Cheshire vacation rentals

We found 264 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Cheshire to find one that's perfect for your trip. Vacation rentals offer the best amenities for your family, friends, or furry companion, such as a fireplace and a washer and dryer. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

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Find out more about Cheshire

Why visit Cheshire

  • Family-Friendly Activities: Enjoy a variety of attractions perfect for families, including parks and recreational areas.
  • Cultural Experiences: Discover historic colleges and universities that add to the rich local culture.
  • Outdoor Adventures: Explore national and state parks for hiking, biking, and scenic views.
  • Charming Neighborhoods: Stroll through picturesque neighborhoods filled with unique shops and dining options.
  • Diverse Accommodations: Choose from charming cottages, spacious homes, and cozy apartments for a comfortable stay.

Popular types of accommodation in Cheshire

Planning a getaway to Cheshire? You're in for a treat. Discover a diverse array of vacation rentals, including charming cottages, spacious private homes, and cozy apartments. Whether you’re seeking a pet-friendly option or a relaxing vacation home, Cheshire has something for everyone. Explore our selection of vacation home rentals and find the perfect place to unwind and make lasting memories.

  • Houses: The top choice for visitors to Cheshire, these homes offer spacious and comfortable living for families or groups, ensuring a home-like experience during your stay.
  • Cottages: A delightful option for a quaint and cozy getaway, ideal for couples or small families seeking charm and tranquility.
  • Apartments: Perfect for solo travelers or couples, apartments provide convenient amenities in a more urban setting.
  • Condos: These modern accommodations blend comfort and style, often featuring shared amenities like pools and fitness centers.
  • Villas: Offering luxury and privacy, villas are an excellent choice for those looking for an upscale retreat in Cheshire.**

Top attractions near Cheshire

Cheshire, Connecticut, is perfect for family-friendly, cultural, and outdoor vacations. Visitors can enjoy a variety of attractions, including urban parks, historic colleges and universities, and national and state parks. Whether you're seeking outdoor adventures, family-oriented activities, or cultural experiences, Cheshire offers a diverse range of options to explore and enjoy during your visit.

  • Quinnipiac University: A historic institution with beautiful architecture and a vibrant campus culture, it offers visitors a glimpse into academic life and engaging events.
  • Choate Rosemary Hall: This modern college preparatory school features impressive facilities and a dynamic atmosphere, showcasing a blend of tradition and innovation in education.
  • Lake Compounce: An exciting amusement park perfect for families, it boasts thrilling rides and outdoor activities, ensuring a fun-filled day for all ages.

Things to do recommended for couples

Cheshire offers a wonderful getaway for couples. Enjoy skiing at Powder Ridge Mountain Park, savor wine at Paradise Hills Vineyard, or have fun at Putter's Paradise Mini Golf for a mix of adventure and romance. Each experience is just a short drive away for a perfect day together.

Things to do recommended for families

Your family will have a fantastic time at Hubbard Park, just 5 miles from Cheshire, where you can unwind in nature. Falcon Field, 8 miles away, offers thrilling sports activities, while Crystal Bees, 9 miles from Cheshire, promises endless fun in their arcade adventure zone.

Things to do recommended for groups

In Cheshire, groups can enjoy a show at the Toyota Oakdale Theatre for a mix of culture and entertainment. For outdoor enthusiasts, the Cheshire Golf Course offers a great day of sports. Don't miss the Brass Mill Center for shopping and family-friendly fun just 7 miles away.

*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 Cheshire

When you're traveling with a group, family, pets, or planning for extended stays, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Cheshire with a group: Think about how many bedrooms you’ll require, as well as any features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Cheshire with young kids: Traveling with young kids can be quite a task. It’s important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Cheshire: For many families, a trip isn't truly a family affair without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cheshire: If you're searching for 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 rentals. 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 Cheshire

Cheshire, Connecticut, offers a delightful vacation experience for families and culture enthusiasts alike. Surrounded by beautiful scenery, you can explore charming neighborhoods, enjoy a romantic evening, or indulge in outdoor activities. Don’t miss the chance to stroll along scenic routes, especially during the summer season. Nearby cities provide a warm, friendly atmosphere, perfect for budget-conscious travelers looking to create lasting memories. Discover the unique charm of Cheshire and its inviting surroundings.

