Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

The VB Haven

The VB Haven

Van Buren AR
The price is AU$380 per night from 26 May to 27 May
AU$380
26 May - 27 May
includes taxes & fees
Located in Van Buren, this vacation home is a 4-minute drive from Baptist Health-Van Buren and 7 minutes from Arkansas River.
Opens in a new windowThe VB Haven
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 17 May to 18 May
AU$193
17 May - 18 May
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!
West Fork Pool and Hot Tub- 10 mins to Fay, Devils Den

West Fork Pool and Hot Tub- 10 mins to Fay, Devils Den

West Fork AR
With a stay at this vacation home in West Fork, you'll be in the mountains, within a 15-minute drive of University of Arkansas and Arkansas Air Museum.
Opens in a new windowWest Fork Pool and Hot Tub- 10 mins to Fay, Devils Den
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Retreat to the Peak

Retreat to the Peak

Winslow AR
When you stay at this vacation home in Winslow, you'll be in the mountains and 9 minutes by car from Ozark National Forest.
Opens in a new windowRetreat to the Peak
StarLab '86 -Downtown Pet Friendly

StarLab '86 -Downtown Pet Friendly

Fort Smith AR
The price is AU$178 per night from 19 May to 20 May
AU$178
19 May - 20 May
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
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$246 per night from 17 May to 18 May
AU$246
17 May - 18 May
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
Lovely 2-bedroom triplex unit with AC in charming Van Buren.

Lovely 2-bedroom triplex unit with AC in charming Van Buren.

Van Buren AR
The price is AU$207 per night from 18 May to 19 May
AU$207
18 May - 19 May
includes taxes & fees
Located in Van Buren, this vacation home is within a 10-minute drive of Alma Town Hall and Alma Public Library.
Opens in a new windowLovely 2-bedroom triplex unit with AC in charming Van Buren.
My house your house

My house your house

Fort Smith AR
The price is AU$364 per night from 18 May to 19 May
AU$364
18 May - 19 May
includes taxes & fees
Located in Fort Smith, this vacation home is within a 15-minute walk of Baptist Health-Fort Smith and Sparks PremierCare.
Opens in a new windowMy house your house
Lolli's Lil Getaway

Lolli's Lil Getaway

Alma AR
Located in Alma, this vacation home is within a 10-minute drive of Clear Creek Public Use Area and Clear Creek Park.
Opens in a new windowLolli's Lil Getaway
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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
93 Holiday Homes
Lowest Price
AU$127
Highest Price
AU$380
Popular accommodation
The VB Haven, Pirate Seeking crew. Downtown with hot tub!, West Fork Pool and Hot Tub- 10 mins to Fay, Devils Den, Retreat to the Peak, StarLab '86 -Downtown Pet Friendly, Charming 3-bedroom bungalow in delightful Fort Smith with WiFi, AC, Lovely 2-bedroom triplex unit with AC in charming Van Buren., My house your house, Lolli's Lil Getaway

Top trending hotels in Chester

Beard and Lady Inn

Beard and Lady Inn

3 out of 5
411 E Front Ave Chester AR
The price is AU$150 per night from 17 May to 18 May
AU$150
17 May - 18 May
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
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$310 per night from 19 May to 20 May
AU$310
19 May - 20 May
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.
Cherokee Casino & Hotel Roland

Cherokee Casino & Hotel Roland

3.5 out of 5
109 Cherokee Boulevard Roland OK
The price is AU$127 per night from 17 May to 18 May
AU$127
17 May - 18 May
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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Wyndham Fort Smith City Center

Wyndham Fort Smith City Center

4 out of 5
700 Rogers Ave Fort Smith AR
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 24 May to 25 May
AU$156
24 May - 25 May
includes taxes & fees
When you stay at Wyndham Fort Smith City Center in Fort Smith, you'll be connected to the convention center, within a 10-minute walk of Fort Smith National Historic ...
Opens in a new windowWyndham Fort Smith City Center
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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.

Top Picks

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^Subject to availability and chosen travel dates.