Maimon Beach - Vacation Rentals in Chester

The Homestead - 3 bedroom House in the Heart of Chester From US $238
         

10.0 (24 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Great Northern Bed & Breakfast From US $195
         

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9.5 (16 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Mountain Lakeview Lodge From US $514
         

10.0 (13 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Great northern bed and breakfast From US $232
         

9.8 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The House on 219 From US $133
         

10.0 (69 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Little Blue Cabin From US $161
         

10.0 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Entire home in Valier, Montana From US $698
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Patio, Grill & Outdoor Dining: Conrad Home! From US $183
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Chester

Over 88+ Luxury Places to Stay in or Near Chester
Suite Country Downtown : Enjoy Two Suites #1 & #2: Cozy and relaxing From US $577
         

FOOTHILLS LOOKOUT INN -Come home to Montana! From US $463
         

9.8 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Chester

Over 28+ Top-Rated Vacation Rentals with a Pool in or Near Chester
Best Western Shelby Inn & Suites From US $130
         

9.4 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Plus Havre Inn & Suites From US $156
         

9.4 (537 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
AmericInn by Wyndham Havre From US $156
         

9.2 (657 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Plus Havre Inn & Suites From US $186
         

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9.1 (57 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn & Suites Gateway to Glacier National Park From US $116
         

9.0 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
AmericInn by Wyndham Havre From US $165
         

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8.9 (112 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Plus Great Northern Inn From US $138
         

8.8 (692 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Shelby Inn & Suites From US $127
         

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8.8 (233 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Chester

Over 19+ Pet-Friendly Vacation Rentals in or Near Chester
The Westland Suite - Historic Lodging, Contemporary Comforts From US $238
         

9.8 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The Homestead From US $140
         

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9.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish Mid Century 4-Bedroom House in Fort Benton From US $239
         

9.6 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
ENTIRE LOWER LEVEL - Mountain Lakeview Lodge From US $502
         

Freshly remodeled vintage 2 bedroom From US $143
         

9.4 (38 Reviews)
House
  • Pet Friendly
  • Security/Safety
  • Child Friendly
Valier Lodge near Lake Francis From US $353
         

4.0 (1 Review)
House
  • Pet Friendly
  • Bedding/Linens
  • Kitchen
See More Pet-Friendly Vacation Rentals in Chester on PetFriendly.io

Large Vacation Homes & Villas in Chester

Over 4+ Large Vacation Homes & Villas in or Near Chester
The Westland Suite From US $215
         

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9.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Chester

Over 3+ Wheelchair Accessible Vacation Homes in or Near Chester
Super 8 by Wyndham Conrad From US $103
         

8.5 (200 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Grand Union Hotel From US $172
         

9.4 (321 Reviews)
Hotel
  • Parking
  • Designated Smoking Area
  • TV
Super 8 by Wyndham Havre From US $101
         

6.6 (196 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Chester Vacation Rentals and Airbnb Places to Stay Under $200

Over 28+ Chester Vacation Rentals and Airbnb Places to Stay Under $200
Comfort Inn & Suites Gateway to Glacier National Park From US $136
         

8.2 (202 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Super 8 by Wyndham Conrad From US $90
         

8.8 (726 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Chester

Over 34+ Instantly Bookable Vacation Homes in or Near Chester
Cowboy Condo in Charming Shelby From US $303
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • TV
Tranquil 4-bedroom Glacier View Getaway Montana From US $320
         

Life in A Small Town From US $192
         

9.8 (11 Reviews)
House
  • Parking
  • Designated Smoking Area
  • TV
A Night in a Homestead From US $225
         

8.0 (1 Review)
House
  • Parking
  • Balcony/Terrace
  • Security/Safety

About Chester Vacation Rentals

With more than 97 Chester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Maimonbeach and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chester.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Maimonbeach Chester, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chester. Places to stay near Chester are 315.61 ft² on average, with prices averaging $247 a night.

Maimonbeach makes it easy and safe to find and compare vacation rentals in Chester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Chester

Type Count
Hotels with Suites 54
Vacation Homes 34
Holiday Apartments 4
B&B 2
Cottages 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Chester

Pro Tip: Maimonbeach makes it easy to compare the best listings on Maimonbeach homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Maimonbeach homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chester.

Weather in Chester

View the weather forecast for Chester before booking your Chester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Chester Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chester?
How many vacation rentals have private pools in Chester?

There are 1 vacation rentals with private pools near Chester. Top-rated homes that have access to a swimming pool include:

How many vacation rentals are available in Chester?

Currently, the total number of properties listed in 2026 is over 97 in the Chester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chester.