Chester holiday lettings

We found 1,573 holiday rentals — enter your dates for availability

Discover a selection of 33 homes and other holiday rentals in Chester that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as a fireplace and garden. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Chester

Showing deals for:26 Sept - 3 Oct
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Why visit Chester

  • Outdoor pursuits: Chester is perfect for skiing and adventure sports, set in picturesque countryside.
  • Charming local towns: Explore nearby historical towns known for their friendly locals and quaint vibes.
  • Varied accommodation options: Choose from private homes, cosy condos, and charming cabins for your stay.
  • Stunning national parks: Discover beautiful parks and scenic mountains for hiking and relaxation.
  • Family-friendly activities: Enjoy a range of attractions suitable for visitors of all ages.

Popular types of accommodation in Chester

If you're considering a getaway to Chester, you'll find a variety of delightful accommodation options to suit your needs. The most popular types of vacation rentals include houses, cosy condos, and charming cabins. Whether you're seeking private rentals in Chester or spacious house rentals, we have an array of available rentals to ensure you enjoy a memorable stay in this historic city.

  • Houses: The most sought-after option for holidaymakers in Chester, offering spacious and comfortable living for families and groups.
  • Condos: A popular choice, these self-contained units provide modern amenities and convenient access to local attractions.
  • Cabins: Ideal for a rustic getaway, these charming retreats often feature beautiful natural surroundings.
  • Apartments: A practical option for solo travellers or couples, providing a homely atmosphere in the heart of Chester.
  • Cottages: Quaint and cosy, these delightful spaces offer a true taste of country living.**

Top attractions in and around Chester

Chester, Vermont, is ideal for skiing and adventure sports, offering a variety of attractions for those seeking outdoor pursuits, cultural experiences, and family-friendly activities. The area boasts stunning national parks, scenic mountains, and lovely parks, making it a perfect destination for travellers looking to explore the great outdoors and enjoy a memorable holiday.

  • Lowell Lake State Park: Nestled 5.6km from Chester, this park offers stunning scenery and outdoor adventures, perfect for hiking, picnicking, and birdwatching amidst tranquil natural surroundings.
  • DaVallia Art & Accents: Located in the heart of Chester, this gallery showcases local art and crafts, providing a cultural experience that highlights the talents of regional artists in a charming setting.
  • Vermont Museum of Mining and Minerals: Situated 3.7km away, this family-friendly museum features fascinating exhibits on Vermont's mining history, making it an engaging stop for all ages.

Things to do recommended for couples

Chester, Vermont, offers delightful couple experiences. Enjoy skiing at Okemo Mountain Resort, only 6.8km away, or embark on an adventurous scenic flight at Morningside Flight Park, 7.5km from town. For a thrilling day, take the Sachem Ski Lift, also 7.5km away, and embrace the winter wonderland.

Things to do recommended for families

Families visiting Chester, Vermont, can have a fantastic time at Maple Lanes arcadeAdventureZone, just 8.7km away, enjoy ice skating at The Ice House recreationCentre, 8.1km away, and experience thrills on the Timber Ripper Mountain Coaster, also 8.1km from Chester.

Things to do recommended for groups

Groups visiting Chester, Vermont, can enjoy a trip to the Vermont Country Store, located 3.7km away, or catch a show at the Weston Playhouse, 6.2km distant. Don't miss the West River Farmers Market, 6.8km from Chester, for a taste of local culture and produce.

Booking with Vrbo is a breeze

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

Where to stay near Chester

Chester, Vermont, offers a delightful blend of adventure and relaxation for visitors. Nestled amidst the picturesque Cheshire countryside and rolling hills, it’s perfect for skiing and outdoor sports. Just a stone's throw away, explore charming nearby towns with their historical vibes and friendly locals. Whether you prefer the tranquillity of budget accommodation or the luxury of city centre lodgings, Chester promises an unforgettable holiday experience.

