Chester Accommodations

Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required

Highly Rated

10.0

Exceptional

(241 Reviews)

Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required

4 Guests 2 Bedrooms 1 Bathroom

Family Friendly House

Fireplace/Heating
Balcony/Terrace
Pet Friendly

AU $196/Night For 7 Nights AU $1,375

View Deal

9.7

Exceptional

(73 Reviews)

Franklyn Farm Inn

247.57 ft² 6 Guests 2 Bedrooms 2 Bathrooms

Bed & Breakfast

Fireplace/Heating
Balcony/Terrace
View

AU $225/Night For 7 Nights AU $1,572

View Deal

Highly Rated

9.2

Exceptional

(118 Reviews)

Stone Hearth Inn and Eatery

1 Bedroom 1 Bathroom

Family Friendly Bed & Breakfast

Fireplace/Heating
Balcony/Terrace
Breakfast

AU $391/Night For 7 Nights AU $2,736

View Deal

Vermont Charm in the 1840 Gideon Lee House

10.0

Exceptional

(29 Reviews)

Vermont Charm in the 1840 Gideon Lee House

1500 ft² 6 Guests 2 Bedrooms 1 Bathroom

Family Friendly House

Fireplace/Heating
Balcony/Terrace
Kitchen

AU $387/Night For 7 Nights AU $2,706

View Deal

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

9.7

Exceptional

(3 Reviews)

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

742.71 ft² 4 Guests 2 Bedrooms 1 Bathroom

Free Cancellation House

Fireplace/Heating
Pet Friendly
Parking

AU $340/Night For 7 Nights AU $2,377

View Deal

Sage House at Camp Greenwood Vermont with Sauna

10.0

Exceptional

(5 Reviews)

Sage House at Camp Greenwood Vermont with Sauna

275 ft² 2 Guests 1 Bedroom 1 Bathroom

Family Friendly Cabin

Fireplace/Heating
Balcony/Terrace
Pet Friendly

AU $323/Night For 7 Nights AU $2,259

View Deal

9.5

Exceptional

(2 Reviews)

Sage House at Camp Greenwood Vermont with Sauna

279.86 ft² 2 Guests 1 Bedroom 1 Bathroom

Free Cancellation House

Fireplace/Heating
View
Pet Friendly

AU $374/Night For 7 Nights AU $2,620

View Deal

Thistle House at Camp Greenwood Vermont with Sauna

10.0

Exceptional

(1 Review)

Thistle House at Camp Greenwood Vermont with Sauna

275 ft² 2 Guests 1 Bedroom 1 Bathroom

Family Friendly Cabin

Fireplace/Heating
Balcony/Terrace
Pet Friendly

AU $313/Night For 7 Nights AU $2,192

View Deal

8.7

Fabulous

(79 Reviews)

Stone Hearth Inn and Eatery

16 Guests 7 Bedrooms 7 Bathrooms

Family Friendly Bed & Breakfast

Skiing
Fireplace/Heating
Balcony/Terrace

AU $325/Night For 7 Nights AU $2,276

View Deal

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!

Highly Rated

9.8

Exceptional

(73 Reviews)

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!

650 ft² 5 Guests 1 Bedroom 1 Bathroom

Family Friendly Cabin

Fireplace/Heating
Pool
Balcony/Terrace

AU $365/Night For 7 Nights AU $2,554

View Deal

8.0

Excellent

(1 Review)

Kingdom Valley Farmhouse

1797.57 ft² 6 Guests 1 Bedroom 1 Bathroom

Family Friendly House

Skiing
Fireplace/Heating
Balcony/Terrace

AU $630/Night For 7 Nights AU $4,413

View Deal

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

9.8

Exceptional

(24 Reviews)

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

500 ft² 4 Guests 2 Bedrooms 1 Bathroom

Family Friendly Cabin

Fireplace/Heating
Pet Friendly
Kitchen

AU $218/Night For 7 Nights AU $1,530

View Deal

More Top-Rated Accommodations in Chester Area

Why Choose Rent By Owner for your Chester Accommodations?

