Cottage holiday rentals in Montgomery

Entire Cottage Getaway | Pond • Fire Pit • Deck

Escape to the serene beauty of Blue Pond Retreat! Nestled on 8 wooded acres, this charming cottage offers relaxation and rejuvenation. Enjoy a spring-fed pond, fire-pit, and lush surroundings. The main cottage features a cozy queen bedroom, stylish living area, full bath, and a fully stocked kitchen. A separate private suite, connected by a wood deck, adds a full-size bed and bath. Perfect for couples, friends, or families, it’s your ideal countryside escape under starry skies. Near Lake Conroe.

Magnolia Cottage/Near Renaissance Festival

Newly remodeled, spacious country cottage on eight acres. Beautiful stone barrel kitchen, open floor plan living room, breakfast area, formal dining room area to spend time with the family. New furniture in the common areas and in the primary room. Luxurious master bathroom and extra full bath. Stay includes clean linens, towels toiletries, WIFI, TV, full kitchen, washer & dryer, and two-car garage. Extra fees will be added if pet damage any area or to do an extra clean. Pet fee $75 under 50lbs.

The Canal House

Our little getaway sits on a canal that leads into Lake Conroe. The marina at the lake offers jet skis and boats for rent. Our house comes with a canoe and a kayak. It also offers fishing in the canal. Very quiet, serene place with lots of beautiful birds. We particularly like to sit on the back porch and watch the egrets fly by or the ducks swimming in the canal. Perfect place for respite and recharge, or ramp it up and go jet skiing on the lake. Or both! This is a non-smoking home.

The Cottage at Pine Lake

Take a break & unwind at this peaceful oasis. Kayak, catch a fish, take a swim in the pool across the street or just relax on the front deck and watch the birds. Great location on private lake with pier. Close to local Montgomery wedding venues( Lumineer 2 min, Pine Lake Ranch 5min) Short drive to Margaritaville resort. Spend the day on beautiful Lake Conroe, bring your boat/ jet ski and launch down the road at the marina. Short drive to Sam Houston national forest to enjoy nature and hiking

Charming 1933 farmhouse

Welcome to our farmhouse, This beautiful home is full of small town charm and character. Come visit the small historic town of tomball and stay in a home just as special as the town it’s self. We strive to provide our guests with the best possible stay by providing everything we possibly could think of you needing. This home is right outside of town on Main Street. The home is 2 bedrooms 1 bath, the bathroom is a jack and Jill between the bedrooms. Dogs are welcome but there is a 35 per dog.

The Dairy Barn & Parlor

Set on 12 acres this secluded little house is the perfect get-a-way place to enjoy some down time. Close to fishing at Lake Conroe this cottage serves also as a central point to enjoy some of the local wineries, visit historic downtown Montgomery, explore the Sam Houston National Forest or spend time at the Texas Renaissance Festival which is only 20 minutes away. The physical address and entrance road name has changed several times in the past few years so the GPS address may not work.

Lily Pad/Lake Front/Fire Pit/Lake Swimming Access

Imagine ending your day on the rap around deck, watching the sun melt into the peaceful, glassy lake. Earlier, you were out on the kayaks, kids laughing and floating on the lily pad, or cooling off at the private country club pool (pool fee applies) As night settles in, you’re gathered by the fire pit, roasting s’mores and sharing stories under a glowing sky — no rush, just stillness, laughter, and connection. This is where time slows down, hearts reconnect, and memories feel effortless.

The Cottage at Jones Road Ranch

Enjoy the solitude and beauty of a stay at the Cottage at Jones Road Ranch overlooking grazing horses. Next door is the Golden Oaks Micro Cellar winery. Tell them you're staying at the cottage and enjoy 15% off of wine tasting. Relax on the front or back porch with a views of the ranch or if you prefer a more active stay, hike or bike in the local Sam Houston National Forest or Huntsville State Park. Enjoy the fenced 1/2 acre dog play area. First 2 pets no charge , 3rd pet $25 fee.

Lake Conroe Cottage with Lakeview

1,000 sq ft. Cottage overlooking Lake Conroe located at Waters Edge resort, offering lake access, boat launch and docks. 800 sq.ft. deck includes a giant water cooled fan, fire pit with seating for twelve, outside dinning table that seats six and gas grill for outdoor cooking. Inside, sixteen feet tall ceilings create a large open main room with an overlooking loft; complete kitchen and wetbar with extra ice machine and wine cooler. Perfect for fishing trips & family parties!

1930s Home, King bed, sleeps 8, walk to Main St

“The Urban Oak” is a unique 1930’s home with Mid Century Modern Texas Styling. Located walking distance from the trendy yet established community of old town Tomball where you can shop antiques, boutiques, experience the rich food culture and take a stroll through the weekend farmers market! Hosted with Texas southern hospitality, 4 smart TVs & themed rooms with lux bedding, you are sure to enjoy your stay!

2300 Sq Ft, 4/2 - 2 Minutes From Lake Conroe

Perfect for friends and family! A spacious home in Walden on Lake Conroe in a quiet cul-de-sac. You have access to the Walden Marina (boat rentals), Walden Yacht Club (resort style pool with poolside bar & grill), 2 boat ramps, fishing, biking/walking trails, parks and more! For those that love to golf, enjoy Houston’s number 1 golf course! Margaritaville is only a 5 minute drive away.

Woodlands Modern Cottage-Top Rated! 3BR/Fast Wifi

Why You’ll Love the Space Cozy 3BR cottage in a quiet, safe neighborhood Minutes to Woodlands hospitals, trails & Market Street Fast WiFi + dedicated workspace for remote work Fully stocked kitchen for extended stays Smart TVs & BBQ grill for relaxing nights Perfect for medical visits, families & business travelers