  • Ludlow: Situated 6.8km from Chester, Ludlow is a charming city renowned for its winter sports and outdoor adventures. The area attracts visitors for its exceptional skiing opportunities, with several ski fields and resorts nearby, making it a popular destination for thrill-seekers and sports enthusiasts alike. The scenic beauty of the surrounding landscape, including picturesque lakes, towering mountains, and serene valleys, adds to the allure. Whether you're carving down the slopes or enjoying a leisurely stroll by the lake, Ludlow offers a delightful experience for all adventurers.
  • Springfield: Just 3.7km from Chester, Springfield is another gem for those who love skiing and outdoor activities. This city is well-known for its access to ski resorts and fields that cater to all skill levels. The nearby national state park provides an excellent backdrop for hiking and exploration, ensuring that nature lovers have plenty to discover. With its beautiful lakes and mountainous terrain, Springfield offers a perfect blend of adventure and relaxation, making it a fantastic choice for a day trip.
  • Grafton: Located a mere 3.7km from Chester, Grafton is a quaint city that beckons outdoor enthusiasts and ski lovers. The area is celebrated for its ski fields and resorts, providing ample opportunities for winter sports. Surrounded by breathtaking valleys and mountains, Grafton serves as a gateway to splendid landscapes that are ideal for hiking and other outdoor pursuits. Visitors can enjoy the tranquil lakes and immerse themselves in the natural beauty that Grafton has to offer, ensuring a memorable experience for those seeking adventure in the great outdoors.

Best time to go to Chester

If you're planning a trip to Chester, 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 January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.7°F (-6.3°C)Light RainMostly CloudySlightly LowModerately High
February22.6°F (-5.2°C)Light RainMostly CloudySlightly LowModerately High
March30.7°F (-0.7°C)Light RainMostly CloudySlightly LowAverage
April42.8°F (6.0°C)Light RainMostly CloudyAverageModerately Low
May55.8°F (13.2°C)Light RainMostly SunnyAverageModerately Low
June63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
July69.3°F (20.7°C)Light RainMostly SunnySlightly HighAverage
August67.3°F (19.6°C)Light RainMostly SunnySlightly HighAverage
September60.3°F (15.7°C)Light RainMostly SunnySlightly HighModerately Low
October48.6°F (9.2°C)Light RainMostly SunnyAverageAverage
November36.1°F (2.3°C)Light RainMostly SunnyAverageAverage
December27.3°F (-2.6°C)Light RainMostly CloudyAverageModerately High

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

When travelling with a group, family, pets, or planning an extended stay, it's important to filter your options according to your key preferences. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chester 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 filter for these options and many others on Vrbo.
  • Traveling to Chester with young kids: Embarking on a journey with young children can present its own set of challenges. It’s essential to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Chester: For many families, a holiday wouldn't feel complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chester: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect destination. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or even a private pool to your criteria.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a dedicated space for you to craft new journeys, refine your plans, or manage your bookings with ease. The properties you’ve saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting cosy Chester

The mountains and surrounding scenery provide a peaceful ambience to your holiday home in Chester. This relaxing city is known for its hiking, skiing and coffee shops. 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 Chester

Are you searching for attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Chester a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Vermont Country Store (6.4 mi / 10.3 km)
  • Magic Mountain Ski Resort (9.7 mi / 15.6 km)
  • Viking Nordic Center (9.9 mi / 15.9 km)
  • Okemo Mountain Resort (11.4 mi / 18.3 km)
  • Fox Run Golf Course (11.8 mi / 19.1 km)
  • Stratton Mountain Golf Course (13 mi / 21 km)

Exploring the natural features in Chester

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Chester. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Lowell Lake State Park (9 mi / 14.5 km)
  • Buttermilk Falls (13.8 mi / 22.1 km)
  • Lake Rescue (14.1 mi / 22.7 km)
  • Mount Ascutney (14.4 mi / 23.1 km)
  • Winhall River (14.8 mi / 23.7 km)
  • Echo Lake (15.5 mi / 25 km)

Seasonal weather averages in Chester

Travellers enjoy Chester for its skiing. If you're interested in winter sports, you might consider visiting in January, March, November or February, when snowfall averages 35 cm and temperatures average -4°C.

