House holiday rentals in Madison

Spacious 5 BR Home near town

Spacious 5 Bedroom 2 story farmhouse in quiet neighborhood of Historic Guilford. Perfect for family gatherings, reunions, special occasions, traveling work crews, or a simple vacation getaway. There is ample room for everyone to relax and unwind. The kitchen is stocked with enough dinnerware and appliances for all Just 1 mile from town, the home offers easy access to I-95, New Haven, Yale Univ. and the scenic Connecticut shoreline. Hiking trails & local PYO Farm Market are a short walk away.

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Perfect Cape Beach Cottage in Madison CT!

Come enjoy your perfectly quintessential New England vacation in this beautiful beach cottage in Madison, Conncecticut - modern, luxe, and pull-at-your-heart-strings-endearing, your worries will melt away in this peaceful property. DEEDED BEACH ACCESS TO PRIVATE NEIGHBORHOOD SANDY BEACH - pics of the beach included. Note that bedrooms are located at the top of a (one-story) spiral staircase - if anyone in your party has mobility issues or questions on access, please contact host for inputs.

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Extremely comfortable house with amazing views in a peaceful neighborhood. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, music, and lots more.

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Stylish Modern Home, 4-Bedroom, Madison CT

Beautiful 4-Bedroom Residential Home in Madison, Connecticut - Contemporary Scandinavian Interior Design - Close to Local/State Beaches (~10 Minute Drive) - Close to Local Parks and Hiking Areas (~3 Minute Drive) - Welcoming Open Floorplan - Quality Furnishings and Finishes - Up-to-Date/Modern Features/Clean and Comfortable - Wonderful Garden and Grass Lawn - Private (House Sits on 2-Acre Parcel) - Enclosed Outdoor Shower - Surrounded by Natural Beauty of the Countryside

Oceanfront Beach House w/ Private Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

INSTANT BOOK: Mid May 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Treasured 1924 Colonial "Sweet Caroline"

"Sweet Caroline" is a charming 4 bedroom shoreline colonial that has been recently renovated to provide an up-to-date feel while maintaining it's 1920's charm. We fell in love with this home last summer while visiting friends and family and decided to make it our home away from home. We have enjoyed her so much that we decided to share her with others seeking similar cozy, New England shoreline, accommodations.