Middletown, Connecticut Vacation Rentals

Discover a variety of rental homes and villas in Middletown, Connecticut for your upcoming trip, whether it's for leisure or work. Indulge in a more customized stay with private vacation home rentals that offer an array of amenities and home features. With a wide selection of available homes, you can find a vacation home that suits your preferences and budget. However you're looking to experience your stay, Homes and Villas by Marriott has your next vacation home waiting.

Types of vacation rentals in Middletown

Where to stay in Middletown

Show all homes

Booking a vacation rental in Middletown, Connecticut?

Here are some things to know to support your visit:

Middletown Overview
Nestled in the heart of New England, Middletown, Connecticut, is a hidden gem that offers an enchanting blend of historic charm, cultural richness, and serene natural landscapes. This picturesque city, perched on the banks of the Connecticut River, is an idyllic retreat for those seeking a tranquil getaway with the comforts of a private home. Imagine waking up in a cozy, private residence, a space that's entirely your own, where you can sip your morning coffee in a sun-drenched garden or by a private swimming pool—a common amenity in many of Middletown's rental homes. The city's residential areas boast a selection of pet-friendly accommodations, ensuring that your furry friends can join in on the adventure. Middletown's allure is magnified by its famous attractions, such as the prestigious Wesleyan University. The university's campus is not just for students; it's a cultural hub where visitors can admire the architecture, stroll through the grounds, and enjoy performances at the Center for the Arts. The city's commitment to culture is palpable, with a vibrant downtown that features historic buildings, unique boutiques, and a culinary scene that caters to every taste—from quaint cafes to gourmet farm-to-table restaurants. For history buffs, the Middlesex County Historical Society offers a window into Middletown's storied past, from its indigenous heritage to its pivotal role in American history. Meanwhile, nature lovers will find solace in the city's green spaces, such as the enchanting Wadsworth Falls State Park, where a hike leads to a breathtaking waterfall, or Harbor Park, which offers panoramic views of the Connecticut River and serves as an ideal setting for picnics and strolls. The city's Main Street is the heartbeat of Middletown, alive with festivals that celebrate the arts and the community's diverse cultures. It's also home to the Kidcity Children's Museum, a wonderland for young explorers. And for those with a taste for fine wine, Middletown is a gateway to the Connecticut Wine Trail, inviting oenophiles to discover the region's exquisite vineyards. Middletown's proximity to the water also means that visitors can enjoy the quintessential New England experience of a day at the beach or on the waterfront, with activities ranging from boating to simply relaxing by the river's edge. In Middletown, Connecticut, every moment is an opportunity to create lasting memories, whether you're basking in the privacy of your rented home, delving into the local culture, or embracing the natural beauty that surrounds you. It's a place where the simple pleasure of a New England lifestyle is yours to discover.
Cultural Attractions in Middletown
Middletown, Connecticut, nestled in the heart of the state, offers a charming blend of New England history, vibrant arts, and rich cultural experiences that are sure to delight any traveler with a passion for cultural activities. Begin your exploration at Wesleyan University's Center for the Arts, a hub for creative expression that features an array of performances, exhibitions, and events throughout the year. The university's campus is also home to the Davison Art Center, which houses an impressive collection of prints and photographs, and the Wesleyan Potters, a cooperative guild for ceramic arts. For a deep dive into local history, the Middlesex County Historical Society provides a window into Middletown's past. Housed in the General Mansfield House, the society's museum showcases artifacts and exhibits that tell the story of the city and its people, from the Indigenous inhabitants to the present day. Art enthusiasts will find a treasure trove at the Middletown Art Center, where local artists display their work and the community comes together for art classes and workshops. The Main Street Market is another cultural gem, where you can explore a variety of shops and galleries that reflect the creativity of the region. Live music thrives in Middletown, with venues like The Buttonwood Tree Performing Arts & Cultural Center offering an intimate setting for a wide range of musical performances, including jazz, folk, and world music. The center also hosts poetry readings, open mics, and other community events that celebrate the arts. Middletown's culinary scene is a reflection of its cultural diversity, with restaurants serving up everything from traditional New England fare to international cuisine. Be sure to visit the local farmers' market to sample fresh, locally-sourced produce and artisanal goods. Throughout the year, Middletown hosts a variety of festivals and events that showcase local customs and community spirit. The Middletown Pride event celebrates diversity and inclusion, while the Middletown Music Festival brings together musicians and music lovers from across the region. In Middletown, the blend of collegiate energy, historical charm, and artistic vibrancy creates a cultural landscape that is both enriching and welcoming. It's a place where the arts are not just observed but lived, making it an ideal destination for those who seek to immerse themselves in cultural experiences.