Travelling to and around Chester

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 6.6 mi (10.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away.

Frequently asked questions

What is the best area to stay in Chester when booking a holiday rental?
If you're planning a holiday in Chester, Chester Depot is among the most sought-after locations to stay. No matter your style of travel, Vrbo is bound to have a holiday property here that's right for you.
What is the most popular type of holiday rental accommodation in Chester?
Houses are the most popular style of holiday rental in Chester, according to our data. Even if you have a different idea about what you want, Vrbo has properties in many shapes and sizes. Browse our options to find your ideal match.
How much does it cost to rent a holiday rental in Chester?
A number of factors can affect the price of a holiday rental in Chester, such as the type of property, length of stay and season. But, all of our holiday homes have one thing in common --- unbeatable value. Just add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Chester?
The average price for a holiday rental close to the beach in Chester will depend on when you're going and the type and size of property you're looking for. You can easily find prices on Vrbo by entering the dates you'll be travelling. Then use the filter tool to choose the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.
Are there pet-friendly holiday rentals in Chester?
Pack up a suitcase for the pooch in your life because Chester has 35 holiday rentals that throw open their doors to pets. Let your furriest pal join in with the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates then check our "Pets allowed" filter box.
Can I rent a house with a pool in Chester?
Pack your swimwear and inflatable flamingo, because there are six houses with a private pool in Chester. Unwind at one of these sought-after holiday rentals and let every day be a pool day. Simply enter your dates into Vrbo, then use the "pool" filter to find the ideal place for a splashing good time!
What are popular rental amenities in Chester?
A water view, ski-in/ski-out facilities and a sauna are rated the most popular rental amenities in Chester. Whether you're taking to the road by yourself, with your other half or a group of friends, Vrbo will help you find a holiday rental that matches your style with all the conveniences you're looking for.
Are there large group holiday rentals in Chester?
Chester has 11 holiday properties that can host 10 or more guests. These stays come with plenty of space to share good times with friends and family.
Are there holiday rentals in Chester that welcome kids?
Gather the whole crew for an adventure in Chester at one of our 35 family-friendly holiday properties. A lot of these stays come with amenities that are great for getaways with the little ones, like laundry facilities, extra bedrooms and patios. Simply click on the "Properties good for families" filter box and choose your favourite option.
What are the top attractions for families in Chester?
If you're seeking some fun for the whole family close to the heart of Chester, make sure to visit DaVallia Art & Accents.
Are there one-bedroom holiday rentals in Chester?
Yes, you can take your pick from five one-bedroom rentals in Chester. Whether you'd prefer a cosy chalet or a cabin, our one-bedroom properties are perfect if you don't require a huge amount of space. One of the major perks of having your own pad? You won't have to share your trip with strangers.
Can I find two-bedroom holiday rentals in Chester?
Take off with your besties and enjoy a relaxing escape in one of the four two-bedroom holiday properties Chester has to offer.
Are there holiday rentals with WiFi in Chester?
Take your pick of 21 holiday rentals with WiFi in Chester. If you want to disconnect from daily life during your trip, but still want to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Chester?
Chester has 20 holiday rentals where you can unwind in air-conditioned comfort. To locate a property on Vrbo that has this amenity, enter your travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Chester?
Age restrictions can differ across properties on Vrbo, so check the rules of the holiday rental in Chester you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Chester for?
The amount of time you can book a Chester holiday rental for is down to the property. Just tap in your preferred travel dates to view available options offering longer term stays. They include everything you need to make your extended getaway more comfortable like kitchens and air conditioning. Some properties may also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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