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 £163
includes taxes & fees
3 Sept - 4 Sept
The Mast at Soundview · Beach+Ocean+Sunrise

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (48)
"We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!"
The price is £1,192
includes taxes & fees
4 Sept - 5 Sept
Work and Play Special! Extended Stay Discount
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 32 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.