  • Meriden: Located a mere 6 miles from Cheshire, Meriden is a vibrant city that offers a delightful blend of family-friendly activities and cultural experiences. Visitors can enjoy outdoor adventures at local parks and golf courses or immerse themselves in the arts at various theaters. Meriden is home to notable landmarks like historic universities and event venues, making it a perfect stop for those interested in education and community events. Don't miss the chance to visit the nearby theme park for a fun-filled day with the family.
  • Waterbury: Just 7 miles away from Cheshire, Waterbury is an exciting destination for families and adventure seekers alike. This city boasts a range of outdoor activities and is home to an amusement park and a resort, ideal for a thrilling getaway. Waterbury's local attractions, including a popular waterpark and event venues, provide endless entertainment options for visitors of all ages. Whether you're looking for a fun family day or an adventure-packed experience, Waterbury has something for everyone.
  • Wallingford: Located 6 miles from Cheshire, Wallingford is known for its charming blend of culture, romance, and family experiences. This city offers a variety of activities, including visits to theaters and golf courses, making it a great spot for leisure and entertainment. Wallingford is also close to notable landmarks such as historic and modern universities, which enrich the local atmosphere. With its inviting ambiance, Wallingford is perfect for couples seeking a romantic outing or families looking to create lasting memories.

Best time to go to Cheshire

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January29.1°F (-1.6°C)Light RainMostly SunnyAverageSlightly Low
February30.7°F (-0.7°C)Light RainMostly CloudyAverageSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnyAverageSlightly Low
April48.7°F (9.3°C)Light RainMostly SunnySlightly HighAverage
May59.2°F (15.1°C)Light RainMostly SunnyAverageAverage
June67.5°F (19.7°C)Light RainMostly SunnySlightly HighSlightly High
July74.3°F (23.5°C)Light RainMostly SunnySlightly HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyAverageSlightly High
September65.8°F (18.8°C)Light RainMostly SunnyAverageAverage
October55.0°F (12.8°C)Light RainMostly SunnySlightly LowAverage
November43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage
December35.4°F (1.9°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? Being flexible with your travel dates can help, as prices often vary. Additionally, booking a longer stay typically results in significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your travel needs.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the total booking amount. Being the organizer truly has its perks. Become a member of our One Key rewards program to unlock exclusive savings and accumulate OneKeyCash on qualifying stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new trips, pick up right where you left off, and easily view and organize your travel plans. You can now find the properties you've saved or booked categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the lush landscape of Cheshire

Enjoy the history and other features of Cheshire. Well known for its hiking, waterfalls and shopping, this romantic city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Cheshire

Are you hoping to discover attractions to see in the area? Venture out of your cozy vacation rental and experience everything that makes Cheshire a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Mount Southington Ski Area (5.1 mi / 8.3 km)
  • Powder Ridge Mountain Park and Resort (8.8 mi / 14.2 km)
  • Lake Compounce (9 mi / 14.5 km)
  • Quassy Amusement Park (12.5 mi / 20.1 km)
  • Brownstone Exploration & Discovery Park (14.5 mi / 23.3 km)
  • TPC River Highlands (16.4 mi / 26.4 km)

Exploring the natural features in Cheshire

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Cheshire. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Mount Carmel (5.8 mi / 9.4 km)
  • YMCA Mountain Mist Day Outdoor Center (8.3 mi / 13.4 km)
  • Lake Beseck Beach (9.1 mi / 14.7 km)
  • Beacon Falls Town Recreation Field (9.6 mi / 15.5 km)
  • Wadsworth Falls State Park (11.7 mi / 18.9 km)
  • East Rock Park (12.6 mi / 20.3 km)

Transportation to and around Cheshire

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 12 mi (19.3 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to New Haven, CT (HVN-Tweed - New Haven Regional), which is 16.5 mi (26.6 km) away.

Frequently asked questions

What is the best area to stay in Cheshire, Connecticut, United States of America when booking a vacation rental?
When looking for the best area to stay in Cheshire, Connecticut, you might consider neighborhoods like the center of town, which offers a charming atmosphere and proximity to various amenities. This area is known for its welcoming community vibe, making it an ideal spot for visitors seeking both relaxation and convenience.

One of the top attractions in Cheshire is the historic Cheshire Park, a beautiful green space great for outdoor activities such as walking, picnicking, and enjoying nature. Additionally, the town is home to the renowned Sleeping Giant State Park, which features scenic hiking trails and stunning views from the top of the Giant, making it a favorite among outdoor enthusiasts.

