Chester Depot vacation rentals

We found 22 vacation rentals — enter your dates for availability

Discover a selection of 10 homes and other vacation rentals in Chester Depot that are perfect for your trip. Vacation rentals provide the amenities you need and want for your stay with friends, family, or just your pet, such as parking and a fireplace. What you'll find is a rental for everyone's needs, including options that are accessible or non-smoking.

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Find out more about Chester Depot

Why visit Chester Depot

  • Outdoor Adventures: Chester Depot is ideal for outdoor enthusiasts, offering skiing, hiking, and exploration of local and state parks.
  • Historic Charm: Discover the rich history of Chester Depot, including the Chester Depot Museum and the Chester Historical Society.
  • Unique Architecture: Explore the picturesque Stone Village, known for its unique architectural styles that reflect the town's heritage.
  • Quaint Downtown: Enjoy the friendly atmosphere of historic downtown Chester, complete with charming shops and local culture.
  • Cozy Accommodations: Choose from budget-friendly vacation rentals, including cabins and condos, for a comfortable stay.

Popular types of accommodation around Chester Depot

Discover the charm of Chester Depot, where you can find the perfect vacation rental for your getaway. Our most popular accommodations include Houses, Condos, and cozy Cabins. Enjoy the convenience of free parking and experience the unique character of places like St. James Place and Winkler Place, all while being close to the historic train depot in Vermont. Your ideal retreat awaits.

  • Houses: The top choice for travelers in Chester Depot, offering spacious and comfortable living for families or groups.
  • Condos: A favored option, providing modern amenities and a convenient location for exploring the area.
  • Cabins: A popular selection for those seeking a rustic experience surrounded by nature.
  • Apartments: A practical choice for couples or solo travelers looking for a cozy stay.
  • Chalets: A charming option that combines comfort with a picturesque alpine vibe.**

Top attractions in and around Chester Depot

Chester Depot, Vermont, is perfect for outdoor enthusiasts seeking skiing and adventure. Visitors can explore local parks, national and state parks, and the Chester Depot Museum for a taste of history. This charming destination offers a blend of culture and family-friendly experiences, making it an ideal spot for travelers looking to connect with nature and local heritage. Don't miss the Chester Historical Society for even more insights into the area's rich past.

  • DaVallia Art & Accents: This charming gallery in Chester Depot offers a unique cultural experience with an array of local art and handcrafted items. The vibrant atmosphere invites you to explore the creativity of regional artists, making it a perfect spot for art lovers and collectors.
  • Bonnie's Bundles Dolls: A delightful attraction filled with enchanting dolls that evoke a sense of nostalgia and romance. This quaint shop is perfect for those seeking a unique keepsake or a glimpse into the artistry of doll-making.
  • Lowell Lake State Park: Located 9 miles from Chester Depot, this stunning park is a haven for outdoor enthusiasts. With its beautiful scenery, hiking trails, and opportunities for adventure, it’s an ideal spot for nature lovers to unwind and explore.

Things to do recommended for couples

For a romantic getaway in Chester Depot, consider skiing at Okemo Mountain Resort, taking a scenic flight at Morningside Flight Park, or enjoying an adventure on the South Face Express Ski Lift. Each offers breathtaking views and exhilarating experiences perfect for couples.

Things to do recommended for families

Families visiting Chester Depot can enjoy ice skating at The Ice House, located 13 miles away, or have a blast at Maple Lanes Arcade, 14 miles away. For adventure seekers, the Timber Ripper Mountain Coaster, also 13 miles away, offers thrilling fun for everyone.

Things to do recommended for groups

Experience local charm at the Vermont Country Store, just 6 miles from Chester Depot. Enjoy a captivating performance at the Weston Playhouse, 10 miles away, or hit the links at Fox Run Golf Course, 12 miles away, for some outdoor fun with your group.

