Best Vacation Homes in Chester
Other
9.6(5 Reviews)
4 Bedrooms
3 Baths
9 Guests
3800 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $320/Night
7 Nights - US $2,241
Bed & Breakfast
10.0(6 Reviews)
1 Bedroom
1 Bath
5 Guests
796.53 ft²
- Fireplace/Heating
- Balcony/Terrace
View
Breakfast
US $195/Night
7 Nights - US $1,365
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $261/Night
7 Nights - US $1,827
House
10.0(69 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $122/Night
7 Nights - US $854
House
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
1001.04 ft²
Spa- Fireplace/Heating
- Parking
Internet
US $219/Night
7 Nights - US $1,535
House
10.0(45 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $128/Night
7 Nights - US $897
House
10.0(24 Reviews)
3 Bedrooms
1 Bath
6 Guests
1600 ft²
- Fireplace/Heating
Pool- Balcony/Terrace
- Breakfast
US $211/Night
7 Nights - US $1,474
House
10.0(13 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $346/Night
7 Nights - US $2,419
Chester Luxury Rentals
Hotel
4 Baths
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $617/Night
7 Nights - US $4,316
Hotel
4 Baths
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $617/Night
7 Nights - US $4,316
Apartment
6.0(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
Hot Tub- Fireplace/Heating
- Kitchen
Air Conditioner
US $577/Night
7 Nights - US $4,037
Hotel
3 Baths
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $462/Night
7 Nights - US $3,235
Hotel
3 Baths
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $462/Night
7 Nights - US $3,235
House
10.0(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $459/Night
7 Nights - US $3,213
House
9.8(28 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $346/Night
7 Nights - US $2,419
House
9.8(6 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $322/Night
7 Nights - US $2,255
Chester Pet Friendly Vacation Rentals
House
9.8(35 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $297/Night
7 Nights - US $2,079
House
9.5(2 Reviews)
3 Bedrooms
1 Bath
6 Guests
1496.18 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $140/Night
7 Nights - US $980
House
10.0(13 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $514/Night
7 Nights - US $3,595
Apartment
9.8(16 Reviews)
4 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $193/Night
7 Nights - US $1,353
Apartment
9.0(5 Reviews)
4 Bedrooms
1 Bath
10 Guests
1603.82 ft²
- Fireplace/Heating
- Breakfast
- Pet Friendly
- Parking
US $215/Night
7 Nights - US $1,502
House
9.8(9 Reviews)
1 Bedroom
1 Bath
5 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $232/Night
7 Nights - US $1,625
House
9.6(7 Reviews)
4 Bedrooms
2 Baths
8 Guests
2500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $250/Night
7 Nights - US $1,747
House
4 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $385/Night
7 Nights - US $2,695
Chester Large Vacation Homes
House
10.0(1 Review)
1 Bedroom
1 Bath
10 Guests
Child Friendly
US $132/Night
7 Nights - US $924
Apartment
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $255/Night
7 Nights - US $1,784
House
10.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $378/Night
7 Nights - US $2,646
House
4 Bedrooms
4 Baths
16 Guests
720 ft²
- Child Friendly
US $370/Night
7 Nights - US $2,590
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.
Best Times to Visit Chester
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as the region offers distinct seasonal appeal that suits various interests and activities throughout the year.
Peak Season Highlights
Summer (June to August)
This is the most popular time to visit, as the warm weather and longer days make outdoor activities more enjoyable in this scenic destination.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 50°F to 60°F
Fall (September to October)
During these months, the region experiences mild weather and stunning fall foliage, providing a picturesque setting for your vacation.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
The winter months see fewer visitors, offering a quiet retreat with cold temperatures ideal for cozy getaways and enjoying the winter landscape.
Average Temperature Daytime: 20°F to 30°F - Nighttime: 10°F to 20°F
Spring (March to May)
Early spring brings cooler weather and less crowded conditions, making it a peaceful time to explore the area's natural beauty.
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 grilling on a private patio or barbecue area to make the most of meals in the fresh air.
- Take advantage of spacious yards or gardens perfect for outdoor activities and relaxation amid scenic surroundings.
- Experience direct access to hiking trails or nature walks right from your doorstep in this picturesque region.
- Relax by a fire pit during cool evenings, ideal for storytelling and enjoying the tranquil outdoor environment.
- Make use of available outdoor seating areas designed for social gatherings or quiet moments amidst nature.
- Benefit from nearby fishing spots or access to lakes and streams within the area’s outdoor landscape.
- Utilize outdoor recreational facilities such as sports courts, playgrounds, or designated areas for outdoor sports when available.
Top Attractions Around Chester
What attractions are nearby?
Nearby in this charming region, you can enjoy a variety of outdoor activities such as fishing, hiking, and exploring scenic nature trails, making it an ideal destination for those seeking to immerse themselves in the natural beauty of Chester, Montana.
Family Activities
- Chester Motor Museum: Discover local history and vintage vehicles that offer an engaging experience for families seeking a cultural outing in the area.
- Placid Lake State Park: Enjoy scenic picnics, fishing, and swimming amidst stunning natural surroundings at this popular outdoor destination nearby.
