Holiday houses in Trumbull

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Cozy, updated single family in Fairfield County

Welcome to your home away from home! Thoughtfully furnished with comfort, style, and convenience, this cozy retreat is perfectly situated for your next Fairfield County visit. Located just one minute from SHU and the Merritt Parkway, you're ideally placed to explore local parks, beaches, shopping, and delicious restaurants. Having personally enjoyed living here, we've crafted a welcoming space with special touches that we’re excited to share with you. Relax, settle in, and feel right at home!

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

The Elijah Sterling House

Enjoy your visit to Trumbull in this spacious, family friendly, and historic home, circa 1791. Trumbull has restaurants, shopping, and hiking trails. Just a short drive to state parks & beaches. Total Mortgage Arena, the Bridgeport Amphitheater, Fairfield U, SHU, and University of Bridgeport conveniently located. Close to all highways. Visiting NYC? Take the train at the Fairfield Metro station, with convenient & reasonable parking. This historic home is delightful, and we welcome you!

Charming 1-Bedroom duplex apartment in Monroe

Welcome to Your Home Away from Home! Escape to our cozy 1-bedroom apartment nestled in a private setting in Monroe. Perfect for couples, solo travelers, or small families, this tranquil retreat offers all the comforts you need for a relaxing stay: Spacious Bedroom, Fully Equipped Kitchen, Private Entrance, Outdoor Area, Free Wi-Fi. Situated in a quiet neighborhood, our apartment is just a short drive from local attractions, Trumbull Mall, parks, restaurants and nearby hiking trails.

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Top Rated Gem | Fire Pit | BBQ | FFU | Near Beach

Welcome to Fairfield Cottage, a cozy retreat that beautifully combines comfort and stylish design for you and your guests. With thoughtful decor and essential amenities, you'll feel right at home. Conveniently located just 90 minutes to NYC, you can easily visit attractions like the Norwalk Aquarium, Beardsley Zoo, and local farms. Unwind at nearby Jennings and Penfield beaches located just 3 miles away, or explore the charming village of Southport.

New & Modern Studio Apartment in Fairfield

This newly reconstructed downstairs stylish, modern, and spacious studio features a queen bed and a queen pull-out sofabed, luxe bathroom including towels and washcloths, sleek kitchen, a 70” TV with surround sound etc. Enjoy a private garden entrance, in-suite laundry, guest-controlled heat, and ceiling fan. Close to Fairfield & Sacred Heart Universities, shops, beach, and quick NYC transit. Comfort and convenience in one chic space!

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.