Kids IconFamily friendly activities in Middletown
Middletown, Connecticut, is a charming New England city that offers a variety of activities for families traveling with children. Nestled along the Connecticut River, Middletown provides a blend of cultural experiences, outdoor adventures, and educational opportunities that will keep kids engaged and entertained. One of the city's highlights for families is Kidcity Children's Museum. This hands-on museum is designed for children up to age 7 and features imaginative play areas that encourage creativity and learning. Kids can explore a medieval village, pilot a fishing boat, or become a short-order cook in a pretend diner. The museum's interactive exhibits are perfect for an afternoon of fun and discovery. For outdoor enthusiasts, the Wadsworth Falls State Park is a must-visit. With its easy hiking trails, picturesque waterfalls, and picnic areas, it's an ideal spot for a family day out. Children can enjoy the natural beauty of the park, splash in the water during the warmer months, and parents can relax amidst the serene environment. The Middletown Nature Gardens is another great outdoor destination. It offers a peaceful setting where kids can learn about local flora and fauna. The gardens are a wonderful place for a leisurely walk, and the educational signage helps children understand the importance of conservation and the ecosystem. Families can also take a stroll along the scenic Harbor Park, where they can watch boats on the river and enjoy the playground. The park is a great location for a picnic with its ample green space and beautiful views. For a taste of local culture, the Oddfellows Playhouse Youth Theater provides theatrical performances that are both entertaining and suitable for children. The playhouse offers a range of shows throughout the year, giving families the chance to enjoy live theater together. When it comes to dining, Middletown has several family-friendly restaurants that cater to young palates. From classic American fare to international cuisine, there's something to satisfy everyone in the family. In Middletown, Connecticut, families will find a welcoming community with plenty of activities to keep children happy and engaged. Whether it's exploring a museum, hiking through nature, or enjoying a live performance, Middletown offers a delightful experience for visitors of all ages.
Nature IconOutdoor activities in Middletown
Middletown, Connecticut, nestled in the heart of the state, offers a serene escape into nature for those who seek the tranquility of the outdoors. The city is surrounded by a variety of natural landscapes, from rolling hills to peaceful rivers, providing a plethora of activities for nature enthusiasts. Wadsworth Falls State Park is a local favorite, featuring two sets of falls—the Big Falls and the Little Falls—surrounded by a lush forest. The park offers over 250 acres of hiking trails, picnic areas, and a designated swimming area, making it a perfect spot for a day of exploration and relaxation. The trails are suitable for all levels of hikers and provide a picturesque backdrop for a leisurely walk or a more challenging trek. For those who enjoy water-based activities, the Connecticut River presents a splendid opportunity for kayaking, canoeing, and fishing. The river's calm waters are ideal for paddlers of all skill levels, and the scenic views along the banks are a delight for photographers and nature lovers alike. Another gem is the Guida Farm Conservation Area, which offers a tranquil setting for bird watching, walking, and enjoying the beauty of meadows and woodlands. The conservation area is home to a variety of wildlife and is a great place to observe the changing seasons in New England. For a unique outdoor experience, visit the Middlesex County Blue Trail System. This extensive network of trails leads adventurers through diverse habitats, including forests, fields, and wetlands. The Blue Trails are well-maintained and marked, providing a safe and enjoyable hiking experience for visitors. If you're looking for a more leisurely outdoor activity, Harbor Park is the place to be. Located along the Connecticut River, the park features a boardwalk, perfect for a sunset stroll, and ample green space for picnicking with a view of the water. Lastly, for those who appreciate a good round of golf amidst natural beauty, the Lyman Orchards Golf Club offers two 18-hole championship courses. The courses are set on a picturesque landscape with sweeping views of the surrounding countryside, providing a challenging yet enjoyable experience for golfers. Middletown, Connecticut, with its diverse natural attractions and outdoor activities, is a haven for those who wish to connect with nature and enjoy the great outdoors. Whether you're seeking adventure or a peaceful retreat, Middletown's natural wonders are sure to provide an unforgettable experience.
