Middlefield vacation rentals

We found 138 vacation rentals — enter your dates for availability

Discover a selection of 5 homes and other vacation rentals in Middlefield that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include a garden and pool. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.

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Find out more about Middlefield

Why visit Middlefield

  • Outdoor Adventures: Middlefield offers a variety of scenic national and urban parks, perfect for hiking, picnicking, and nature exploration.
  • Rich History: Discover local culture and history at nearby colleges and universities, showcasing the area's educational heritage.
  • Winter Sports: Experience thrilling skiing opportunities, making it a great destination for winter sports enthusiasts.
  • Family-Friendly Activities: Enjoy numerous activities suitable for families, ensuring a fun-filled vacation for all ages.
  • Cozy Accommodations: Choose from a range of vacation rentals, including charming cottages and comfortable apartments, for a perfect home base.

Popular types of accommodation in Middlefield

If you’re planning a getaway to Middlefield, you’ll find a variety of vacation rental options to suit your needs. Our most popular accommodations include houses, cozy cottages, and comfortable apartments. Whether you’re searching for rentals near Middlefield or looking for house rentals with suitable amenities, we’ve got you covered. Enjoy the perfect home base for your adventures in this charming destination.

  • Houses: The top choice for visitors to Middlefield, offering spacious and comfortable accommodations perfect for families or groups.
  • Cottages: A charming option, these cozy retreats provide a delightful atmosphere for a relaxing getaway.
  • Apartments: Ideal for solo travelers or couples, these fully-equipped spaces offer convenience and a home-like feel.
  • Cabins: Perfect for those seeking a rustic escape, cabins immerse you in nature while providing essential comforts.
  • Condos: These modern properties offer a blend of luxury and convenience, making them a popular choice for vacationers.**

Top attractions near Middlefield

Middlefield, Connecticut offers a fantastic blend of outdoor adventures and cultural experiences, making it an ideal destination for vacationers. Explore the scenic national state parks and urban parks, or delve into the rich history at local colleges and universities. Whether you're seeking thrilling skiing opportunities or family-friendly activities, Middlefield has something to cater to every traveler’s taste.

  • Wesleyan University: A historic institution with rich cultural vibes, Wesleyan University features beautiful architecture and a vibrant campus life, just 4 miles from Middlefield. Explore its art galleries and theaters that host a variety of performances.
  • Wadsworth Mansion: Located 2 miles from Middlefield, this elegant event venue exudes business vibes with its stunning architecture and manicured grounds, making it perfect for conferences and special occasions.
  • Choate Rosemary Hall: This modern college preparatory school, situated 7 miles away, offers city vibes with its contemporary facilities and engaging academic environment, promoting a dynamic student experience.

Things to do recommended for couples

For a romantic getaway in Middlefield, explore the thrilling slopes at Powder Ridge Mountain Park, just 2 miles away. Enjoy a fun-filled round at Putter's Paradise Mini Golf, 6 miles away, or savor exquisite wines at Paradise Hills Vineyard, 5 miles away—perfect for an unforgettable couple's experience.

Things to do recommended for families

During your family vacation in Middlefield, Connecticut, enjoy thrilling adventures at Brownstone Exploration & Discovery Park, catch a game at Falcon Field, and explore the cosmos at Van Vleck Observatory. Each destination offers unique experiences that are perfect for creating lasting memories with your loved ones.

Things to do recommended for groups

Experience a night of culture and entertainment at the Toyota Oakdale Theatre, just 8 miles away. Enjoy a round of golf at the Indian Springs Golf Club, right in Middlefield, or explore shopping and dining at Cromwell Commons Shopping Center, located 6 miles from your stay.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, or pets, or planning an extended stay, be sure to use the appropriate filters to match your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Middlefield with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group get-togethers. Thankfully, you can easily filter for these options and many others on Vrbo.
  • Traveling to Middlefield with young kids: Traveling with young kids can be quite an undertaking. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Middlefield: For many families, a vacation isn’t truly fulfilling unless their furry companion is there to share the experience. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Middlefield: If you're in search of vacation rentals that offer 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Middlefield

Middlefield, Connecticut, offers a delightful blend of outdoor adventures and charming neighborhoods perfect for a relaxing getaway. Explore the nearby areas boasting family-friendly vibes and scenic views, or venture to the Cincinnati Riverfront for a taste of local culture. Whether you're seeking a budget-friendly escape or a business trip with a touch of leisure, Middlefield's welcoming atmosphere and friendly people promise an unforgettable experience.

