
Holiday houses in Chester
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Top-rated holiday rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness and more.

Lone Wolf Lodge Cabin Rental
Lone Wolf Lodge is located at the entrance of Big Thicket National Preserve, Woodlands Trail, where you have 14,000 acres to explore. Whether you like to walk, bike, fish or just relax this area can accommodate almost any outdoor activity. We are a short 2.5 mile drive away from the Luckiest Spot in Texas, The Naskila Casino, where you can enjoy endless gaming and delicious food. At our Lone Wolf Cabin you can also enjoy roasting marshmellows over the fire pit or a movie night in the loft. Our cabin provides more than just your average stay at a hotel. Come out and see what it's like to stay by the park!
FamilyLocationBarbecue
4.93 out of 5 average rating, 167 reviews
Private 50 Acres Lake Sam Rayburn
Settle into 50 private acres in East Texas near Lake Sam Rayburn. Whether you’re here for a longer stay, traveling for work, a fishing trip, a family getaway, or a weekend with friends, Camplee offers a comfortable home base that feels more like home than a rental. Surrounded by national forest, enjoy complete privacy, a stocked fishing pond, scenic trails, Starlink Wi-Fi, fire pits, covered pavilions, outdoor soaking tubs, a jacuzzi bathtub, and more. The nearest boat ramp just 10 minutes away.
FamilyLocationHiking
5.0 out of 5 average rating, 122 reviews
Lakefront Home with Dock, Kayaks, and Paddleboard
Located just 2 hours from Houston, our little lake house retreat is the perfect getaway. Whether you enjoy sitting around the fire with family and friends, hitting the lake for fishing, kayaking, paddleboarding, or just lounging on the large floating water mat, we have you covered. At the end of the day, fire up the Traeger grill or Traeger Flatrock griddle and enjoy dining out on the deck while taking in the amazing views of the lake as the sun goes down. Come on out and make some memories!
FamilyLocationOutdoor spaces
4.9 out of 5 average rating, 133 reviews
Lakefront Sam Rayburn modern home - amazing views!
Enjoy nature in this luxury lakefront modern guest house in the treetops with fantastic views of Lake Sam Rayburn and the Angelina National Forest. You will have the entire private living space, including your own living room, bedroom, kitchen, full bathroom and 4 decks. Be sure to take a swim in the lake from the sandy beach. Bring your boat: this property is 15 minutes from Umphrey Pavilion and only 1 mile from Sandy Creek Boat Ramp. You are welcome to fish anywhere on the property.
ValueLocationBathroom
4.98 out of 5 average rating, 179 reviews
Clean, Furnished 3BR Home Convenient Location
Very clean 3-bedroom Woodville home located in town. Hosted by experienced host with 98 positive reviews. Comfortable, safe, immaculately clean, cold AC, convenient, and peaceful. All memory foam mattresses and pillows, smart TV in every room, 75” TV in living room, fully stocked full size kitchen. 1 mile from Woodville schools, 3 miles from the rodeo arena and fairgrounds, 2 miles from the courthouse square, 15 miles to Big Thicket National Park hiking, 30 miles to Sam Rayburn.
LocationFamilyComfort
5.0 out of 5 average rating, 8 reviews
90 minutes N. of Houston, Private, pet friendly
Quiet country setting nestled in the trees. Enjoy your stay in our 2018 modern cabin on 30 acres in the piney woods. Sip your favorite beverage rocking on the enormous porch while your steaks are cooking on the grill. At night you can gather around the lower fire pit and stargaze. It is unlikely you will encounter anyone unless you venture out for walk down to one of the neighboring farms. The cottage has super high speed internet. Make video calls without buffering.