Weather IconWeather in Middletown
Middletown, Connecticut, experiences a humid continental climate, which brings distinct seasons with a range of temperatures and weather conditions. The city's weather is influenced by its location in the northeastern United States, with the Atlantic Ocean to the east and the Appalachian Mountains to the west. The summer months, from June to August, are warm and often humid, with average high temperatures in the low to mid-80s Fahrenheit (around 27-30°C). This is also when humidity levels are at their highest, which can make the heat feel more oppressive. Summer is also the time for occasional thunderstorms, contributing to the city's annual precipitation. The winter months, from December to February, are cold with average high temperatures in the mid-30s Fahrenheit (around 1-3°C) and lows often dropping below freezing. Snowfall is common, with the city receiving an average of 30-40 inches of snow annually. Winter weather can be quite variable, with occasional mild spells followed by cold snaps. Spring, from March to May, is a season of transition, with temperatures gradually warming from the 40s to the 60s Fahrenheit (around 4-15°C). This season can be unpredictable, with late snowfalls in March or early April, followed by rapidly warming temperatures and the onset of spring rains. Fall, from September to November, is many residents' and visitors' favorite time of year. Temperatures cool from the 70s to the 50s Fahrenheit (around 21-10°C), and the humidity drops, making for crisp and comfortable weather. This is also when Middletown's foliage turns into a spectacular display of oranges, reds, and yellows, creating a picturesque New England autumn. The most popular time to visit Middletown is during the fall, when the weather is at its most pleasant and the fall foliage is at its peak. However, each season offers its own unique appeal, from the vibrant greenery and blossoming flowers of spring to the snow-covered landscapes of winter, which can be particularly enchanting during the holiday season. For those looking for the most comfortable weather conditions, late spring and early fall typically provide mild temperatures and lower humidity, ideal for exploring the city's historic downtown, scenic riverfront, and surrounding natural beauty.
Transportation in Middletown
Middletown, Connecticut, a charming New England city nestled along the Connecticut River, offers a variety of transportation options for visitors. While it may not have the extensive transit systems of a major metropolis, getting to, from, and around Middletown is still quite manageable. Travelers typically arrive in Middletown by car, as it is conveniently located off of Route 9, which connects to the larger Interstate 91 and Interstate 95. This makes Middletown easily accessible from major cities like New York and Boston. For those without a car, bus services such as Middletown Area Transit (MAT) provide connections to nearby cities and towns, including a link to the larger CT Transit system that services much of Connecticut. The closest major airport is Bradley International Airport, located approximately 30 miles north of Middletown near Hartford. From there, visitors can rent a car or take a shuttle service to reach Middletown. Additionally, the city is accessible by train, with the nearest Amtrak stations located in Meriden and Berlin, both of which are about a 20-minute drive away. Within Middletown itself, MAT operates several bus routes that cover the city and its immediate surroundings. These buses provide a convenient way to reach key areas, including shopping centers, the downtown district, and Wesleyan University's campus. For those who prefer a more personalized mode of transport, taxis and ride-sharing services like Uber and Lyft are available. Middletown is moderately walkable, especially in the downtown area where there is a concentration of restaurants, shops, and cultural attractions like the historic Main Street. The city's layout makes it pleasant for strolling, and visitors can enjoy the mix of historic architecture and the scenic beauty of the riverfront. However, to fully explore the wider area, including attractions that are farther afield or to take advantage of the natural landscapes surrounding the city, having access to a car is recommended. In conclusion, Middletown's transportation options cater to a variety of preferences, whether you're arriving by car, bus, or train. While the city itself can be enjoyed on foot, particularly in the downtown area, having access to a car or using the local bus service will enhance your ability to explore all that Middletown and the surrounding region have to offer.