Night Travels - Vacation Rentals in Chester

Beautiful Modern Loft In Wine Country! From US $180
         

10.0 (271 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Downtown Loft Amazing Bath Tub & Shower #9 From US $174
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The Conner House B&B From US $157
         

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10.0 (19 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Downtown historic main street From US $129
         

9.6 (181 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Chester

Over 105+ Luxury Places to Stay in or Near Chester
Missouri Castle w/Private Lake, Pool & 100 Acres! From US $1,550
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Microtel Inn & Suites by Wyndham Sainte Genevieve From US $907
         

8.6 (76 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Gorgeous, downtown house! From US $875
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
TreeLoft at BaseCamp From US $614
         

10.0 (5 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Super 8 by Wyndham Perryville From US $602
         

8.0 (327 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Mediterranean House - Beautiful Downtown House From US $512
         

New! Luxury Meets Nature - TreeRise at BaseCamp From US $439
         

10.0 (1 Review)
Cabin
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Top-Rated Vacation Rentals with a Pool in Chester

Over 14+ Top-Rated Vacation Rentals with a Pool in or Near Chester
Holiday Inn Express & Suites Perryville by IHG From US $100
         

9.2 (534 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Hotel & Suites Sparta by IHG From US $92
         

9.2 (367 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Super 8 by Wyndham Perryville From US $76
         

8.4 (935 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Baymont by Wyndham Chester IL From US $75
         

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7.7 (124 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Pool
Briarwood Inn of Sparta From US $72
         

7.4 (122 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Days Inn by Wyndham Perryville From US $77
         

6.8 (415 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Quality Inn Perryville I-55 From US $86
         

6.6 (124 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chester

Over 23+ Pet-Friendly Vacation Rentals in or Near Chester
Elegant 3BR in the Heart of Historic Ste Genevieve From US $274
         

Downtown Urban Loft above Restaurants #1 From US $175
         

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9.7 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Urban Lofts From US $238
         

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9.2 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown Loft w/Amazing Bath Tub & Shower From US $222
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Haven Little Hidden Gem Sleeps 4 From US $157
         

9.8 (53 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hot Tub & Creek Views: Secluded Perryville Cabin From US $170
         

9.8 (8 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Chester on PetFriendly.io

Large Vacation Homes & Villas in Chester

Over 3+ Large Vacation Homes & Villas in or Near Chester
Ste Genevieve Home on 17 Acres, Near Wineries! From US $596
         

9.8 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Twin Turret Farm and Castle From US $1,000
         

4.9 (15 Reviews)
Other
  • Air Conditioner
  • Pool
  • TV

Wheelchair Accessible Vacation Homes in Chester

Over 3+ Wheelchair Accessible Vacation Homes in or Near Chester
Days Inn by Wyndham Perryville MO From US $80
         

6.0 (68 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Microtel Inn & Suites by Wyndham Sainte Genevieve From US $76
         

Baymont by Wyndham Chester IL From US $80
         

8.6 (350 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Chester Varoom and Airbnb Places to Stay Under $200

Over 56+ Chester Varoom and Airbnb Places to Stay Under $200
Lodge at the Longbranch next to the Longbranch Saloon From US $199
         

10.0 (55 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Brewer Guesthouse Tiny Home with Patio and Yard! From US $99
         

10.0 (6 Reviews)
House
  • Parking
  • Accessibility
  • Security/Safety
K-River Motel & Campground From US $67
         

8.8 (20 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Cottage w/Yard, Walk to Historic Attractions From US $191
         

10.0 (41 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
'The Brewer Guesthouse' Tiny Home w/Patio & Yard! From US $128
         

Entire Private Home in Perryville, MO From US $92
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cozy 1.5 story bungalow in downtown Ste. Genevieve! From US $96
         

Instantly Bookable Vacation Homes in Chester

Over 17+ Instantly Bookable Vacation Homes in or Near Chester
Doves Nest Guest House Tranquil & Relaxing From US $255
         

Charming modern farmhouse - four miles from WSRC
New
From US $237
         

New
Other
  • Air Conditioner
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  • Balcony/Terrace

About Chester Vacation Rentals

With more than 114 Chester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Nighttravels 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 Nighttravels 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 734.91 ft² on average, with prices averaging $245 a night.

Nighttravels 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
Vacation Homes 38
Holiday Apartments 31
Hotels with Suites 31
Cabin Rentals 5
Cottages 4
Others 3
B&B 1

Use these Quick Filters to Find a Vacation Rental in Chester

Pro Tip: Nighttravels makes it easy to compare the best listings on Nighttravels homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Nighttravels 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