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Compare 681 Vacation Homes in Madison with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (81)
"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.

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (23)
"This was the BEST decision for our family. The house was very cozy, old charm feel with some modern updates. The downstairs bathroom had a Spa vibe. We loved the 6 bedrooms & spacious kitchen & dining room. Loved how close it was to food & entertainment. The walk to the beach was only 10 minutes & very safe. We are use to blinds and/or shades, so just having light curtains for the windows was"
Large Charming Historic House close to Beaches

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (13)
"My college friends and I try to get away a few times a year and our latest weekend trip was to Westbrook. I love the Connecticut shore any time of year but off season is my favorite (very affordable hahaha). I was so happy when I walked into this house - sooooo clean, it had everything we needed in the kitchen, comfortable beds, and a very responsive host (thank you Wendy!). Even though it was March we were lucky enough to bundle up and enjoy coffee out on the patio! I can’t say enough about...
Cozy Westbrook Vacation Rental - Walk to Beach!

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

10.0 out of 10, Exceptional, (56)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Waterfront Beach House

9.6 out of 10, Exceptional, (42)
"The property is nicely located on the water and convenient to many attractions. "
Waterfront Beach House

Luxe Lake House in Connecticut

10.0 out of 10, Exceptional, (2)
"The house easily accommodated my friends and family for a weekend of relaxation. The place is very spacious with all modern amenities. We especially loved waking up to the gorgeous view of the lake in the back. The views were breathtaking. Would definitely consider going back. "
The price is SAR 1,316
SAR 3,392 total
includes taxes & fees
30 Mar - 31 Mar
Luxe Lake House in Connecticut

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (88)
"Everything was just fine - nothing spectacular but good enough for a short stay. Extremely safe feeling location"
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Beach House

9.8 out of 10, Exceptional, (50)
"Wonderful location. Cozy space we had a wonderful time"
Beach House

Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

10.0 out of 10, Exceptional, (55)
"Lovely, spacious and clean. We spent our Christmas holiday together with our family and the house was spacious and spotless. We had 5 adults with 2 small children in house. We hosted Christmas dinner for us and local family. Great space. Would love to rent in summer months to utilize outdoor space"
Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

Magic Place

The price is SAR 1,688
SAR 2,978 total
includes taxes & fees
23 Apr - 24 Apr
Magic Place

Waterfront Lakehouse in Clinton, CT with Hot Tub!

7.0 out of 10, Good, (2)
"My family and I absolutely loved our stay at this home! It was the perfect retreat for us, and we thoroughly enjoyed the hot tub and the breathtaking sunset views, especially while cooking in the beautifully designed kitchen. The kitchen was fully equipped, making it easy to prepare an amazing family dinner. The town of Clinton was absolutely charming, with the friendliest people, and we fell in love with Hammonasset Beach—it’s a must-visit! We’ll definitely be returning in the summer. The...
Waterfront Lakehouse in Clinton, CT with Hot Tub!

North Fork Family and Friends Getaway. Great Location

10.0 out of 10, Exceptional, (9)
"10 of us stayed at this house during LDW and had the most incredible experience. The pictures do not do the house justice- it was even better than we anticipated. Beyond gorgeous, so clean, huge, and the backyard will leave you speechless. We cannot recommend it enough. The only downside was the bedrooms upstairs were warm. Thank you to our amazing hosts!!!! We will be back. "
North Fork Family and Friends Getaway. Great Location

Grammy's Lake House w/ Private Waterfront Access

9.6 out of 10, Exceptional, (11)
"Enjoyable stay, nice property and great views. The home is aged, but the location is amazing! We had a nice weekend excursion to enjoy New England in October. "
Grammy's Lake House w/ Private Waterfront Access

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (42)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

10.0 out of 10, Exceptional, (7)
"It was a great house to host our family for Thanksgiving dinner! "
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

10.0 out of 10, Exceptional, (9)
"Is a great location given minutes from Yale. We were able to make a nice meal to celebrate our son’s success. Nice place!"
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (4)
"We came to the area for a long weekend event at Wesleyan University. I had never booked through VRBO and was not familiar with the process. From my first communication with Gilbert I felt like I was going to visit family. He was amazing to communicate with provided information about the area and the process and was super accommodating when he learned our flight was arriving early. From the moment we stepped through the door we knew our stay would be special. The home is beautiful, beds...
The price is SAR 469
SAR 837 total
includes taxes & fees
28 Apr - 29 Apr
Family Stays: Middletown, CT

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (116)
"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

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

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
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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Other property types in Madison

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

10.0 out of 10, Exceptional, (56)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2019)
"It was nice"
The price is SAR 341
SAR 392 total
includes taxes & fees
8 Apr - 9 Apr
New Haven Village Suites

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
The price is SAR 650
SAR 905 total
includes taxes & fees
13 Apr - 14 Apr
Cliffside Resort Condominiums
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.