Search Holiday Rentals in Chesterfield

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Chesterfield

Affordable Suites of America Detroit-Warren

3.0 star property
7.4 out of 10, Good, (1331)
"Enjoyed my stay for the evening "
The price is £60
includes taxes & fees
31 Jul - 1 Aug
Affordable Suites of America Detroit-Warren

Full home, 420 friendly

9.0 out of 10, Wonderful, (9)
"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 £242
includes taxes & fees
31 Jul - 1 Aug
Full home, 420 friendly

The Harsens Island Retreat

9.2 out of 10, Wonderful, (5)
"We all had a much needed restful weekend,this house was perfect for! Thank you"
The Harsens Island Retreat

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

9.2 out of 10, Wonderful, (19)
"Everything about this stay was seamless and easy. Thank you so much!"
Home in Royal Oak w/ pool & sauna & dream garage

Air-Conditioned Studio | Pool

9.4 out of 10, Exceptional, (13)
"Nice spot. Room was clean but the bathroom was small. Pool and hot tub was good. Overall a 4 out of 5. "
Air-Conditioned Studio | Pool

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
8.6 out of 10, Excellent, (9)
"Place was amazing , stay was great exactly like picture "
The price is £123
includes taxes & fees
31 Jul - 1 Aug
Evanston BnB

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 £550
includes taxes & fees
3 Aug - 4 Aug
6-Bedrooms, 1.5-Bath Ranch Style Unit

Lake St Clair Waterfront

8.8 out of 10, Excellent, (11)
"great place to stay and fish lake St. Clair"
Lake St Clair Waterfront

Lake St Clair Waterfront Fisherman Welcome

2.0 star property
5.0 out of 10, (2)
"We were in town for a wedding and this trailer was perfect! Right on the water if you have a boat it’s great! We fished off the dock. It was quiet. Easy to get to. Owner was very nice and accommodating. "
Lake St Clair Waterfront Fisherman Welcome

Spacious 4 Bed Room Haven in Clawson Near Bham

5.2 out of 10, (10)
"Property served our purposes. Spacious 4 bedrooms and nice neighborhood"
The price is £232
includes taxes & fees
3 Aug - 4 Aug
Spacious 4 Bed Room Haven in Clawson Near Bham

private and spacious

10.0 out of 10, Exceptional, (71)
"This property is in a great location for enjoying Rochester's amazing downtown. It's a very comfortable home like setting with a gracious host."
The price is £100
includes taxes & fees
2 Aug - 3 Aug
private and spacious

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

9.6 out of 10, Exceptional, (75)
"The hosts were very nice and we enjoyed our stay"
St.Clair Canal Home w/ Pontoon Boat/Jet Ski's - Perfect for Families/Fishermen

The Harperwood's Haven

9.4 out of 10, Exceptional, (18)
"We really enjoyed our stay and appreciate the partnership with the owner, Keynote."
The price is £185
includes taxes & fees
31 Jul - 1 Aug
The Harperwood's Haven

420 friendly Charming 3-bedroom house in awesome Detroit with AC, WiFi

7.0 out of 10, Good, (2)
"Lori was helpful and very friendly. "
420 friendly Charming 3-bedroom house in awesome Detroit with AC, WiFi

Saint Clair River front Retreat With 6 Beds - Enjoy Fishing-Kayak-Relax

10.0 out of 10, Exceptional, (1)
"Seven of us stayed there. My girlfriend drove there. My buddy and his family drove there. My daughter and I arrived by boat. Having a boathouse was very cool that I didn't have to cover my boat. The view was amazing. Upstairs master bedroom is very roomy. There's a dollar store and a Kroger within a mile of the property that has everything you can get food, toys supplies. The kids like d going to dairy Queen on their bikes. Overall it was a property that I will visit again, great communication...
The price is £463
includes taxes & fees
3 Aug - 4 Aug
Saint Clair River front Retreat With 6 Beds - Enjoy Fishing-Kayak-Relax

SelfieBnb | Great for Content Creation & Selfies

10.0 out of 10, Exceptional, (11)
"Super great place"
The price is £242
includes taxes & fees
31 Jul - 1 Aug
SelfieBnb | Great for Content Creation & Selfies

Charming old farmhouse, spacious 2-bedroom on 2+ acres

7.4 out of 10, Good, (3)
"Charming Farmhouse Stay Near Big Red OrchardWe stayed at this beautifully renovated farmhouse while attending a wedding at Big Red Orchard — just 8 minutes away — and it was perfect for our weekend. The home is tastefully updated, with a large yard and frequent visits from local wildlife, which made the setting feel peaceful and relaxing.It was a very comfortable stay, and we honestly don’t understand the negative review left by the previous guest — our experience was completely different. The...
The price is £223
includes taxes & fees
5 Aug - 6 Aug
Charming old farmhouse, spacious 2-bedroom on 2+ acres

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

9.8 out of 10, Exceptional, (7)
"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! "
The price is £270
includes taxes & fees
26 Aug - 27 Aug
Charming 2-bedroom cottage with WiFi, AC on a peaceful Harsens Island canal.

Charming 3-bedroom house with AC, WiFi in awesome Detroit

8.0 out of 10, Very good, (1)
"We enjoyed our stay and the house was comfortable. Could've used hand towels in the kitchen and ice trays with cubes. Appreciated the professionalism of the host and the cleanliness of the property. "
The price is £306
includes taxes & fees
12 Aug - 13 Aug
Charming 3-bedroom house with AC, WiFi in awesome Detroit
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesterfield Hotel Reviews

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.