Best Vacation Homes in Chester
House
10.0(243 Reviews)
2 Bedrooms
1 Bath
4 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $155/Night
7 Nights - US $1,082
Bed & Breakfast
9.7(73 Reviews)
2 Bedrooms
2 Baths
6 Guests
247.57 ft²
- Fireplace/Heating
- Balcony/Terrace
View
Parking
US $160/Night
7 Nights - US $1,120
Bed & Breakfast
9.2(118 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
US $213/Night
7 Nights - US $1,488
House
10.0(30 Reviews)
2 Bedrooms
1 Bath
6 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $271/Night
7 Nights - US $1,895
House
9.7(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
742.71 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
Internet
US $242/Night
7 Nights - US $1,694
Cabin
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
275 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $230/Night
7 Nights - US $1,610
Cabin
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
275 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $255/Night
7 Nights - US $1,782
Cabin
9.8(73 Reviews)
1 Bedroom
1 Bath
5 Guests
650 ft²
- Fireplace/Heating
Pool- Balcony/Terrace
- Kitchen
US $260/Night
7 Nights - US $1,820
Chester Luxury Rentals
House
10.0(1 Review)
6 Bedrooms
4 Baths
12 Guests
3000 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $1,074/Night
7 Nights - US $7,518
House
3 Bedrooms
2 Baths
10 Guests
2400.35 ft²
Hot Tub- Balcony/Terrace
- Pet Friendly
- Kitchen
US $925/Night
7 Nights - US $6,475
House
10.0(16 Reviews)
6 Bedrooms
3 Baths
8 Guests
3400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $740/Night
7 Nights - US $5,181
House
4 Bedrooms
2 Baths
12 Guests
- Balcony/Terrace
- Parking
Air Conditioner- Internet
US $719/Night
7 Nights - US $5,034
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1551 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $534/Night
7 Nights - US $3,736
House
5 Bedrooms
4 Baths
8 Guests
4500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $517/Night
7 Nights - US $3,621
House
10.0(10 Reviews)
5 Bedrooms
6 Baths
12 Guests
5000 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $510/Night
7 Nights - US $3,570
House
9.6(4 Reviews)
5 Bedrooms
2 Baths
8 Guests
2152 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $508/Night
7 Nights - US $3,557
Chester Pet Friendly Vacation Rentals
Cabin
9.8(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
500 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $156/Night
7 Nights - US $1,090
House
9.5(2 Reviews)
1 Bedroom
1 Bath
2 Guests
279.86 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $267/Night
7 Nights - US $1,867
House
9.8(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
738 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $205/Night
7 Nights - US $1,437
House
5 Bedrooms
2 Baths
10 Guests
3003.13 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $296/Night
7 Nights - US $2,072
Ski Chalet
10.0(11 Reviews)
4 Bedrooms
1 Bath
8 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $342/Night
7 Nights - US $2,394
Cabin
10.0(3 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $319/Night
7 Nights - US $2,234
House
9.8(51 Reviews)
5 Bedrooms
2 Baths
10 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $294/Night
7 Nights - US $2,056
House
9.4(22 Reviews)
4 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $409/Night
7 Nights - US $2,862
Chester Large Vacation Homes
Ski Chalet
10.0(8 Reviews)
5 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $494/Night
7 Nights - US $3,457
Bed & Breakfast
8.8(73 Reviews)
7 Bedrooms
7 Baths
16 Guests
Skiing- Fireplace/Heating
- Balcony/Terrace
- View
US $232/Night
7 Nights - US $1,622
House
10.0(3 Reviews)
6 Bedrooms
3 Baths
12 Guests
5000 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $830/Night
7 Nights - US $5,810
Other
4 Bedrooms
2 Baths
10 Guests
- Spa
- Fireplace/Heating
- Kitchen
- Parking
US $333/Night
7 Nights - US $2,328
House
10.0(41 Reviews)
5 Bedrooms
3 Baths
9 Guests
2700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $343/Night
7 Nights - US $2,399
House
9.8(8 Reviews)
5 Bedrooms
3 Baths
13 Guests
2564 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $583/Night
7 Nights - US $4,080
House
5.0(2 Reviews)
4 Bedrooms
2 Baths
11 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $425/Night
7 Nights - US $2,975
Other
5.0(1 Review)
5 Bedrooms
2 Baths
10 Guests
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
US $258/Night
7 Nights - US $1,806
Why Choose Rent By Owner for your Chester Vacation Rental Homes?
