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$249 per night from 17 Feb to 18 Feb
AU$249
17 Feb - 18 Feb
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$241 per night from 11 Feb to 12 Feb
AU$241
11 Feb - 12 Feb
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
The price is AU$253 per night from 9 Mar to 10 Mar
AU$253
9 Mar - 10 Mar
includes taxes & fees
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$184 per night from 15 Feb to 16 Feb
AU$184
15 Feb - 16 Feb
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$277 per night from 11 Feb to 12 Feb
AU$277
11 Feb - 12 Feb
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$309 per night from 16 Feb to 17 Feb
AU$309
16 Feb - 17 Feb
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$168 per night from 11 Feb to 12 Feb
AU$168
11 Feb - 12 Feb
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
87 Holiday Homes
Lowest Price
AU$148
Highest Price
AU$309
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

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$299 per night from 11 Feb to 12 Feb
AU$299
11 Feb - 12 Feb
includes taxes & fees
With a stay at this cabin in Chester, you'll be on a river, within a 10-minute drive of Ozark National Forest and Evans Trail Loop.
Opens in a new windowBeautiful modern cabin on top of the mountain with stunning sunset views.
Beard and Lady Inn

Beard and Lady Inn

3 out of 5
411 E Front Ave Chester AR
The price is AU$153 per night from 12 Mar to 13 Mar
AU$153
12 Mar - 13 Mar
includes taxes & fees
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
Old Cross Roads Cabin 3 bed/2 bath

Old Cross Roads Cabin 3 bed/2 bath

Chester AR
With a stay at Old Cross Roads Cabin 3 bed/2 bath in Chester, you'll be 11.8 mi (19 km) from Ozark National Forest and 9.5 mi (15.2 km) from Devil's Den State ...
Opens in a new windowOld Cross Roads Cabin 3 bed/2 bath
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Cherokee Casino & Hotel Roland

Cherokee Casino & Hotel Roland

3.5 out of 5
109 Cherokee Boulevard Roland OK
The price is AU$148 per night from 22 Feb to 23 Feb
AU$148
22 Feb - 23 Feb
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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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.