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Cheshire holiday lettings

We found 247 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Cheshire to find one that's perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, including parking and a garden. What you'll find is a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Cheshire

Showing deals for:17 Oct - 24 Oct

Why visit Cheshire

  • Charming countryside: Explore the picturesque landscapes and rural cottages that define Cheshire's scenic beauty.
  • Historical landmarks: Discover the rich local history through its notable sites and historic colleges.
  • Family-friendly activities: Enjoy a variety of engaging activities suitable for all ages, perfect for family outings.
  • Urban parks: Relax in delightful parks, ideal for picnics and enjoying the outdoors.
  • Welcoming accommodation: Choose from cosy cottages and spacious holiday homes for a comfortable stay.

Popular types of accommodation in Cheshire

Discover the charm of Cheshire with our selection of holiday cottages, houses, and apartments. Whether you're seeking a cozy cottage for a romantic getaway or a spacious rental for a family holiday, we have the perfect accommodation for you. Explore the best Cheshire cottages that offer transparency and savings, ensuring a delightful stay in this picturesque region.

  • Houses: The top choice for visitors in Cheshire, these homes offer a spacious and comfortable retreat for families, couples, or groups.
  • Cottages: Charming and often set in picturesque surroundings, cottages provide a quaint and cosy accommodation option.
  • Apartments: Ideal for those seeking a self-catering experience, apartments offer convenience and flexibility during your stay.
  • Condos: These modern accommodations are perfect for travellers wanting amenities and a community atmosphere.
  • Villas: Luxurious and spacious, villas offer a high-end lodging experience with plenty of room to relax.**

Top attractions near Cheshire

Cheshire, Connecticut, offers a delightful blend of family-friendly activities, cultural experiences, and outdoor adventures. Visitors can explore urban parks, historic colleges and universities, and national or state parks, making it an ideal destination for those seeking a relaxing yet enriching holiday. Whether you're enjoying a picnic in the park or learning about local history, Cheshire has something to captivate every traveller.

  • Quinnipiac University: This historic university offers a rich cultural experience with its beautiful campus and vibrant student life. Visitors can explore its impressive architecture and enjoy various cultural events throughout the year.
  • Choate Rosemary Hall: A prestigious modern school located in a vibrant city setting, it boasts striking contemporary facilities and a dynamic atmosphere, making it an intriguing place for anyone interested in education and innovation.
  • Lake Compounce: As the oldest amusement park in the United States, it provides a fantastic family-friendly environment filled with thrilling rides, outdoor adventures, and seasonal events for all ages.

Things to do recommended for couples

Cheshire offers charming experiences for couples. Enjoy skiing at Powder Ridge Mountain Park, indulge in a wine tasting at Gouveia Winery, or engage in friendly competition at Putter's Paradise Mini Golf. Each location, a short drive away, promises a delightful mix of romance and adventure.

Things to do recommended for families

During your family vacation in Cheshire, Connecticut, enjoy the serene wellness vibes at Hubbard Park, engage in sports at Falcon Field, and embark on thrilling adventures at Crystal Bees arcade. Each location offers unique experiences perfect for creating lasting family memories.

Things to do recommended for groups

Experience a captivating show at the Toyota Oakdale Theatre, just 3.1km from Cheshire. Enjoy shopping at Maplecroft Plaza in town, or visit the Brass Mill Center 4.3km away for a blend of entertainment and family fun. Perfect for creating cherished memories with your group!

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Cheshire

Cheshire, Connecticut, offers a delightful blend of family-friendly activities and charming countryside escapes. Explore the picturesque Cheshire town with its historical landmarks, or venture into the beautiful Cheshire countryside, where rural cottages and scenic views await. With a welcoming atmosphere and a rich cultural vibe, visitors can relish in both romantic strolls and family outings, making it an ideal destination for a memorable vacation.