What makes our Vacation Rentals 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 Vacation Rentals
Where are the best neighborhoods to stay in Chester?
When choosing where to stay in Chester, Vermont, you’ll find a variety of charming neighborhoods that offer unique experiences. Situated in the scenic heart of Vermont, Chester provides a peaceful setting with easy access to lush countryside and local amenities. Whether you prefer staying close to historic downtown areas or nestled near tranquil natural landscapes, each neighborhood offers its own distinct character. Booking a vacation rental in Chester allows you to enjoy authentic Vermont hospitality while exploring this picturesque region at your own pace. Discover the perfect home base that suits your travel style and makes your visit memorable.
Chester Depot
Located in a charming part of the region, Chester Depot offers convenient access to local attractions and scenic surroundings. Here, you can enjoy a peaceful stay with easy connections to explore the area's natural beauty.
View 45+ Rentals in Chester DepotBest Times to Visit Chester
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you experience the region’s unique seasonal charm, whether you're seeking quiet winter retreats or vibrant summer escapes in Chester, Vermont.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and lush landscapes in this picturesque destination, making it ideal for outdoor activities and scenic drives.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn brings vibrant foliage that transforms the region into a breathtaking sight, perfect for exploring local trails and enjoying the crisp air.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
The winter season offers a tranquil atmosphere with opportunities for cozy getaways and scenic snowy views in the area.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
Spring (March to May)
In spring, the landscape begins to bloom, providing a quieter experience before the busy summer season starts, ideal for peaceful retreats.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Chester
How to Book Your Chester Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chester
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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
- Enjoy outdoor seating areas perfect for relaxing and soaking up the scenic views of the surrounding countryside.
- Take advantage of spacious decks or patios to dine al fresco amid the fresh mountain air.
- Explore well-maintained walking trails or pathways that wind through the natural landscape.
- Make use of private yards or gardens, ideal for outdoor games and family gatherings.
- Utilize outdoor fire pits for cozy evenings and making memories under the stars.
- Benefit from ample parking spaces, convenient for exploring the region’s outdoor attractions.
- Access outdoor recreational amenities such as swimming pools or hot tubs, if available on the property.
Top Attractions Around Chester
What attractions are nearby?
Enjoy a variety of outdoor activities and charming local attractions just moments from your vacation rental here in Chester, Vermont, offering you the perfect opportunity to explore the scenic region and immerse yourself in its natural beauty and small-town charm.
Family Activities
- Chester Village Stroll: Discover charming local shops, cafes, and historic sites that capture the essence of this quaint Vermont town.
- Hiking in the Green Mountain National Forest: Enjoy family-friendly trails with scenic views just minutes from your rental, perfect for exploring Vermont's natural beauty.
- Visit to the Orvis Fly Fishing School: Introduce the family to the art of fly fishing at this renowned school nestled near here, offering great outdoor recreation options.
- Exploring Chester Dam and the Mill River: Relax by the tranquil waters and enjoy picnicking or gentle walks along the waterway that flows through this region.
Adult Activities
- Exploring local art galleries: Immerse yourself in the vibrant arts scene that showcases the region's creative talents and fosters a unique cultural experience.
- Enjoying scenic hikes and nature walks: Take advantage of the area's picturesque trails to connect with the natural beauty and tranquility that surrounds your vacation rental.
