Holiday rentals in Grayson County

Cliffside Cottage

Welcome to your private escape in the woods! Nestled in a quiet, secluded setting with a scenic views and gated entry, the home feels like a true retreat while offering upscale amenities. Relax by the private heated pool surrounded by expansive concrete decking, and 2 put-put courses. Outdoor lounge and seating areas ideal for morning coffee or sunset cocktails. Gas grill, and umbrellas by the pool, this home has it all! Age must be 25 yrs+ to book. No more that 6 guests on property at any time.

Location · Family · Hospitality

The Woodcroft Ranch • Mid Century Near THF & TMC

The Woodcroft Ranch is a bold 1969 mid century retreat in Denison, TX that blends its original, retro character with modern comfort. Overlooking the former Woodlawn Golf Course, this spacious 3,100 sqft home offers peaceful surroundings, large gathering spaces, and a relaxed atmosphere ideal for families, traveling medical professionals, tournament weekends, and Lake Texoma getaways. Huge fenced yard perfect for kids and dogs. Minutes from TMC Hospital, THF Park, Downtown Denison, and the lake.

Location · Family · Quiet

21-Acre Retreat | Pond, Trails, Bridges & Gym

Unplug, unwind, & enjoy nature at this charming 2-bedroom barndo tucked away on 21 acres in Whitesboro, TX. Full kitchen, spacious living room, private cozy fire pit, & scenic surroundings—oak trees, pond, trails, & bridges. This retreat is perfect for couples, families, or friends looking to relax and recharge. Private gym and game room included. Whether you're looking for a weekend getaway, a creative retreat, or just a quiet place to relax, "Falling Leaf Ranch" has everything you need.

Value · Location · Amenities

Countryside Manor with Pool

Relax, unwind and recharge at our beautiful countryside manor that sits on 20 acres. Located 4 miles from Choctaw Casino and 4 miles from Lake Texoma! Chefs kitchen to feed the masses. 3 beds and 2.5 baths Pool with patio to entertain you and your guests. Traeger grill for all your bbq needs. Horses, pups and chickens roam freely. DISCLAIMER: Our property manager lives in the back house 100 yards from the house. You will have your privacy, but is there for any immediate needs.

Family · Location · Grill

Fun & Modern Texoma Retreat-Near Highport Marina!

Experience Lake Texoma in style from the modern comfort of “Tanglewood Hideaway”! This open, airy, freshly remodeled 4-bedroom home, with a contemporary retro style, is located 1-mile from the lake. Highport Marina, Tanglewood Golf Course and lively lakeside dining are a 5-minute drive away! With 2 living areas, a large dining area for 12, ping pong table, 4 Smart TVs and a deck overlooking a private wooded lot, this home is the perfect retreat for groups of friends or family!

Family · Location · Accuracy

Peg’s Place

Come enjoy a taste of Texas in our well decorated haven. Excellent for travel nurses- just 5 minute from Texoma Medical center. Enjoy the historic downtown Denison with shopping, restaurants, wineries and pubs. Waterloo Lake Park is 5 minutes away with playgrounds, hiking, fishing and kayaking. Lake Texoma is 15 minutes for fishing, boating and hiking. Choctaw Casino- 20 minutes. WindStar Casino - 60 minutes. You are guaranteed to make lasting memories at this unique place

Value · Family · Parking

Barndominium with the OK View

Large luxurious barndominium in a beautiful country setting right outside of the city limits. This 2,400 sqft space is open concept with full kitchen, one full size bathroom, living area, dining table, washer/dryer, ping pong table and sleeping loft. The loft has two twin size bunk beds and two private queen size bedrooms off to either side. This property is shared with two other Airbnb rentable units with a large private pond down below with shared dock. No parties or events.

Location · Value · Pool

Experience Lake Texoma Spacious 4Bed Vacation Home

Your home away from home in popular Soldier Creek. Come back to relax after a long day out on Lake Texoma. 5 minutes from Marina DelRay/Barbay with live music, dancing, food trucks. 15 minute drive to beautiful Chickasaw Pointe Golf course. Fishing guides are 15 minutes away. Full kitchen with outdoor griddle for cooking when you get back. 4 bedrooms, 5 beds with large patio and furniture. All the amenities you need to sleep well and stay comfortable while you stay.

Location · Family · Decor

Lake O'Clock: Pool, firepit, outdoor movies

Spring is in the air! Pool is open! Enjoy an evening around the fire pit with an outdoor movie under the stars. We are close to many marinas and casinos. Large wrap around porch. Play a game of corn hole, horse shoes, or giant connect four while enjoying the 3 acres of outdoor space. Less than 1 mile to the sandy beach of Lake Texoma. Stand up paddle boards are available for use. Truck or small SUV needed to transport lake items. Board games and children’s toys inside

Family · Location · Checkout

Wildwood Ranch- Pool, Media Rm, Sport Ct on 160 ac

Get away from it all at Wildwood Ranch! The 3,600 square foot ranch house has recent updates with an open concept kitchen/dining/living, perfect for groups. The beautifully-decorated 4 bedrooms and 4.5 bathrooms will welcome you home after exploring the 160 acres of natural beauty! Take a dip in the sparkling pool, fish the ponds, hike miles of trails or relax by the campfire at night. Come enjoy some peace and quiet in the country- you may not want to leave!

Family · Value · Hospitality

Texas Rock Casita with Incredible Ranch Views

Welcome to Rock Casita South, Casita 2. Take it easy at this unique and tranquil getaway. Come escape to Abney Ranch. Our custom casitas are located on a working ranch, nestled in the trees. You'll have access to 10 of your own private acres equipped with fishing, hiking, a pond, a fire pit, hammocks, yard games, and much more! Come relax and unwind from your day-to-day routine. Our space is perfect for Wedding Stays as local wedding venues are close by!

Family · Location · Amenities

"The Little Ass Apartment!"

Welcome to "The Little Ass Apartment" which sits on 28 acres with 3 mini donkey hosts. This apartment has everything you will need to relax indoor or out. There is a full kitchen, living room, bathroom, washer/dryer, and spacious bedroom. Outside has a large fenced in yard, fire pit with seating, and a wrap around porch with views of the sunrise and sunset! Enjoy the backyard entertainment area with washers and corn hole!

Value · Family · Checkout