Owner Direct Vacation Rentals in Chesterfield

The Best Owner Direct Vacation Rentals in Chesterfield. Explore thousands of vacation home rentals, large cabins, and villas near Chesterfield

50ft Stationary House Boat From US $200
         

10.0 (1 Review)
Boat Rental
  • Air Conditioner
  • Parking
  • Balcony/Terrace
The Cottages at Northpointe on Anchor Bay From US $315
         

10.0 (13 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
TownePlace Suites by Marriott Chesterfield From US $121
         

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9.4 (157 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Peaceful Studio Flat near Downtown Mount Clemens From US $158
         

9.5 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Cozy Canal Tiny Home | Sleeps 4 | Boat Parking From US $144
         

10.0 (15 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Waterfront Home in Chesterfield with Views! From US $506
         

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9.0 (2 Reviews)
House
  • Parking
  • Accessibility
  • Security/Safety
`Charlie`s by the Bay` # 4 From US $235
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
2 Bed, 1 Bath, Upper Level Unit From US $198
         

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9.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Luxury Places to Stay in Chesterfield

Over 73+ Luxury Places to Stay in or Near Chesterfield
Stunning Luxury Colonial Estate From US $978
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Easy Stay in Anchor Bay - Gym | Theater | Sleeps12 From US $589
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
4 Bed, 2 Bath, Upper Flat From US $550
         

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New
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
3 Bed, 1 Bath, Upper Flat From US $383
         

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New
Apartment
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  • Parking
  • Security/Safety
Charlies by the Bay Unit 1 From US $376
         

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New
Apartment
  • Air Conditioner
  • Pet Friendly
  • View
Charlie`s by the Bay #3 From US $343
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
3 Bed, 2 Bath House on Canal with Boat Well Included From US $341
         

Top-Rated Vacation Rentals with a Pool in Chesterfield

Over 8+ Top-Rated Vacation Rentals with a Pool in or Near Chesterfield
TownePlace Suites by Marriott Chesterfield From US $154
         

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9.4 (41 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • View
Fairfield Inn & Suites by Marriott Detroit Chesterfield From US $112
         

Hampton Inn & Suites Detroit/Chesterfield Township From US $96
         

8.4 (1008 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn & Suites Detroit/Chesterfield From US $110
         

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8.4 (166 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn & Suites by Marriott Detroit Chesterfield From US $108
         

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8.3 (77 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Private Pool
Holiday Inn Express & Suites Chesterfield by IHG From US $91
         

8.0 (547 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
You wanna take a trip for peace From US $225
         

New
House
  • Air Conditioner
  • Pool
  • Security/Safety

Pet-Friendly Vacation Rentals in Chesterfield

Over 11+ Pet-Friendly Vacation Rentals in or Near Chesterfield
Near Detroit Metro Area New Baltimore Home! From US $272
         

`Charlie`s by the Bay` Unit 1 From US $206
         

9.8 (20 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Anchor Bay Boathouse From US $235
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Near Detroit Metro Area: New Baltimore Home! From US $167
         

Pet Friendly/Gated Backyard/Game room/Hot Tub From US $267
         

Private Yard w/Patio: Family Getaway in Macomb From US $254
         

Large Vacation Homes & Villas in Chesterfield

Over 7+ Large Vacation Homes & Villas in or Near Chesterfield
6-Bedrooms, 1.5-Bath Ranch Style Unit From US $324
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
50ft Stationary House Boat with Upper Sun Deck From US $108
         

8.4 (5 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Elegant Oasis: 4-Bedroom Home Away from Home From US $462
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV

Wheelchair Accessible Vacation Homes in Chesterfield

Over 2+ Wheelchair Accessible Vacation Homes in or Near Chesterfield
Tru By Hilton Chesterfield Township Detroit From US $104
         

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8.5 (295 Reviews)
Hotel
  • Parking
  • Wheelchair Accessible
  • Accessibility
Tru by Hilton Chesterfield Township Detroit From US $83
         

8.6 (346 Reviews)
Hotel
  • Parking
  • Wheelchair Accessible
  • Accessibility

Chesterfield Varoom and Airbnb Places to Stay Under $200

Over 29+ Chesterfield Varoom and Airbnb Places to Stay Under $200
60ft Stationary House Boat From US $175
         

New
Boat Rental
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Small Studio House on the Water on Private Street From US $200
         

LodgeKeeper From US $108
         

7.2 (13 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
New! Luxury 1BR Flat near Downtown Mount Clemens From US $129
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Chesterfield

Over 18+ Instantly Bookable Vacation Homes in or Near Chesterfield
Very cozy 1 room dwelling w/twin bed From US $58
         

9.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cozy 2-bedroom condo with WiFi, AC in peaceful New Baltimore From US $150
         

6.8 (3 Reviews)
Condo
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Modern, Rustic[3BR/1.5BA]Townhome in Mt. Clemens From US $209
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Charming Lakefront Vacation Rental From US $239
         

9.4 (64 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Canal Home From US $260
         

9.2 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Chesterfield Vacation Rentals

With more than 82 Chesterfield vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect 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 Ownerdirect 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 628.98 ft² on average, with prices averaging $220 a night.

Ownerdirect 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
Vacation Homes 34
Holiday Apartments 28
Hotels with Suites 11
B&B 1
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Chesterfield

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

Complexes around Chesterfield, MI