- Visiting historic sites: Discover the rich history woven into the fabric of this destination through well-preserved landmarks and museums.
- Savoring farm-to-table dining experiences: Indulge in the region’s fresh, locally sourced cuisine at acclaimed eateries close to your rental home.
Other Places to Stay in Chester, VT
DaVallia Art & Accents
Bonnie's Bundles Dolls
Chester Depot
Chester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Flavors: Take the time to enjoy the region's renowned culinary scene by visiting local eateries and farmers' markets, enhancing your authentic Chester experience.
- Plan Outdoor Adventures: Make the most of the area's natural beauty with outdoor activities like hiking or scenic drives, ensuring a memorable stay in this charming destination.
- Discover Unique Shops: Wander through quaint boutiques and local craft stores to find one-of-a-kind souvenirs that capture the spirit of this picturesque region.
- Check for Seasonal Events: Stay updated on seasonal festivals and events happening during your visit, adding a special touch to your trip here.
Transportation Options
- Chester Transportation Services: Reliable shuttle and taxi options are available to help you explore the region conveniently from your vacation rental.
- Rental Car Agencies: Several car rental services operate nearby, giving you the freedom to discover this scenic area at your own pace.
- Public Transit: Local buses provide an affordable way to travel around the city and access key points of interest in the region.
- Bike Rentals: For a scenic and eco-friendly experience, bike rentals are widely accessible for exploring here’s charming surroundings.
Local Customs Options
- Chester's Historic Main Street: You will notice that the local community takes pride in preserving its historic charm through well-maintained buildings and storefronts along the main street.
- Seasonal Maple Syrup Tapping: Engaging with the region’s agricultural roots, residents often participate in traditional maple syrup tapping during early spring, which is celebrated locally.
- Community Craft Fairs: Visitors can experience the region's appreciation for handmade crafts at seasonal fairs that highlight local artisans and their work.
- Winter Festivities and Snow Sports: Embracing the winter season, locals partake in and observe community-led snow sports and festive events that reflect the area's seasonal traditions.
Chester Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals 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 Vacation Rentals in Chester:
- Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
- Vermont Charm in the 1840 Gideon Lee House
- Log Cabin Retreat - Chester, VT 25 Acres + State Forest Access
- Cheerful residential home with lots of space
- Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort
- Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
- Riverfront, family fun, amazing rec room, close to Magic & Okemo
- Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
- Amazing Custom Home on 40+ Acres
- Spacious 5-bedroom chalet with AC and WiFi in charming Chester
2. Which vacation homes in Chester are best for families?
If you are looking for a family-friendly vacation home in Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester:
3. How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 93 in the Chester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chester.
4. What is the cancellation policy for vacation rentals in Chester, Vermont?
Cancellation policies vary by listing, so you should review the specific property's policy on its page or contact the owner directly to understand the terms and any potential fees.
5. Are there any additional fees I should be aware of when booking a vacation rental in this region?
Additional fees such as cleaning fees, service charges, or taxes are often listed during the booking process. Be sure to read the full details of each listing for clarity before confirming your reservation.
6. How do I verify the safety and cleanliness standards of vacation rentals here?
You can check the reviews left by previous guests and the amenities listed on the property page. For further assurance, contact the owner directly with any safety or cleanliness questions prior to booking.
7. Can I get a detailed description of the amenities included in my chosen rental?
Yes, each property listing provides a comprehensive list of amenities. If you need more specific information, reaching out to the property owner is recommended before finalizing your reservation.
8. What is the process for modifying or canceling my booking in this area?
The process for changes depends on the individual listing's policies. You should review the cancellation and modification options on the property page or contact the owner for assistance.
Chester Top Rated Vacation Rentals
House
9.8(16 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $340/Night
7 Nights - US $2,378
House
9.4(39 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $209/Night
7 Nights - US $1,462
Other
9.2(11 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $523/Night
7 Nights - US $3,662
Other
8.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $189/Night
7 Nights - US $1,323