- Bear Gulch Trail: Embark on family-friendly hikes through beautiful landscapes, perfect for exploring here with young adventurers.
- Fishing on the North Fork of the Flathead River: Relax and bond while trying your luck at fishing in the peaceful waters just outside of town.
Adult Activities
- Hiking and Nature Walks: Explore scenic trails around the region, offering tranquil views and an opportunity to immerse yourself in Montana's natural beauty.
- Wildlife Viewing: Discover diverse wildlife habitats nearby, perfect for observing native animals in their natural environment.
- Fishing on Local Rivers: Enjoy peaceful moments by fishing in the area’s pristine rivers, known for abundant trout and other freshwater species.
- Historical Exploration: Visit local museums and historical sites that highlight Chester’s rich heritage and the area's cultural significance.
Chester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Shops: Take time to enjoy the unique eateries and boutiques that reflect the charm of this area, enhancing your overall experience.
- Plan Outdoor Activities: Make the most of the region’s scenic beauty by engaging in outdoor pursuits such as fishing, hiking, or wildlife viewing right from your vacation rental.
- Visit Nearby Natural Attractions: Discover the area's natural landscapes and serene settings that offer perfect spots for relaxation and photography during your stay.
- Book in Advance: Secure your preferred vacation rental early to ensure availability and get the best options tailored to your travel plans in this destination.
Transportation Options
- Chester Airport: A convenient nearby regional airport that offers limited commercial flights, making it suitable for travelers arriving from major hubs who prefer quick access to the area.
- Private Car Services and Taxis: Readily available in the region, these services provide flexible transportation options for exploring Chester and the surrounding natural scenery at your own pace.
- Rental Cars: Local agencies offer a variety of vehicles, allowing you to explore the area's scenic landscapes comfortably and on your schedule.
- Public Transit: Limited but useful bus services connect Chester with neighboring towns, serving travelers seeking budget-friendly transportation within this part of Montana.
Local Customs Options
- Local Art and Craftsmanship: Embrace the region’s rich heritage by exploring local art galleries and craft markets that showcase Chester’s unique Western Montana culture.
- Traditional Western Hospitality: Experience the warm welcome and friendly interactions typical of this destination, reflecting its strong ties to Western customs.
- Community Events and Gatherings: Participate in seasonal festivals and community gatherings that highlight the area’s dedication to celebrating local traditions.
- Respect for Nature and Conservation: Observe the region’s emphasis on outdoor stewardship through responsible outdoor activities and preservation efforts during your stay.
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:
- The House on 219
- Little Blue Cabin
- The Homestead - 3 bedroom House in the Heart of Chester
- Mountain Lakeview Lodge
- Great Northern Bed & Breakfast
- Entire home in Valier, Montana
- Patio, Grill & Outdoor Dining: Conrad Home!
- Glacier Getaway- Family Friendly, 3 Bedroom Duplex
- Cowboy Condo in Charming Shelby
- Suite Country Downtown #2 Cozy and Relaxing just minutes from Lake Frances
2. How many vacation rentals have private pools in Chester?
There are 3 vacation rentals with private pools near Chester. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 97 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.
5. What is the cancellation policy for vacation rentals in Chester, Montana?
Cancellation policies vary depending on the listing. You should review the specific property's policy on its page or contact the host directly to understand the terms related to cancellations and refunds.
6. How do I secure my booking at a vacation rental in this region?
To reserve a vacation rental here, you typically need to complete the booking process through the listing platform, which may include providing payment details and confirming your reservation. Always verify the booking requirements on the individual property page.
7. Are there any specific check-in or check-out times I should be aware of in Chester's vacation rentals?
Check-in and check-out times are set by each property owner. Details regarding arrival and departure hours are usually listed on the property page or communicated directly by the host upon confirmation of your booking.
8. What amenities are generally available in vacation rentals in this area?
Most rentals offer amenities typical of the region, such as fully equipped kitchens, Wi-Fi, and outdoor spaces. To ensure the property meets your needs, review the amenities list on the listing carefully or contact the host for specific questions.
9. Is there any local guidance available for guests staying in Chester, Montana's vacation rentals?
While many hosts provide local tips and recommendations, it's beneficial to read the property description thoroughly and reach out to the host for personalized suggestions about exploring the area during your stay.
Chester Top Rated Vacation Rentals
Hotel
9.4(1001 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
US $130/Night
7 Nights - US $907
US $165/Night
7 Nights - US $1,157
US $152/Night
7 Nights - US $1,067
Hotel
9.0(1002 Reviews)
1 Bath
- Spa
- Pool
- Balcony/Terrace
- Breakfast
US $116/Night
7 Nights - US $811
Hotel
8.9(240 Reviews)
1 Bath
381.22 ft²
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $127/Night
7 Nights - US $889
Hotel
8.9(112 Reviews)
9 Baths
638.66 ft²
- Private Pool
Oceanfront- Hot Tub
- Spa
US $165/Night
7 Nights - US $1,153
Hotel
8.9(60 Reviews)
1 Bath
385.35 ft²
- Private Pool
- Hot Tub
Skiing- Fireplace/Heating
US $186/Night
7 Nights - US $1,303
US $156/Night
7 Nights - US $1,093
