Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

The Corner Cottage with Private Fishing Pond

The Corner Cottage with Private Fishing Pond

Roland OK
Located in Roland, this vacation home is in a rural location, within a 15-minute drive of Cherokee Casino Roland and Fort Smith National Historic Site.
Opens in a new windowThe Corner Cottage with Private Fishing Pond
The vampire's den, downtown big house, pets ok

The vampire's den, downtown big house, pets ok

Fort Smith AR
The price is AU$215 per night from 27 Jan to 28 Jan
AU$215
27 Jan - 28 Jan 2026
includes taxes & fees
A stay at this vacation home places you in the heart of Fort Smith, within a 5-minute drive of Fort Smith Regional Art Museum and Clayton House.
Opens in a new windowThe vampire's den, downtown big house, pets ok
Water Tower Container-Beautiful views and surroundings-Secluded

Water Tower Container-Beautiful views and surroundings-Secluded

2 out of 5
Chester AR
The price is AU$255 per night from 28 Dec to 29 Dec
AU$255
28 Dec - 29 Dec
includes taxes & fees
Located in Mountainburg, this vacation home is in a rural location, within a 15-minute drive of Evans Trail Loop and Mountainburg City Park.
Opens in a new windowWater Tower Container-Beautiful views and surroundings-Secluded
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Charming 3-bedroom bungalow in delightful Fort Smith with WiFi, AC

Charming 3-bedroom bungalow in delightful Fort Smith with WiFi, AC

Fort Smith AR
With a stay at this vacation home in Fort Smith, you'll be within a 5-minute drive of Sparks PremierCare and Hillcrest Park.
Opens in a new windowCharming 3-bedroom bungalow in delightful Fort Smith with WiFi, AC
StarLab '86 -Downtown Pet Friendly

StarLab '86 -Downtown Pet Friendly

Fort Smith AR
The price is AU$193 per night from 27 Jan to 28 Jan
AU$193
27 Jan - 28 Jan 2026
includes taxes & fees
A stay at this vacation home places you in the heart of Fort Smith, within a 5-minute drive of Fort Smith Regional Art Museum and Clayton House.
Opens in a new windowStarLab '86 -Downtown Pet Friendly
Mi Casita Cottage in Park Hill Fort Smith

Mi Casita Cottage in Park Hill Fort Smith

Fort Smith AR
The price is AU$292 per night from 4 Jan to 5 Jan
AU$292
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at this vacation home in Fort Smith, you'll be within a 5-minute drive of Hillcrest Park and Sparks PremierCare.
Opens in a new windowMi Casita Cottage in Park Hill Fort Smith
The Foster Branch House- Charming 3-BR house in Van Buren, near I-40 & Ft. Smith

The Foster Branch House- Charming 3-BR house in Van Buren, near I-40 & Ft. Smith

Van Buren AR
The price is AU$326 per night from 5 Jan to 6 Jan
AU$326
5 Jan - 6 Jan 2026
includes taxes & fees
Located in Van Buren, this vacation home is within a 15-minute drive of Baptist Health-Van Buren and Alma Walking Trail.
Opens in a new windowThe Foster Branch House- Charming 3-BR house in Van Buren, near I-40 & Ft. Smith
Cozy Cove-Cute 3BR in Town

Cozy Cove-Cute 3BR in Town

Van Buren AR
Located in Van Buren, this vacation home is within a 10-minute drive of Baptist Health-Van Buren and Kay Rodgers Park.
Opens in a new windowCozy Cove-Cute 3BR in Town
Pirate Seeking crew. Downtown with hot tub!

Pirate Seeking crew. Downtown with hot tub!

fort smith AR
The price is AU$193 per night from 27 Jan to 28 Jan
AU$193
27 Jan - 28 Jan 2026
includes taxes & fees
A stay at this vacation home places you in the heart of Fort Smith, within a 5-minute drive of Fort Smith Regional Art Museum and Clayton House.
Opens in a new windowPirate Seeking crew. Downtown with hot tub!
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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.

Chester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chester vacation homes are the perfect way for you to wing it.

Holiday houses in Chester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chester Holiday Homes essential information

Accommodation
89 Holiday Homes
Lowest Price
AU$129
Highest Price
AU$326
Popular accommodation
The Corner Cottage with Private Fishing Pond, The vampire's den, downtown big house, pets ok, Water Tower Container-Beautiful views and surroundings-Secluded, Charming 3-bedroom bungalow in delightful Fort Smith with WiFi, AC, StarLab '86 -Downtown Pet Friendly, Mi Casita Cottage in Park Hill Fort Smith, The Foster Branch House- Charming 3-BR house in Van Buren, near I-40 & Ft. Smith, Cozy Cove-Cute 3BR in Town, Pirate Seeking crew. Downtown with hot tub!

Top trending hotels in Chester

Beard and Lady Inn

Beard and Lady Inn

3 out of 5
411 E Front Ave Chester AR
Located in Chester, Beard and Lady Inn is in a rural location, a 4-minute drive from Ozark National Forest and 6 minutes from Evans Trail Loop.
Opens in a new windowBeard and Lady Inn
Beautiful modern cabin on top of the mountain with stunning sunset views.

Beautiful modern cabin on top of the mountain with stunning sunset views.

Chester AR
The price is AU$319 per night from 5 Jan to 6 Jan
AU$319
5 Jan - 6 Jan 2026
includes taxes & fees
Located in Chester, this cabin is on a river, a 5-minute drive from Ozark National Forest and 7 minutes from Evans Trail Loop.
Opens in a new windowBeautiful modern cabin on top of the mountain with stunning sunset views.
Cherokee Casino & Hotel Roland

Cherokee Casino & Hotel Roland

3.5 out of 5
109 Cherokee Boulevard Roland OK
The price is AU$140 per night from 28 Dec to 29 Dec
AU$140
28 Dec - 29 Dec
includes taxes & fees
Located in Roland, Cherokee Casino & Hotel Roland is a 1-minute drive from Cherokee Casino Roland and 8 minutes from Bass Reeves Statue.
Opens in a new windowCherokee Casino & Hotel Roland
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The ARC Hotel

The ARC Hotel

2.5 out of 5
6813 Phoenix Ave Fort Smith AR
Fully refundableReserve now, pay when you stay
The price is AU$129 per night from 28 Dec to 29 Dec
AU$129
28 Dec - 29 Dec
includes taxes & fees
With a stay at The ARC Hotel in Fort Smith, you'll be within a 5-minute drive of Mercy Clinic Convenient care and Advance Care Hospital-Ft Smith.
Opens in a new windowThe ARC Hotel
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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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^Subject to availability and chosen travel dates.