What makes our Accommodations special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Chester Accommodations

Where are the best neighborhoods to stay in Chester?

For an authentic Vermont experience, consider staying in neighborhoods around Chester that offer a charming blend of rural tranquility and easy access to local amenities. These areas provide a peaceful setting while remaining close to the heart of Chester, making it convenient to explore the scenic landscapes and nearby attractions. Whether you prefer a cozy retreat or a spacious property, selecting a neighborhood in this region ensures a comfortable and memorable stay in Vermont.

Chester Depot

Situated within the area, Chester Depot offers a convenient base for exploring the region’s charming surroundings. You'll find this neighborhood to be an ideal spot for easy access to local amenities and picturesque scenery.

View 47+ Rentals in Chester Depot

Best Times to Visit Chester

When should you plan your Accommodations stay?

Choosing the optimal time to vacation here ensures you experience the region's unique charm and natural beauty at its best, allowing you to enjoy your stay in Chester, Vermont, USA, whether you're seeking vibrant seasons or tranquil periods.

Peak Season Highlights

Summer (June to August)

During the warm summer months, the area experiences lively activity and ideal weather for outdoor pursuits, making it a popular time to visit this destination.

Average Temperature Daytime: Around 75°F to 85°F - Nighttime: Approximately 55°F to 65°F

Fall (September to November)

The vibrant foliage and crisp air attract visitors seeking the scenic beauty of the region during these months, creating a bustling atmosphere.

Average Temperature Daytime: Typically 60°F to 70°F - Nighttime: Cooling down to 40°F to 50°F

Off-Season Highlights

Winter (December to February)

Colder weather and fewer visitors characterize this period, offering a peaceful retreat for those looking to enjoy the quiet charm of the area.

Average Temperature Daytime: Between 20°F and 35°F - Nighttime: Often below freezing, around 10°F to 25°F

Spring (March to May)

As nature awakens, fewer travelers arrive here, providing a tranquil environment perfect for exploring at your own pace.

Average Temperature Daytime: Ranging from 45°F to 60°F - Nighttime: About 30°F to 45°F

Weekly Weather Forecast for Chester

How to Book Your Chester Accommodations

What's our booking process?

Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Chester

More Top-Rated Accommodations in Chester Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

You can enjoy a spacious outdoor patio or deck, perfect for relaxing and taking in the scenic views.
Many rentals feature access to private or shared gardens where you can unwind amidst lush greenery.
Look for outdoor dining areas that allow you to savor meals alfresco during your stay.
Expect well-maintained lawns or yards for outdoor activities or simply enjoying the fresh air.
Some accommodations include outdoor fire pits, ideal for evening gatherings with family or friends.
Experience easy access to nearby hiking trails or nature walks directly from the property.
Outdoor parking facilities are commonly available to ensure convenience during your visit to the region.

Top Attractions Around Chester

What attractions are nearby?

While staying here, you can explore a variety of outdoor activities such as hiking, biking, and fishing in the scenic landscapes surrounding Chester, Vermont, making it an ideal destination for nature enthusiasts seeking a relaxing yet adventurous escape in this charming region.

Family Activities

Chester Depot Explore the historic Chester Depot, where families can enjoy scenic train rides and learn about the area's railroad history in a fun, educational setting.
Hapgood Pond Spend quality time at Hapgood Pond by swimming, picnicking, or paddling around the peaceful waters, perfect for outdoor family activities in this charming region.
The Vermont Country Store Discover unique local products and enjoy interactive demonstrations that make shopping an engaging experience for children and adults alike.
Okemo Mountain Resort Experience year-round adventures such as skiing and snowboarding during winter or hiking and mountain biking in the warmer months, ideal for active families visiting here.