The number of vacation rental properties in Cheshire is quite varied, offering options that cater to different preferences and budgets. Staying in this area allows you to enjoy the local charm while being conveniently located to explore nearby attractions and the beautiful Connecticut countryside.
How much does it cost to rent a vacation home in Cheshire?
Prices for vacation rentals in Cheshire 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 Cheshire 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 Cheshire vacation house rentals?
You can find great discounts on house rentals in Cheshire 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.
What is the most popular type of vacation rental accomodation in Cheshire?
In Cheshire, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These homes often feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups. Many vacation houses also come with outdoor spaces such as patios or gardens, great for enjoying the picturesque surroundings of Cheshire. Additionally, there are several cabins and apartments available, providing a range of options for visitors looking for a cozy getaway in this charming Connecticut town.
Are there any family house rentals in Cheshire?
In Cheshire, Connecticut, there are several family-friendly house rentals available, making it a great choice for groups looking to enjoy a comfortable stay. Visitors can find homes in neighborhoods close to local parks and recreational areas, providing ample opportunities for outdoor activities. Many of these properties feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas for kids to play.

Additionally, travelers will appreciate amenities such as Wi-Fi and air conditioning, ensuring a relaxing environment. The town also boasts nearby attractions, including charming shops and restaurants, making it easy to explore local culture.
Can I find long-stay vacation rentals in Cheshire?
A long-stay vacation rental in Cheshire 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 pet-friendly house rentals in Cheshire?
In Cheshire, there are several pet-friendly house rentals available, making it a great destination for travelers who want to bring their furry companions along. Many of these vacation homes come with amenities such as spacious backyards, which are ideal for pets to roam and play, as well as fully equipped kitchens for preparing meals. You can expect comfortable living areas, often with multiple bedrooms, suiting families or groups.

The town itself offers a charming suburban atmosphere, with access to local parks and outdoor spaces where pets are welcome. Nearby, the Cheshire Park features walking trails and open areas great for leisurely strolls with your dog. Additionally, some properties may be located close to pet-friendly cafes and shops, enhancing the overall experience for both guests and their pets.
Are there any remote work vacation rentals in Cheshire?
In Cheshire, Connecticut, there are several vacation rentals that cater to remote work needs. Many of these properties come equipped with essential amenities such as high-speed internet access and designated workspaces, including desks and comfortable chairs, providing an ideal environment for productivity. Travelers can expect free Wi-Fi in their accommodations, ensuring connectivity throughout their stay.

The town's suburban setting offers a peaceful atmosphere great for focusing on work while also providing access to local parks and recreational areas for breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cheshire vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cheshire 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 Cheshire?
In Cheshire, popular vacation rental amenities include onsite parking, which provides convenience for travelers with vehicles. Many rentals also feature decks or patios, allowing guests to enjoy outdoor space for relaxation or dining. A dedicated workspace with a desk caters to those who may need to attend to work while traveling. Additionally, many properties come equipped with fireplaces, creating a cozy atmosphere during cooler months. Lastly, kitchens are a standard amenity, enabling guests to prepare their own meals and enjoy the comforts of home.
When is the best time to visit Cheshire for a vacation rental?
The best time to visit Cheshire for a vacation rental is during the peak season from May to July, with July being particularly popular among travelers. This vibrant period welcomes families and adventure seekers, as the warm weather creates superb conditions for outdoor activities, including hiking and exploring local parks.

During these months, temperatures typically range from the mid-60s to the low 80s Fahrenheit, providing a comfortable climate for sightseeing and enjoying the lush landscapes. Cheshire's parks and natural spots are ideal for picnics or leisurely strolls, allowing guests to fully immerse themselves in the area's beauty.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter atmosphere, making it an excellent time to explore the charming town and its historical sites without the summer crowds. The fall season brings a unique charm, with beautiful autumn foliage enhancing the picturesque scenery.
How early should I book a Cheshire vacation rental?
Book your Cheshire 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 Cheshire, Connecticut, United States of America?
In Cheshire, visitors can enjoy a range of attractions that highlight the town's natural beauty and local charm. The Cheshire Hollow Farm offers a delightful experience for families, featuring a petting zoo and seasonal activities like pumpkin picking. The town's parks, such as Bartlem Park, provide walking trails, sports facilities, and picnic areas, making them ideal for outdoor enthusiasts. For those interested in history, the Cheshire Historical Society showcases local artifacts and exhibits that tell the story of the town's past. Additionally, the nearby Sleeping Giant State Park offers hiking trails with stunning views from the top of the giant's head, appealing to nature lovers and adventure seekers alike.
Can I change or cancel my Cheshire home rental booking on Vrbo?
To find Cheshire 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 Cheshire 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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