Vacation rentals in Chester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chester

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

Guest favorite

Guesthouse in Matthews

4.97 out of 5 average rating, 145 reviews

The Dwellington.Private.Cozy.Convenient.Walkable.

⭐A Hidden Gem tucked away on a dead end St. in an est. NBD of Historic DT Matthews! The Dwellington has Southern charm w/ a wrap around covered patio, a screened-in porch & a garden view! This spacious guest house has 9ft ceilings, a well thought out floor plan & a relaxing spa like bath. Easy walk to shop, sip, & dine! Come experience all our adorable Town has to offer! Small Town feel with Big City convenience! MULT ways to drive or ride to UPT CLT in less than 25 minutes. Book now and enjoy!

Jul 11 – 18

$90 per night
Guest favorite

Home in Waxhaw

4.98 out of 5 average rating, 532 reviews

Fox Farms Little House

Fox Farms Little House is the perfect place to unplug from your busy life...located on a horse farm in Waxhaw, it is a peaceful retreat for a couple looking for relaxation and a beautiful setting. Whether you are walking the 155 acres of trails, relaxing with a good book on the porch, or enjoying the many animals on the property, you will leave here recharged and refreshed. Minutes from downtown Waxhaw, Monroe, and 20 minutes to Ballantyne and Waverly, the Little House is close to everything.

Jun 21 – 28

$87 per night
Guest favorite

Home in Rock Hill

4.93 out of 5 average rating, 189 reviews

1800s Cabin on Holland Acres - Getaway or gather

Step back in time in a 1800s roadside cabin on four acres. Grill on the back deck, relax in the hot tub, soak in the claw foot tub and simply enjoy the serenity. Cabin has a full kitchen, two baths, and main floor & loft sleeping areas. You'll be minutes from downtown Rock Hill and the Event Center, restaurants, parks, & Winthrop Univ. Rural setting makes a perfect families & pets getaway; unique features make it great for gathering! Come enjoy this quaint piece of history & prepare to unwind!

Jun 13 – 20

$118 per night

Popular amenities for Chester vacation rentals

Stay near Chester's top sights

Italian Garden Of Chester3 locals recommend
BI-LO3 locals recommend
Arts Council of Chester County3 locals recommend

Other great vacation rentals in Chester

Guest favorite

Tiny home in Clover

4.91 out of 5 average rating, 101 reviews

Tranquility on 2 acres in an authentic tiny house!

Feb 6 – 13

$119 per night
Guest favorite

Guesthouse in Rock Hill

4.98 out of 5 average rating, 105 reviews

Cove Cottage, Lakefront Retreat + Kayaks

Oct 5 – 12

$109 per night
Guest favorite

Home in Chester

4.8 out of 5 average rating, 20 reviews

Great 3 bd/1bath brick home with the essentials

Jul 21 – 28

$84 per night
Guest favorite

Apartment in Rock Hill

5.0 out of 5 average rating, 23 reviews

Spacious Cottage with Salt water pool and Hot tub

Aug 27 – Sep 3

$99 per night
Guest favorite

Apartment in Chester

5.0 out of 5 average rating, 12 reviews

Historic apartment in downtown Chester

Jan 4 – 11

$265 per night
Guest favorite

Apartment in Waxhaw

4.92 out of 5 average rating, 53 reviews

Jud's place

Jul 26 – Aug 2

$94 per night
Guest favorite

Home in Carlisle

4.89 out of 5 average rating, 18 reviews

Cozy, Beautiful, Cottage House.

Aug 16 – 23

$70 per night
Superhost

Apartment in Lancaster

4.83 out of 5 average rating, 30 reviews

Cozy Townhouse in Lancaster 5 min MUSC

Aug 22 – 29

$83 per night
Guest favorite

Home in Smyrna

4.91 out of 5 average rating, 45 reviews

Private 2 Bedroom 2 Bath Country Home

Sep 5 – 12

$95 per night
Guest favorite

Home in Rock Hill

4.86 out of 5 average rating, 14 reviews

Contemporary 2 Bed Bungalow * Great Location *

Jul 8 – 15

$72 per night
Guest favorite

Cottage in Blacksburg

5.0 out of 5 average rating, 20 reviews

Cozy Country Cottage on Wooded Lot.

May 15 – 22

$64 per night
Guest favorite

Apartment in Rock Hill

4.95 out of 5 average rating, 65 reviews

1-bedroom at Winthrop gate near Sports & Event Ctr

Aug 26 – Sep 2

$83 per night

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