ValueFamilyBackyard
5.0 out of 5 average rating, 135 reviews
Mirror House · Sauna+Hot Tub · On Lake Livingston
Experience the intersection of high-end architecture and raw nature. This mirror-clad sanctuary is designed to disappear into its surroundings. The only mirror house built directly on Lake Livingston, offering an immersive escape for couples and solo travelers. Step outside to three levels of deck, Wellness deck with hot tub + cold plunge, a lakefront fire pit, and direct water access. Just 90 minutes from Houston—a curated space where minimalism meets the forest.
LocationFamilyQuiet
4.97 out of 5 average rating, 29 reviews
Horner’s Lake House
We are 5 miles from beautiful lake Sam Rayburn. You can fish all day or evening, come home to a fish cleaning station for your catch. Plenty of room to park and charge your boat to be ready for the next day. Private deck/grill and sitting if you choose to cook your meal. Clean hot shower. Living area very clean with large screen TV/movies or books if you choose to read. Queen size bedding for a great nights rest. Very quiet with only the cows, birds and squirrels
LocationValueTV
4.94 out of 5 average rating, 218 reviews
Rooster Tail Resort
Quaint studio guest house located on a private 2 mile lake, ideal for all boating activities including fishing, water skiing or just soaking up the sun. This property is secluded under a shaded canopy of oaks, in a quiet, country setting. A fire pit, BBQ area, swim area and dock, which is fitted with cleats for docking your boat or jet skies, are available for use. Plenty of parking. Pets under 20lbs are allowed with PRE-APPROVAL BEFORE BOOKING ONLY.
FamilyLocationTV
4.99 out of 5 average rating, 215 reviews
Just Chillin by the Lake
Relax and enjoy the beauty of this peaceful private lake with lakefront cabin. Full kitchen, with complimentary coffee and tea, queen bed, private full bathroom. A large, covered porch. Fire pit and charcoal grill are provided as well as a Kayak for your enjoyment. Kayak, fish, or swim or just chill on private pier. Check in 3:00 pm - Check out 11:00 am. If there is anything else you would like, we can try and make it happen. Just ask.
ValueLocationBarbecue
4.95 out of 5 average rating, 152 reviews
Vicker’s Ranch 10 min from Casino Welcome Home
Relax with the whole family at this peaceful place to stay. Pool table available. Close to Naskila Casino, lake Donna, Antique Shops, restaurants and Lake Tombigbee Campground. HOUSE AND FENCED AREA AROUND HOUSE ONLY . BBQ Grill in red shed. Dollar general and family dollar within walking distance. The rock shop is within five minutes drive.
ValueLocationOutdoor spaces
5.0 out of 5 average rating, 17 reviews
The Farm House
Relax with the family at this peaceful place to stay on a secluded cleared 3 acres. Have your morning coffee on the back porch and watch the sun rise. Enjoy and evening sunset on the front porch. Events are welcomed but advanced notice and additional pricing will be incurred. Please send inquiries to host prior to booking.
LocationFamilyQuiet
4.92 out of 5 average rating, 182 reviewsPopular amenities for Chester holiday rentals
Other great holiday rentals in Chester

The Ponderosa
FamilyValueLayout
5.0 out of 5 average rating, 34 reviews
Tiny Timbers Livingston
LocationFamilyParks
4.95 out of 5 average rating, 62 reviews
Fenced | 90m from Houston | 7 Acres | Dog Friendly
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4.97 out of 5 average rating, 31 reviews
Country Home, 4 Bed, 3.5 Bath, Pet Friendly
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5.0 out of 5 average rating, 34 reviews
'Paradise' on the lake
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5.0 out of 5 average rating, 51 reviews
Lufkin Comfort & Convenience | Cozy 2BR Near DT
LocationFamilyComfort
4.98 out of 5 average rating, 46 reviews
Lakefront King Rooms | Views | Cowboy Pool +Cinema
LocationFamilyCondition
5.0 out of 5 average rating, 47 reviews
Lakewood Lodge - 5BR+ Pool Table +Hot Tub+ More!
FamilyLocationHospitality
5.0 out of 5 average rating, 14 reviewsDestinations to explore
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