*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 around Chester Depot

If you're planning a trip with friends, family, pets, or extended stays, be sure to prioritize your search accordingly. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Chester Depot 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 these options and more on Vrbo.
  • Traveling to Chester Depot with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Chester Depot: For many families, a vacation wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Chester Depot: 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 rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Chester Depot

Chester Depot, Vermont, is a charming destination perfect for adventure seekers and outdoor enthusiasts. Explore the historic downtown Chester, with its quaint shops and friendly atmosphere. Don’t miss the picturesque Stone Village, showcasing unique architecture, or the rich history of this former railroad town. With its budget-friendly accommodations and relaxing vibes, Chester Depot offers a delightful escape into Vermont's natural beauty and heritage.

  • Chester: Chester is a charming town nestled in the heart of Vermont, with Chester Depot serving as a quaint hub for visitors. Known for its picturesque landscapes and outdoor adventures, Chester offers a plethora of activities, especially for skiing enthusiasts. The town is surrounded by stunning mountains, valleys, and lakes, making it an ideal spot for sports and adventure seekers. In the winter, visitors flock to nearby ski resorts for thrilling slopes, while the summer invites exploration of hiking trails and scenic viewpoints. Chester’s historic charm can also be appreciated through its local shops and eateries, providing a delightful backdrop for your vacation.
  • Ludlow: Located 11 miles from Chester Depot, Ludlow is another gem in Vermont’s ski country. This vibrant town is a favorite among travelers looking for both adventure and relaxation. With its proximity to major ski resorts, Ludlow is a hotspot for winter sports, offering a variety of slopes for all skill levels. The surrounding natural beauty, including lakes and mountains, provides ample opportunities for hiking, fishing, and exploration year-round. Ludlow also features a lively downtown area with shops, restaurants, and a welcoming community vibe, ensuring a fulfilling travel experience.
  • Springfield: Just 6 miles from Chester Depot, Springfield is a delightful city that blends outdoor adventure with cultural experiences. Like its neighboring towns, Springfield is popular for skiing and sports, drawing visitors to its nearby ski fields and resorts. The city is also home to natural attractions such as picturesque lakes and the stunning national state park, which offers hiking trails and wildlife viewing. Springfield boasts a rich history and vibrant community, making it a wonderful place to discover local art, dining, and traditions, ensuring a well-rounded vacation experience.

Best time to go to Chester Depot

If you're planning a trip to Chester Depot, it's a good idea to check both the weather and property rates. The warmest months are July and July. Peak season runs in January to February, February, December to January and December, while off-peak times, like April, April to May, May, November and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.7°F (-6.3°C)Light RainMostly CloudyHighModerately High
January20.7°F (-6.3°C)Light RainMostly CloudyHighModerately High
February22.6°F (-5.2°C)Light RainMostly CloudyHighModerately High
February22.6°F (-5.2°C)Light RainMostly CloudyHighModerately High
March30.7°F (-0.7°C)Light RainMostly CloudyAverageAverage
March30.7°F (-0.7°C)Light RainMostly CloudyAverageAverage
April42.8°F (6.0°C)Light RainMostly CloudyLowModerately Low
April42.8°F (6.0°C)Light RainMostly CloudyLowModerately Low
May55.8°F (13.2°C)Light RainMostly SunnyLowModerately Low
May55.8°F (13.2°C)Light RainMostly SunnyLowModerately Low
June63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
June63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
July69.3°F (20.7°C)Light RainMostly SunnyAverageAverage
July69.3°F (20.7°C)Light RainMostly SunnyAverageAverage
August67.3°F (19.6°C)Light RainMostly SunnyAverageAverage
August67.3°F (19.6°C)Light RainMostly SunnyAverageAverage
September60.3°F (15.7°C)Light RainMostly SunnyAverageModerately Low
September60.3°F (15.7°C)Light RainMostly SunnyAverageModerately Low
October48.6°F (9.2°C)Light RainMostly SunnyAverageAverage
October48.6°F (9.2°C)Light RainMostly SunnyAverageAverage
November36.1°F (2.3°C)Light RainMostly SunnyLowAverage
November36.1°F (2.3°C)Light RainMostly SunnyLowAverage
December27.3°F (-2.6°C)Light RainMostly CloudyHighModerately High
December27.3°F (-2.6°C)Light RainMostly CloudyHighModerately High

