Family-friendly holiday rentals in Trumbull

2 BRm Suite; Ktchn; Livng area; wash/dryr; Private

Fully accessorized, large (919 sq ft) beautiful suburban space with bedroom (queen); convertible Murphy bed (queen), in-room sitting area/large screen TV, kitchenette; 2nd room: bedroom (queen) with living space / large screen TV; private full bath; in-suite washer/dryer; private entry to suite (front door; up 1 flight of stairs). Includes light continental breakfast. Owners on property. Off street parking. Train station a mile away (NYC: 70 min). 2 miles to beach. Easy walk to Fairfield U.

Kitchen · Indoor spaces · Biking

3BR Cottage Walk to Beach and Tide Wedding Venue

Walking distance from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom ( King, Queen+ Twin), 1-bath beach cottage in the heart of Walnut Beach. Perfect for family vacations, wedding guests, or Yale visitors, our modern farmhouse-style home features a full kitchen, a private backyard with a fire pit, and peaceful coastal vibes. Walk to the sand, celebrate at Tyde, enjoy coffee on the porch, and end the day by the fire. Comfort, style, and location — all in one unforgettable stay!

Kitchen · Family · Beach

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

Family · Kitchen · View

Cozy Studio in Bridgeport

Charming and fully equipped studio located in the heart of Bridgeport. Perfect for business travelers, couples, or solo adventurers, this cozy retreat features a comfortable bed, high-speed Wi-Fi, a private entrance, and a fully stocked kitchen for your convenience. Enjoy easy access to local restaurants, cafes, and shops, as well as public transportation and major highways. Whether you’re here for work or leisure, this studio offers everything you need for a relaxing and stress-free stay.

Kitchen · Indoor spaces · Laundry

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

Family · Kitchen · Layout

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!

Family · Kitchen · Wi-Fi

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

Kitchen · Indoor spaces · Laundry

Beautifully Restored Barn With New England Charm

Set back from the road on one wooded acre with a brook, this renovated 4-bedroom converted barn pairs rustic New England character with modern comfort. Expect 30-foot ceilings, exposed beams, oversized windows, a babbling brook, large yard, eclectic art and furniture, a grand piano, a stocked kitchen, deck, grill, and space to gather. A memorable Fairfield stay for families, couples, small groups, beach weekends, and quiet escapes.

Indoor spaces · Family · Nearby

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.

Indoor spaces · Family · Getting around

Cozy Colonial - Private Hot Tub & Entire House

The way Airbnb was meant to be, something special... a home away from home. No long rule book, just be respectful. Come and stay in this cozy colonial home centrally located in Stratford CT. Walk to the park, soak in the spa, sip tea, listen to music, play games, and relax. Less than 10 minutes from some of the best CT has to offer - beaches, shopping, restaurants, grocery, entertainment, hiking, train to NYC / Yale, and more.

Indoor spaces · Family · Access

Charming Historic Cottage in the Redwoods

Travel back in time to Marchant Farm and enjoy an authentic farm life experience in the historic, newly restored Sunflower Cottage. Whether you need a place to recharge or to reconnect with nature, you will find it here. Relax and unwind in the stunning floor to ceiling cedar living area. With 2 air conditioned bedrooms, each with full beds, and the children's magical loft space with two twin beds and play area.

Indoor spaces · Family · Breakfast

Cozy Cottage with Fire Pit, near Beach

Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities.

Family · Indoor spaces · Access