Middlesex County vacation rentals

We found 730 vacation rentals — enter your dates for availability

Select from 212 homes, 88 cottages, and other vacation rentals in Middlesex County to find one that's perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the best amenities for spending time at your vacation home, which might include WiFi and a washer and dryer. No matter what you're looking for, you'll be able to choose a rental to meet everyone's needs, including accessible or non-smoking choices.

Popular cities in Middlesex County

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Find out more about Middlesex County

Find out more about Middlesex County

Why visit Middlesex County

  1. Outdoor Adventures: Enjoy stunning state parks and beautiful beaches perfect for hiking, picnicking, and water activities.
  2. Cultural Experiences: Visit historic colleges and universities that enrich the local culture and heritage.
  3. Charming Neighbourhoods: Explore vibrant communities filled with friendly locals and unique shops.
  4. Romantic Getaways: Experience idyllic settings ideal for couples seeking a romantic escape.
  5. Diverse Accommodations: Choose from cozy cottages to modern apartments tailored to every traveller's needs.

Popular types of accommodation in Middlesex County

Planning a getaway to Middlesex County? Discover the charm of this beautiful region by exploring a variety of vacation rentals. From cozy cottages and houses to modern apartments, there’s something for every traveller. Whether you’re interested in monthly rentals or a weekend escape, Middlesex County offers a range of options to suit your needs. Dive into your perfect stay and experience all that this delightful area has to offer!

  • Houses: The top choice for visitors in Middlesex County, offering spacious and comfortable living for families or groups.
  • Cottages: A delightful option for a quaint and peaceful escape, perfect for those seeking charm and tranquillity.
  • Apartments: Ideal for solo travellers or couples, these units provide a convenient and modern stay in the heart of the area.
  • Cabins: A favourite among nature enthusiasts, these rustic hideaways offer a unique experience amidst the great outdoors.**

Top attractions in Middlesex County

Middlesex County, Connecticut, offers a delightful escape for outdoor lovers and those seeking a romantic getaway. With a variety of attractions including stunning state parks, beautiful beaches, and historic colleges and universities, visitors can enjoy a mix of adventure and cultural experiences. Whether you're travelling solo, with family, or as a couple, this charming region promises memorable adventures and picturesque scenery to explore.

  1. Wesleyan University: A historic liberal arts university that boasts stunning architecture and a vibrant campus culture. Visitors can explore its art galleries, attend performances, and enjoy the beautiful grounds.
  2. Essex Steam Train: A charming railway museum where you can experience the nostalgia of vintage steam train rides through picturesque landscapes. It's a delightful way to learn about the region's history and transportation.
  3. Harvey's Beach: A serene beach perfect for relaxation and family fun. Enjoy sunbathing, swimming, or picnicking while soaking in the peaceful coastal atmosphere.

Things to do recommended for couples

For a romantic getaway in Middlesex County, explore Powder Ridge Mountain Park for outdoor adventures together. Savor the enchanting atmosphere at Chamard Vineyards and Arrigoni Winery, where you can indulge in wine tastings amidst beautiful landscapes. Perfect spots for creating cherished memories as a couple!

Things to do recommended for families

Experience the thrill at Brownstone Exploration & Discovery Park and Stay and Play LLC, both offering adventurous arcade zones perfect for families. Don't miss the Van Vleck Observatory for a fun and educational look at the stars, making your Middlesex County vacation memorable!

Things to do recommended for groups

Enjoy a round of golf at TPC River Highlands, indulge in retail therapy at Clinton Crossing Premium Outlets, or experience the charm of the Goodspeed Opera House for a cultural evening. These activities promise a memorable group getaway in beautiful Middlesex County.

What do I need to keep in mind when booking a vacation in Middlesex County

If you're planning a trip with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Middlesex County with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Middlesex County with young kids: Travelling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your location in relation to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Middlesex County: For many, a family vacation wouldn’t feel complete without their furry companion by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Middlesex County: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include criteria like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Middlesex County

Middlesex County, Connecticut, offers a delightful blend of outdoor adventure and charming scenery, making it perfect for a romantic getaway or a family-friendly vacation. Explore vibrant neighbourhoods, relax in pleasant parks, and enjoy the welcoming atmosphere of friendly locals. With nearby gated communities and a variety of scenic spots, you’ll find plenty of opportunities to unwind and connect with nature while soaking in the unique charm of this picturesque region.

  • Old Saybrook: Nestled at the mouth of the Connecticut River, Old Saybrook is a picturesque city that beckons visitors with its stunning outdoor scenery and romantic atmosphere. Known for its charming beaches and family-friendly lakes, this coastal gem offers a myriad of activities, including golfing and exploring nearby recreational areas. Don't miss the opportunity to visit local casinos for an exciting night out, or simply relax on the sandy shores and soak in the breathtaking views of the Long Island Sound.
  • Westbrook: Westbrook is a coastal city that embodies the essence of New England charm, attracting those seeking outdoor adventures and romantic getaways. With its pristine beaches and family-friendly resorts, it’s an ideal spot for relaxation and recreation. Visitors can enjoy musical concerts at local venues or try their luck at nearby casinos. The vibrant community hosts various events throughout the year, making it a lively destination for tourists and locals alike. The scenic coastal views further enhance the travel experience.
  • Middletown: Located in the heart of Middlesex County, Middletown is a city rich in culture and history. It offers a unique blend of outdoor activities and educational experiences, with historic universities and colleges dotting the landscape. Visitors can explore the scenic riverfront parks or engage in recreational activities such as golfing. The city also features various event venues for conferences and gatherings. With its vibrant arts scene and numerous beach spots, Middletown is a delightful destination for those seeking romance and culture.