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to 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 needs.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner truly has its rewards. When you sign up for our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on eligible bookings. Join us today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly area to plan new trips, resume your previous plans, or organize your travel itinerary. You'll easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Chester Depot?
In Chester Depot, vacation houses are the most popular type of vacation rental, with several available in picturesque settings. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and cozy living areas, making them great for families or groups. Many rentals come with outdoor spaces such as decks or patios, allowing guests to enjoy the serene Vermont landscape.
How much does it cost to rent a vacation home in Chester Depot?
Prices for vacation rentals in Chester Depot 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 Chester Depot 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 Chester Depot vacation house rentals?
You can find great discounts on house rentals in Chester Depot 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 are popular rental amenities in Chester Depot?
In Chester Depot, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals during their stay. Many rentals also feature appliances like blenders and coffee/tea makers, enhancing the convenience of home-cooked breakfasts or snacks. Outdoor spaces, such as decks or patios, are common as well, providing guests with areas to relax and enjoy the natural surroundings. Additionally, electric kettles are often available for those who appreciate a warm beverage at any time.
Are there any family house rentals in Chester Depot?
In Chester Depot, Vermont, there are several family-friendly house rentals available, offering a variety of options for travelers. The area is known for its beautiful landscapes and proximity to outdoor activities, making it a great choice for families seeking adventure. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals, and cozy spaces for relaxation after a day of exploring.

Families can enjoy nearby attractions such as the scenic Okemo Mountain Resort, which offers skiing in the winter and hiking in the summer. The charming local community also provides opportunities for shopping and dining, with quaint stores and eateries that showcase the region's hospitality.
Can I rent a vacation home with a pool or hot tub in Chester Depot?
In Chester Depot, Vermont, travelers will find several vacation homes available for rent that come with pools or hot tubs. This charming area offers a picturesque setting ideal for relaxation and outdoor activities. Many of these properties are equipped with private pools, inviting hot tubs, and spacious outdoor areas great for enjoying the serene landscape. Inside, guests can expect comfortable living spaces, fully equipped kitchens, and cozy fireplaces, adding to the homey atmosphere.
Are there any Chester Depot vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chester Depot 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.
Are there pet-friendly vacation rentals in Chester Depot?
In Chester Depot, Vermont, there are several pet-friendly vacation rentals available for travelers. This charming area offers a mix of rustic cabins and cozy cottages, many of which come equipped with amenities such as fully functional kitchens, outdoor decks, and comfortable living spaces designed for relaxation. Some properties may even feature hot tubs or fireplaces, great for unwinding after a day of exploring the beautiful Vermont landscape.

The surrounding region is rich in outdoor activities, making it an ideal destination for pet owners. Nearby, you can explore the scenic Green Mountain National Forest, which provides ample opportunities for hiking and enjoying nature with your furry companions. Additionally, the quaint town of Chester features local shops and eateries that welcome pets, enhancing the overall experience for travelers with pets.
Can I find long-stay vacation rentals in Chester Depot?
A long-stay vacation rental in Chester Depot 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 Chester Depot?
In Chester Depot, Vermont, there are several vacation rentals available that cater to remote work needs. These accommodations often feature dedicated workspaces with desks and comfortable chairs, allowing for a productive work environment. Travelers can expect amenities such as high-speed Wi-Fi, which is essential for staying connected, and many rentals also offer cozy living spaces superb for unwinding after a day of work.

The area itself is picturesque, surrounded by the scenic Green Mountains, providing a peaceful backdrop for remote work. Additionally, there are opportunities for outdoor activities after hours, including hiking and exploring the charming local shops and eateries in Chester Depot. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Chester Depot vacation rental?
Book your Chester Depot 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 Chester Depot?
In Chester Depot, visitors can enjoy a quaint, small-town atmosphere with a variety of attractions. The historic downtown area features charming shops and local eateries, great for a leisurely stroll. Nearby, the scenic Green Mountain National Forest offers opportunities for hiking, mountain biking, and enjoying nature.

For a dose of local history, the Chester Historical Society and the picturesque Chester Village Green are worth exploring. Additionally, outdoor enthusiasts can take advantage of the nearby Okemo Mountain Resort for skiing in the winter or mountain activities in the warmer months.
Can I change or cancel my Chester Depot home rental booking on Vrbo?
To find Chester Depot 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 Chester Depot 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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