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Top Holiday Rentals in Madison

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

10.0 out of 10, Exceptional, (62)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (226)
"Very nice, clean and cosy place! Highly recommend!"
The price is £484
includes taxes & fees
28 Jul - 29 Jul
Cliffside Resort Condominiums

Postcard Cabins Machimoodus

2.0 star property
9.8 out of 10, Exceptional, (32)
"Great stay"
The price is £198
includes taxes & fees
13 Jul - 14 Jul
Postcard Cabins Machimoodus

Rustic Lakeside Cabin at White Gate Farm

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

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 £152
includes taxes & fees
16 Jul - 17 Jul
The Stern at Soundview · Beach+Ocean+Sunrise

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

10.0 out of 10, Exceptional, (133)
"My husband and I had a wonderful time at this idyllic cottage on the water in Branford. Great location and hosts. Beautiful community for long walks, restaurants nearby. Highly recommend! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is £197
includes taxes & fees
15 Jul - 16 Jul
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 £189
includes taxes & fees
23 Jul - 24 Jul
Freeboard at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is £153
includes taxes & fees
17 Jul - 18 Jul
The Anchor 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 £486
includes taxes & fees
2 Aug - 3 Aug
adorable ranch in beach community

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

10.0 out of 10, Exceptional, (34)
"My wife and I loved our weekend stay at this cabin!"
The price is £564
includes taxes & fees
13 Jul - 14 Jul
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 £168
includes taxes & fees
14 Jul - 15 Jul
The Mast at Soundview · Beach+Ocean+Sunrise

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

10.0 out of 10, Exceptional, (39)
"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

Sweet Cottage in Beach Community

10.0 out of 10, Exceptional, (7)
"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 .

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

2.0 star property
8.4 out of 10, Very good, (5)
"Beautiful location, very comfortable for our small family."
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
10.0 out of 10, Exceptional, (1)
"Everything was great!"
The price is £326
includes taxes & fees
15 Jul - 16 Jul
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach

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
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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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 34 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.