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, make use of our filters to search by price, location, and type of vacation rental. We’re here to help you find the perfect place for your getaway!

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform for you to plan new journeys, manage your existing itineraries, or review and organise your reservations. The properties you’ve either saved or booked are neatly categorised into Potential, Upcoming, or Current Trips. To check out the Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Middlesex County getaway

Learn about the unique charm of Middlesex County with a stay in a private vacation home. This city has something for everyone. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Middlesex County

Are you hoping to find attractions to see during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Middlesex County a fun place to get away. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Machimoodus State Park (3.9 mi / 6.3 km)
  • Chatfield Hollow State Park (7 mi / 11.2 km)
  • Brownstone Exploration & Discovery Park (10 mi / 16.1 km)
  • Chamard Vineyards (10.8 mi / 17.4 km)
  • Powder Ridge Mountain Park and Resort (11.2 mi / 18 km)
  • TPC River Highlands (13.3 mi / 21.4 km)

Exploring the natural features in Middlesex County

Whether you're looking for fun outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Middlesex County. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Chatfield Hollow State Park (7 mi / 11.2 km)
  • Wadsworth Falls State Park (9.4 mi / 15.2 km)
  • Connecticut River State Wildlife Area (10.6 mi / 17.1 km)
  • Lake Beseck Beach (11.2 mi / 18.1 km)
  • Lake Hayward (11.4 mi / 18.3 km)
  • Goose Island (12.6 mi / 20.3 km)

Transportation options to and around Middlesex County

If you're traveling by train, make your way to Clinton Station or Old Saybrook Station and explore the city from there.

Frequently asked questions

What is the best area to stay in Middlesex County when booking a vacation rental?
Old Saybrook is among the more popular locations to select a vacation property in Middlesex County. Searching for some fun things to do in this destination? Don't miss Essex Steam Train and Hammonasset Beach State Park.
What is the most popular type of vacation rental accommodation in Middlesex County?
The most popular types of vacation rentals in Middlesex County are houses. Prefer something different? Vrbo has many options to match our guests' needs, so you'll see vacation properties in all shapes and sizes, and for all budgets. The ideal fit is ready and waiting for you — snap up yours today.
How much does it cost to rent a vacation rental in Middlesex County?
The average price for a vacation home in Middlesex County depends on a number of factors, including time of year, length of stay and property type. Whether you're dreaming about a sprawling villa with lots of space or a quaint cabin perfect for just you and the kids, just add your dates of travel to discover stays with great value.
How much does it cost to rent a beach house in Middlesex County?
The average price for a vacation home by the beach in Middlesex County will depend on when you'll be there and the type and size of property you're looking for. You can find prices quickly and easily on Vrbo by entering your travel dates and destination. Then make use of the filter tool to choose the number of bedrooms and amenities that you prefer, such as air conditioning, a pool and WiFi.
What are popular rental amenities in Middlesex County?
When it comes to rental amenities that guests are searching for in Middlesex County, a stovetop, a fridge and a microwave oven rank highest. With Vrbo vacation rentals, you'll enjoy choices to match your style and taste, whether you're vacationing with friends, family or even pets.
Are there large group vacation rentals in Middlesex County?
Middlesex County has 29 vacation rentals that can fit 10 or more people. These properties come with the space and privacy you need to share good times with family and friends.
What are the top attractions for families in Middlesex County?
Keep the kids amused at these top family-friendly attractions in Middlesex County:

  • Clinton Crossing Premium Outlets
  • TPC River Highlands
  • Essex Steam Train

Can I find two-bedroom vacation rentals in Middlesex County?
Gather your loved ones and enjoy peace, privacy and comfort in one of the 39 two-bedroom vacation properties Middlesex County has to offer.
Are there vacation rentals with WiFi in Middlesex County?
Whether you want to keep up with world events, send some emails or post a pic to social media, there are 104 vacation homes with WiFi in Middlesex County. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How old do you have to be to rent a vacation rental in Middlesex County?
The minimum age can differ across properties on Vrbo, so double-check the rules of the vacation home in Middlesex County you want. But in general, it's 16, 18 or 21.
How long can I rent a vacation rental in Middlesex County for?
The amount of time you can stay in a Middlesex County vacation rental for depends on each property. Simply tap in your travel dates to view options that offer long-term stays. They include all the things you need to make your extended break more convenient and comfortable, like air conditioning and laundries. Some Vrbo vacation properties may also offer discounted weekly or monthly prices, so you can stay even longer for less.

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