Adult Activities

Hiking and Nature Walks: Explore the scenic trails and outdoor pathways that showcase the natural beauty of Chester, Vermont, providing a peaceful escape into the region’s lush landscapes.
Visiting Local Art Galleries and Studios: Discover vibrant art scenes by browsing through galleries and studios that highlight the creative talents unique to this destination.
Enjoying Gourmet Dining Experiences: Savor farm-to-table cuisine at acclaimed restaurants that emphasize the fresh, local ingredients typical of the area.
Relaxing at Spa and Wellness Centers: Unwind with rejuvenating spa treatments and wellness services designed to enhance your visit to this idyllic Vermont locale.

Other Places to Stay in Chester, VT

DaVallia Art & Accents

Explore 60 Properties

Bonnie's Bundles Dolls

Explore 60 Properties

Chester Depot

Explore 47 Properties

More Places to Stay Near Chester

Chester Travel Tips

How Can You Make the Most of Your Stay?

Explore local outdoor activities: Take advantage of the area's scenic trails and outdoor adventures to fully immerse yourself in the natural beauty of this destination.
Visit charming small-town shops: Discover unique handcrafted items and local specialties by strolling through the quaint shops that line the streets here.
Plan a day trip to nearby attractions: Use this opportunity to explore surrounding sites, ensuring you experience all that the region has to offer beyond your accommodations.
Sample regional cuisine: Enjoy authentic local flavors at nearby eateries, making your stay even more memorable through delicious culinary experiences.

Transportation Options

Chester Airport: You can easily access the area through this regional airport, offering convenient flights for travelers arriving from various locations.
Taxi Services: Reliable taxi companies operate within the region, providing comfortable and direct transportation options around Chester and nearby destinations.
Car Rentals: Numerous car rental agencies are available here, giving you the flexibility to explore the scenic surroundings at your own pace.
Public Transit: Local bus services connect key points within the region, offering an affordable way to travel around without the need for a personal vehicle.

Local Customs Options

Chester's Maple Syrup Tradition: You can experience the region's rich heritage by exploring local maple syrup production, a beloved custom that symbolizes Vermont's agricultural roots.
Community Fall Festivals: Participating in seasonal festivals here allows you to enjoy local crafts, foods, and entertainment rooted in longstanding regional customs.
Vermont Folk Music Engaging with traditional folk music sessions provides insight into the area's cultural history and is a cherished practice among residents.
Local Artisanal Markets: Visiting markets filled with handcrafted goods supports regional artisans and offers a glimpse into the area's artistic traditions.

Frequently Asked Questions about Chester Accommodations

1. What are the top Accommodations in Chester?

There are a lot of options in Chester. If you plan on staying in the Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Accommodations in Chester:

2. How many Accommodations are available in Chester?

Currently, the total number of properties listed by RBO in 2026 is over 82 in the Chester area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Chester. 

3. What is the cancellation policy for accommodations in Chester, Vermont?

Cancellation policies can vary depending on the specific property you choose. It’s recommended to review the individual listing details or contact the property owner directly to understand the terms and any potential fees.

4. Are there any specific check-in and check-out times I should be aware of during my stay in this region?

Check-in and check-out times are set by each property. Details are typically provided within the listing, so be sure to review these when booking or reach out to the host for clarification.

5. How do I find accommodations that are pet-friendly in Chester, Vermont?

Pet-friendly options are available but not universal. Use the filtering tools on the booking site to narrow your search to properties that welcome pets, and consult the property description or contact the owner for confirmation.

6. What amenities are typically included in accommodations here?

Amenities vary across listings, but common features include Wi-Fi, parking, kitchen facilities, and indoor heating. Check each property’s listing for a complete list of available amenities.

7. Is there a way to secure special rates or discounts for longer stays?

Special rates for extended stays may be offered. Review the listing details for any promotion information or contact the property owner directly to inquire about discounts for longer bookings.