  • Meriden: Located 5 miles from Middlefield, Meriden is a vibrant city that offers a rich blend of family-friendly activities, cultural experiences, and outdoor adventures. Visitors can enjoy various educational venues and theaters, or hit the local golf courses for a relaxing day. Notable attractions include a historic college university and an event conference venue, making it a great spot for both leisure and learning. Don't miss the nearby theme park, perfect for families looking for a fun day out.
  • Middletown: Just 4 miles away from Middlefield, Middletown is known for its cultural charm and outdoor settings, making it an ideal romantic getaway. Explore the local educational institutions and enjoy a round of golf before attending a music concert that showcases both local talent and renowned artists. The city's historic college university and event conference venues add to its appeal, while a nearby beach offers a perfect escape for sunbathing and relaxation.
  • Rockfall: A mere 1 mile from Middlefield, Rockfall is a charming city that presents a mix of culture, family activities, and urban vibes. The area is known for its educational opportunities and shopping areas, making it a great place to spend your day. Explore the historic college university and visit the tourist precinct, where you can discover local shops and eateries. Don't forget to check out the town hall, a key landmark that adds to the city’s unique character.

Best time to go to Middlefield

If you're planning a trip to Middlefield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like March to April and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January29.1°F (-1.6°C)Light RainMostly SunnyAverageSlightly Low
February30.6°F (-0.8°C)Light RainMostly CloudyAverageSlightly Low
March37.6°F (3.1°C)Light RainMostly SunnySlightly LowSlightly Low
April48.4°F (9.1°C)Light RainMostly SunnySlightly LowAverage
May58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
June66.9°F (19.4°C)Light RainMostly SunnyAverageSlightly High
July73.8°F (23.2°C)Light RainMostly SunnySlightly HighSlightly High
August72.1°F (22.3°C)Light RainMostly SunnySlightly HighSlightly High
September65.3°F (18.5°C)Light RainMostly SunnySlightly HighAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
November43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage
December35.4°F (1.9°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, use our filters to narrow down your search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient area for you to plan new adventures, refine your travel arrangements, or manage your existing reservations. Your saved and booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To start exploring your Trip Boards, head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the majestic landscape of Middlefield

The waterfalls and mountains create a pretty picture of Middlefield. Renowned for its hiking, biking and golfing, this city welcomes all visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Middlefield

Are you hoping to find things to do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Middlefield a one-of-a-kind vacation spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Powder Ridge Mountain Park and Resort (1.8 mi / 3 km)
  • Brownstone Exploration & Discovery Park (5.3 mi / 8.5 km)
  • TPC River Highlands (8.8 mi / 14.1 km)
  • Hawks Landing Country Club (11.3 mi / 18.2 km)
  • Mount Southington Ski Area (11.9 mi / 19.1 km)
  • Chatfield Hollow State Park (12.1 mi / 19.5 km)

Exploring the natural landscape of Middlefield

Whether you're an outdoor enthusiast or just want to take in the scenery, Middlefield is a great spot to appreciate mother nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Lake Beseck Beach (1.2 mi / 1.9 km)
  • Falcon Field (3.8 mi / 6.1 km)
  • Silver Lake State Access Area (5.5 mi / 8.9 km)
  • Connecticut River State Wildlife Area (5.8 mi / 9.3 km)
  • Dinosaur State Park (9.6 mi / 15.5 km)
  • Mount Carmel (11.9 mi / 19.2 km)

Transportation to and around Middlefield

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 19.5 mi (31.3 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Oxford, CT (OXC-Waterbury - Oxford), which is 22.2 mi (35.8 km) away.

Frequently asked questions

How much does it cost to rent a vacation home in Middlefield?
Prices for vacation rentals in Middlefield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Middlefield to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Middlefield vacation house rentals?
You can find great discounts on house rentals in Middlefield on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Middlefield?
For renting a beach house in Middlefield, travelers should consider nearby areas along the Connecticut shoreline, particularly in towns like Madison and Guilford. Madison offers beautiful beach access at locations such as Hammonasset Beach State Park, where vacation rentals often feature spacious decks, outdoor grills, and easy access to the sandy shores. Many properties in this area are family-friendly and equipped with amenities like beach gear, picnic areas, and large dining spaces for gatherings.

Guilford, known for its picturesque town green and historic district, also presents great options for beach house rentals. Here, visitors can find charming cottages that typically include modern kitchens, cozy living rooms, and private outdoor spaces for relaxation. Proximity to local shops, restaurants, and the scenic Guilford Harbor enhances the appeal of this area.

Additionally, the shoreline towns provide various recreational activities, such as kayaking and paddleboarding, making it easy for guests to enjoy the coastal experience.
Where are the best Middlefield ski resort rentals?
For skiing near Middlefield, travelers should consider rentals in the nearby town of Meriden, which is conveniently located for accessing local ski areas. The closest ski resort is Mount Southington, just a short drive away. In Meriden, you can find a variety of vacation rentals, including cozy cabins and modern townhomes that are well-suited for families and groups. Many of these properties come with amenities such as fully equipped kitchens, spacious living areas, and some even feature fireplaces for a warm and inviting atmosphere after a day on the slopes.

