Holiday houses in Chesterfield

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Top-rated holiday rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Florence

4.93 out of 5 average rating, 15 reviews

“Cozy Escape | Relax & Recharge”

RicardoRating, 5 stars3 weeks ago

My stay at Kenneth’s Airbnb was absolutely wonderful! The space was spotless, beautifully decorated, and exactly as pictured—those emerald green chairs added a vibrant and luxurious touch! The kitchen was fully stocked and made it easy to prepare meals. Kenneth was an exceptional host—communicative, courteous, and made sure everything was in place for a smooth check-in and stay. The neighborhood felt safe and was conveniently located. I would absolutely recommend this spot to anyone visiting the area and would love to stay again in the future!

Top Guest favourite

Home in Plaza Midwood

5 out of 5 average rating, 11 reviews

Charming House in Charlotte!

VanceRating, 5 stars1 week ago

We stayed in Martha's home for 2 nights and it was a great place. The neighborhood was beautiful, and walkable to restaurants and groceries. It was peaceful and comfortable and we would definitely return for another stay. Martha was also very helpful after we had checked out, notifying us that we'd left something behind. She secured it for us until our daughter, who lives in Charlotte, could pick it up. 5 stars!

Guest favourite

Home in Charlotte

5 out of 5 average rating, 14 reviews

Spacious Getaway -Great Location

MichaelRating, 5 stars5 months ago

Staying here was a PERFECT place to enjoy the night while in Charlotte. The house was in a peaceful neighborhood and better than the description. Clean, spacious, and lots of individualized attention, even down to the candy waiting for us upon check-in. We loved it and are looking forward to coming back again next year!

Top Guest favourite

Holiday home in Pinehurst

4.98 out of 5 average rating, 51 reviews

Luxury Vacation Home "Lakeside in Pinehurst"

PaulRating, 5 stars1 month ago

This was our second stay at this beautiful house and we loved every minute of it. We caught lots of fish off the dock, ate family dinners on the deck, went for long walks around the neighborhood, played the Cradle while enjoying this meticulously clean and perfectly appointed house. Sondra and Jody were very responsive and very helpful!! We can’t wait for our next stay!!!

Top Guest favourite

Villa in Pinehurst

4.98 out of 5 average rating, 107 reviews

A Cozy Retreat on No. 5

BeverlyRating, 5 stars1 day ago

Very clean! Great location, close to lots of golf courses! Comfortable! My ladies foursome stayed for the third time and we will be back! Six people could stay very easily! You can practice putting too! Oh, and the deck has a lovely view too!

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Popular amenities for Chesterfield holiday rentals

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Other great holiday rentals in Chesterfield

Guest favourite

Guesthouse in Pinehurst

4.91 out of 5 average rating, 57 reviews

Sunny Pines Hideaway

MichaelRating, 5 stars1 week ago

The place looked better than the pictures and very clean . Carpenters really went all out making if feel like they put there heart into the build . If you want quiet this is the place

Guest favourite

Home in Mount Gilead

5 out of 5 average rating, 13 reviews

Lake Tillery escape

EmilyRating, 5 stars2 weeks ago

This was a phenomenal place to stay! John was very responsive and answered all my questions promptly. Would love to stay again in the future! Thanks again John!!

Guest favourite

Home in Matthews

4.91 out of 5 average rating, 80 reviews

Downtown Charm & Backyard Dream

HaleyRating, 5 stars3 days ago

We thoroughly enjoyed staying at Josh’s beautifully decorated home! Upon entering it smelt so good & instantly felt like home. The beds were extremely comfortable, we had everything we needed & there was plenty of space for all of us! Besides being near a busy road, the neighborhood was very quiet & peaceful. There were a few hiccups regarding the hot water accidentally being turned off under the kitchen sink & the dishwasher not working, but Josh was very quick to respond & compensate us for the trouble. He was also flexible on the check in time since we had to be somewhere earlier than the check-in. All in all it was a great home to stay in & I would definitely stay here again & recommend this house to others. Josh is a great host & very pleasant to do business with! :) highly recommend!

Guest favourite

Home in Southern Pines

4.95 out of 5 average rating, 39 reviews

The Oakmont Cottage

CaitlinRating, 5 stars1 month ago

Had a great weekend at Troy’s place while in town for a competition at the Carolina horse park! Only a 20 minute drive and very close to lots of great restaurants

Guest favourite

Home in Camden

5 out of 5 average rating, 8 reviews

Lakeside Views

NeilRating, 5 stars1 week ago

Brad’s lake house was perfect for our weekend. Great choice of bedrooms and places to gather, inside and outside. And the lake was peaceful and serene.

Superhost

Home in Great Falls

4.89 out of 5 average rating, 9 reviews

Beautiful home in Great Falls SC

SamuelRating, 5 stars1 month ago

Had a wonderful stay here with my fiance. Would recommend!

Guest favourite

Condo in Pinehurst

4.91 out of 5 average rating, 64 reviews

Pinehurst Golf, Weddings, Seminars with Hallmark A

TimRating, 5 stars4 weeks ago

Tim's place was welcoming and he was a responsive, available host. Check-in was smooth and easy. Check-in tips: If arriving at night, the lighting is low and condo unit numbers unobtrusive, so recommend having a good lighting source. Also, the condos are numbered sequentially up one side of the drive-way and down the opposite side v odds or evens all on one side as is typical in residential US. Tim's is toward the end on the left. Just a tip. Walking to town. Google will have you walking 1.5 miles back out of the development. But, if you go left out of the condo, walk to the end of the driveway, cross the green/fairway, you'll be on a main road that takes you directly to town, cutting a mile off the Google directions. Enjoy.

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