Coffee Hawaii - Vacation Rentals in Chesterfield

Modern 1 bedroom 1 bath apartment From US $96
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Furnished 2ND FLOOR 2-bedroom Downtown Anderson IN From US $90
         

9.3 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Best Western Plus Anderson From US $114
         

8.8 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Lux 1 bed/1 bath unit ideal for traveling professional From US $74
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Spacious Modern 1bd/1bth Mins Downtown Anderson From US $85
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
The Winner’s Circle - Pool, Hot Tub, Next to Harrah’s Casino From US $292
         

Charming Family-Friendly Retreat From US $343
         

8.8 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Bright, furnished studio-Perfect for traveling professionals or students From US $104
         

8.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Luxury Places to Stay in Chesterfield

Over 38+ Luxury Places to Stay in or Near Chesterfield
Charming 3BR Home in Historic Downtown Anderson From US $238
         

Tru By Hilton Anderson From US $187
         

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8.5 (203 Reviews)
Hotel
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  • Parking
  • Pool
Modern 2BR Upstairs Unit - Sleeps 4 Free Parking From US $137
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Fairfield Inn & Suites by Marriott Anderson From US $136
         

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8.5 (92 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn & Suites by Marriott Anderson From US $128
         

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8.8 (523 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Chesterfield

Over 7+ Top-Rated Vacation Rentals with a Pool in or Near Chesterfield
Tru By Hilton Anderson From US $109
         

8.8 (275 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Plus Anderson From US $102
         

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8.7 (289 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Quality Inn & Suites Anderson I-69 From US $80
         

8.4 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Hotel & Suites Anderson by IHG From US $123
         

8.4 (190 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Hotel & Suites ANDERSON NORTH by IHG From US $108
         

Quality Inn & Suites Anderson I-69 From US $75
         

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7.9 (331 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn Anderson South From US $104
         

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7.7 (313 Reviews)
Hotel
  • Parking
  • Pool
  • Wheelchair Accessible

Pet-Friendly Vacation Rentals in Chesterfield

Over 6+ Pet-Friendly Vacation Rentals in or Near Chesterfield
Days Inn by Wyndham Anderson IN From US $51
         

5.2 (283 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Red Roof Inn Anderson, IN From US $69
         

6.0 (495 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Duplex Near Anderson University From US $86
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Motel 6-Anderson, IN From US $59
         

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7.1 (405 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Anderson Bungalow Near University + Downtown! From US $147
         

9.4 (3 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Anderson Inn, Anderson, Indiana From US $76
         

6.0 (102 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Chesterfield

Over 1+ Large Vacation Homes & Villas in or Near Chesterfield
The Cozy Cottage - plenty of privacy & work space From US $314
         

9.8 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Chesterfield

Over 1+ Wheelchair Accessible Vacation Homes in or Near Chesterfield
Red Roof Inn Anderson, IN From US $66
         

5.7 (109 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Chesterfield Vacation Rentals and Airbnb Places to Stay Under $200

Over 10+ Chesterfield Vacation Rentals and Airbnb Places to Stay Under $200
Anderson Chesterfield Travel Inn From US $78
         

7.8 (271 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Security/Safety
Anderson Inn From US $85
         

5.6 (308 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Relaxing 3beds/2 baths From US $68
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Wellness Facilities
Charming Farmhouse < 1/2 Mile to AU Campus! From US $174
         

New
House
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly

Instantly Bookable Vacation Homes in Chesterfield

Over 1+ Instantly Bookable Vacation Homes in or Near Chesterfield
7 Mi to Mounds State Park: Indiana Home w/Porch! From US $216
         

9.6 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Chesterfield Vacation Rentals

With more than 47 Chesterfield vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Coffeeshawaii 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 Chesterfield.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Coffeeshawaii Chesterfield, 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 Chesterfield. Places to stay near Chesterfield are 164.42 ft² on average, with prices averaging US $140 a night.

Coffeeshawaii makes it easy and safe to find and compare vacation rentals in Chesterfield 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 Chesterfield

Type Count
Hotels 19
Vacation Homes 16
Holiday Apartments 11
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Chesterfield

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

Weather in Chesterfield

View the weather forecast for Chesterfield before booking your Chesterfield 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

Chesterfield Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chesterfield?
How many vacation rentals are available in Chesterfield?

Currently, the total number of properties listed in 2026 is over 47 in the Chesterfield area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesterfield.