Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Affordable Suites of America Detroit-Warren

3.0 star property
7.4 out of 10, Good, (1348)
"Very nice suite. Room was clean and comfortable. In the room I was assigned, I would suggest changing out the tattered desk chair and the heavily soiled chair in LR area. Otherwise, the room was great."
The price is AU$123
includes taxes & fees
7 Sept - 8 Sept
Affordable Suites of America Detroit-Warren

Full home, 420 friendly

9.0 out of 10, Wonderful, (11)
"This was a great place to record my music video. The house was really nice and it had a lot of things. "
The price is AU$489
includes taxes & fees
7 Sept - 8 Sept
Full home, 420 friendly

Home in Royal Oak w/ pool & sauna & dream garage

9.2 out of 10, Wonderful, (20)
"Everything about this stay was seamless and easy. Thank you so much!"
Home in Royal Oak w/ pool & sauna & dream garage

Blueberry Hill...sweet 3 bedroom vacation home in beautiful St. Clair.

10.0 out of 10, Exceptional, (24)
"Our second time staying for an annual family function in the area and just as happy with it as the first time. Betty is a great host and the place has everything we could ask for. "
Blueberry Hill...sweet 3 bedroom vacation home in beautiful St. Clair.

Graber's Lake Getaway- Clean and Beautiful! Great Work from home location!

10.0 out of 10, Exceptional, (58)
"Loved waking up looking at the water. Comfortable beds and had everything we needed. Great views and great location to the boat launch. "
Graber's Lake Getaway- Clean and Beautiful! Great Work from home location!

private and spacious

10.0 out of 10, Exceptional, (74)
"Very nice place and quiet.Will book again if I’m on the area."
The price is AU$201
includes taxes & fees
7 Sept - 8 Sept
private and spacious

Charming 2-bedroom cottage with WiFi, AC on a peaceful Harsens Island canal.

9.6 out of 10, Exceptional, (8)
"This property is amazing, so well kept, and super clean. Justin was a great host and always available for a question. The beds were so comfy, I slept like a baby! We will definitely be back to rent this beauty again. Thanks for everything Justin! "
Charming 2-bedroom cottage with WiFi, AC on a peaceful Harsens Island canal.

SelfieBnb | Great for Content Creation & Selfies

10.0 out of 10, Exceptional, (12)
"Super great place"
The price is AU$489
includes taxes & fees
29 Sept - 30 Sept
SelfieBnb | Great for Content Creation & Selfies

420 friendly sleeps 8 in Detroit’s east side with WiFi, AC. Enjoy your stay

8.0 out of 10, Very good, (7)
"I stayed here for 2 nights and I seen bugs, dishwasher was leaking onto the floor and we were only provided with 1 trash bag through the whole stay. I told the lady about bugs and the leaking but never got a text back. I asked about internet password and she instantly texted me back. "
420 friendly sleeps 8 in Detroit’s east side with WiFi, AC. Enjoy your stay

Charming cottage right on the canals of Lake St. Clair!

10.0 out of 10, Exceptional, (11)
"This house was perfect for our stay and location close to our favorite fishing spot, after long day on lake got to the house had dinner and caught more fish off back yard and watched amazing sunset. "
Charming cottage right on the canals of Lake St. Clair!

NEW! 4BR | Indoor Pool on the Bay in Boat Town USA

3.0 star property
9.4 out of 10, Exceptional, (3)
"Beautiful property, well maintained, awesome and fun amenities. We felt like we were at home."
NEW! 4BR | Indoor Pool on the Bay in Boat Town USA

Evanston BnB

3.0 star property
8.4 out of 10, Very good, (11)
"We enjoyed our staycation it was very chill and had extra blankets covers and pillows "
The price is AU$252
includes taxes & fees
7 Sept - 8 Sept
Evanston BnB

80ft Seawall~6beds~Direct Lake Access~Family Friendly~Excellent for Fishing

80ft Seawall~6beds~Direct Lake Access~Family Friendly~Excellent for Fishing

Large 5 Bedroom Home King Bed

9.0 out of 10, Wonderful, (18)
"The property was nice,overall great stay"
The price is AU$715
includes taxes & fees
12 Sept - 13 Sept
Large 5 Bedroom Home King Bed

Entire home in Grosse Pointe Park ... Welcome to the MotorcityBnB!

10.0 out of 10, Exceptional, (23)
"Great place and super well maintained!! "
Entire home in Grosse Pointe Park ... Welcome to the MotorcityBnB!

The Harbor House - Entire 1st Floor Waterfront

10.0 out of 10, Exceptional, (27)
"Great place to stay-very clean! Beautiful spot close to restaurants and the river is in the backyard…"
The price is AU$422
includes taxes & fees
15 Sept - 16 Sept
The Harbor House - Entire 1st Floor Waterfront

St.Clair Canal Home w/ Pontoon Boat/Jet Ski's - Perfect for Families/Fishermen

9.6 out of 10, Exceptional, (78)
"The hosts were very nice and we enjoyed our stay"
St.Clair Canal Home w/ Pontoon Boat/Jet Ski's - Perfect for Families/Fishermen

Graber's River Getaway! Awesome freighter views -great work from home location.

10.0 out of 10, Exceptional, (73)
"Our stay was amazing, Tammi was great with all the useful information we needed she responded very quickly. We would definitely stay again. "
Graber's River Getaway! Awesome freighter views -great work from home location.

Newly-built modern farmhouse condo available in Grosse Pointe Park!

10.0 out of 10, Exceptional, (9)
"The property is located in a residential area and the accommodations look just like the photos online Great communication with owner it as chilly but I figured out the electric fireplace and it was very cosy I would recommend "
The price is AU$402
includes taxes & fees
7 Sept - 8 Sept
Newly-built modern farmhouse condo available in Grosse Pointe Park!

6-Bedrooms, 1.5-Bath Ranch Style Unit

2.0 star property
10.0 out of 10, Exceptional, (1)
"The host was amazing! So welcoming and very generous. He made our stay so much better, I could not recommend this or any of his properties enough! Thanks John! "
The price is AU$1,116
includes taxes & fees
7 Sept - 8 Sept
6-Bedrooms, 1.5-Bath Ranch Style Unit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterfield Hotel Reviews

Find out more about Chesterfield

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as AU$123 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Chesterfield has a good selection of restaurants. Make sure you have time to check out the shopping and entertainment choices during your trip.

What are some of the best holiday rentals that Chesterfield has to offer?

Full home, 420 friendly: This holiday home rental outside of Chesterfield is equipped with a selection of games, air conditioning and WiFi to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What’s there to see and do in Chesterfield?

Explore the area and family-friendly sights such as C.J. Barrymore's, or get out into nature at a spot like Metro Beach. Sycamore Hills Golf Club and Emerald Theatre are a couple of places you'll find in the wider area.

What’s a holiday rental in Chesterfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesterfield. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.