  • Meriden: Located a mere 3.7km from Cheshire, Meriden is a vibrant city that offers a delightful mix of family-friendly activities and cultural experiences. Visitors can explore the local theatre scene or enjoy a round of golf at one of the area's well-maintained courses. Meriden's attractions also include a historic college university that adds an educational dimension to your visit. Don't miss the chance to visit the nearby theme park, perfect for a day of fun and excitement with family.
  • Waterbury: Situated 4.3km from Cheshire, Waterbury is known for its adventurous spirit and outdoor activities. This bustling city is perfect for families looking to create lasting memories. Explore the educational venues or unwind at a local resort. The area is home to an amusement park and a waterpark, making it an ideal spot for thrill-seekers and those wishing to cool off during hot days. Waterbury is a city that promises a lively experience for all ages.
  • Wallingford: Just 3.7km from Cheshire, Wallingford is a charming city that combines cultural attractions with romantic settings, perfect for families and couples alike. The local theatre scene provides entertainment, while the golf courses offer a leisurely day outdoors. Visitors can appreciate the historic college university nearby, which enhances the cultural vibe of the area. Wallingford also boasts an event conference venue and a modern college university, making it a hub of activity and learning.

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

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

If you're travelling with a group, family, pets, or planning an extended stay, it's important to refine your search according to your specific needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Cheshire with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all of these options, and more, on Vrbo.
  • Traveling to Cheshire with young kids: Travelling with young children can indeed be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it would be wise to think about your closeness to attractions that are suitable for families.
  • Taking your pets with you to Cheshire: For many, a family holiday isn't truly fulfilled without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Cheshire: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly area to plan new journeys, continue from where you paused, or review and arrange your travel plans. You'll discover the properties you’ve saved or booked neatly sorted into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/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 searching for things to do in the area? Venture out of your cosy holiday rental and experience everything that Cheshire has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mount Southington Ski Area (5.1 mi / 8.3 km)
  • Laurel View Country Club (7.8 mi / 12.6 km)
  • Powder Ridge Mountain Park and Resort (8.8 mi / 14.2 km)
  • Lake Compounce (9 mi / 14.5 km)
  • Hawks Landing Country Club (9.7 mi / 15.6 km)
  • Putter's Paradise Mini Golf (10.4 mi / 16.7 km)

Exploring the natural features in Cheshire

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Cheshire is a great place to spend some time outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Hubbard Park (5.1 mi / 8.3 km)
  • Mount Carmel (5.8 mi / 9.4 km)
  • Lake Beseck Beach (9.1 mi / 14.7 km)
  • Wadsworth Falls State Park (11.7 mi / 18.9 km)
  • East Rock Park (12.6 mi / 20.3 km)
  • New Haven Green (13.9 mi / 22.3 km)

Transport to and around Cheshire

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 12 mi (19.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is 16.5 mi (26.6 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Cheshire?
The most sought-after types of holiday rentals in Cheshire are houses. Hoping for something different? Vrbo has many options to match the diverse needs of our guests, so you'll see properties in all sizes, and for all budgets. The ideal fit is ready and waiting for you --- discover yours today.
How much does it cost to rent a holiday rental in Cheshire?
Property type, season and length of stay are some factors that can influence the price of a holiday home. Simply enter your dates of travel to find your perfect match. From comfy cabins to sprawling luxury villas, all Vrbo holiday rentals offer incredible value.
How much does it cost to rent a beach house in Cheshire?
When you travel and the style and size of the property will determine the cost of your beachside holiday rental. Click on your Cheshire travel dates to see all your options on Vrbo. Did someone just say "hot tub"? Use our filters to choose the features and amenities you want in your holiday home.
What are popular rental amenities in Cheshire?
Some of the most popular rental amenities guests are looking for in Cheshire are a fireplace, off-street parking options and a dishwasher. Whether you're on the road with buddies, family or even pets, Vrbo holiday homes come with the best amenities for fun and relaxation with the people that matter most.
What are the top attractions for families in Cheshire?
Keep the kids happy at these fun family-friendly attractions in Cheshire:

  • Lake Compounce
  • Lake Beseck Beach
  • Cheshire Hollow Farm

How old do you have to be to rent a holiday rental in Cheshire?
The minimum age requirements can vary across properties on Vrbo, so be sure to look at the rules of the holiday rental in Cheshire you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Cheshire for?
The length of time you can book a holiday rental in Cheshire is down to the property. Simply enter your selected travel dates to display a list of options offering extended stays. With loads of features like kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get a perfect place to call your home away from home in Cheshire.

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