Additionally, the area around Mount Southington offers several lodges and inns that provide convenient access to skiing. These accommodations often include amenities like ski storage, complimentary breakfast, and easy shuttle service to the slopes, making it convenient for those looking to maximize their time on the mountain.

For those looking to explore the surrounding region, there are also opportunities for winter hiking and snowshoeing in nearby parks, with rentals typically featuring easy access to these outdoor activities.
What is the most popular type of vacation rental accomodation in Middlefield?
In Middlefield, vacation houses are the most popular type of rental, with several available throughout the area. These houses typically offer spacious rooms with multiple bedrooms, fully equipped kitchens, and outdoor spaces for enjoying the serene surroundings. Cottages are also a favored option, providing a charming and rustic feel, often featuring cozy interiors and gardens for relaxation. Additionally, there are several apartments that cater to those seeking a more compact living space, generally including essential amenities like kitchen facilities and comfortable living areas.
Are there any family house rentals in Middlefield?
In Middlefield, Connecticut, there are some available family-friendly house rentals, with around 13 options to choose from. This charming town offers a peaceful environment, superb for families looking to enjoy nature and outdoor activities. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to play safely.

Visitors can explore nearby attractions such as the picturesque Lake Beseck, where fishing and hiking opportunities abound, or the scenic trails of the nearby Machimoodus State Park, which is great for family outings.
Can I find long-stay vacation rentals in Middlefield?
A long-stay vacation rental in Middlefield is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Middlefield?
In Middlefield, Connecticut, there are several remote work vacation rentals available—specifically, around 13 options that cater to those seeking a productive environment. These rentals often come equipped with essential amenities for remote work, including high-speed internet, dedicated workspaces with desk chairs, and comfortable living areas that allow for a seamless work-life balance.

Travelers can expect properties that provide free Wi-Fi, enabling efficient connectivity for virtual meetings or project work. The charming town offers a peaceful atmosphere, ideal for concentration, while still being close enough to local attractions and outdoor spaces for relaxation after a busy workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middlefield vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Middlefield with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Middlefield?
In Middlefield, popular vacation rental amenities include well-equipped kitchens, allowing travelers to prepare their own meals conveniently. Many properties also feature outdoor spaces like decks or patios, where guests can relax and enjoy the natural surroundings. Air conditioning is commonly available, ensuring comfort during warmer months, while onsite parking makes it easy for visitors to arrive with their vehicles.
When is the best time to visit Middlefield for a vacation rental?
The best time to visit Middlefield for a vacation rental is during the peak season from July to September. This period is particularly vibrant, as families and outdoor enthusiasts flock to the area to enjoy the warm summer weather and partake in various activities. With temperatures typically ranging from the mid-70s to low 80s Fahrenheit, it's an ideal time for hiking, biking, and exploring the beautiful landscapes of Connecticut.

July stands out as the most popular month, filled with numerous local events and festivals that highlight the charm of Middlefield. Visitors can experience firsthand community gatherings, farmers' markets, and outdoor concerts, all while enjoying the picturesque surroundings.

For those looking for a more budget-friendly option, consider visiting in March. This month offers a quieter atmosphere, allowing you to appreciate the early signs of spring and explore the scenic parks and trails without the summer crowds. The mild weather, typically in the 40s to low 50s Fahrenheit, can still be quite pleasant for leisurely strolls or enjoying the local dining scene.

Ultimately, the best time to book a vacation rental in Middlefield depends on your preference for lively summer activities or a more tranquil experience during the shoulder months.
How early should I book a Middlefield vacation rental?
Book your Middlefield vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Middlefield, Connecticut, United States of America?
In Middlefield, Connecticut, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. One of the main points of interest is the Wadsworth Falls State Park, which features picturesque waterfalls, hiking trails, and picnic areas, making it a great spot for outdoor activities. The park is particularly popular for its scenic views and the chance to explore the surrounding forests.

Another highlight is the Lyman Orchards, a historic farm offering seasonal fruit picking, a market with local produce, and beautiful walking trails. This family-friendly destination is superb for those looking to enjoy the agricultural heritage of the area.

Middlefield is also close to the historic town of Durham, where visitors can explore quaint shops and charming eateries. The nearby Quinnipiac River offers opportunities for fishing and kayaking, enhancing the outdoor experience for nature enthusiasts.
Can I change or cancel my Middlefield home rental booking on Vrbo?
To find Middlefield vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Middlefield vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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