Holiday rentals in Montgomery County

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Top-rated holiday rentals in Montgomery County

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Top guest favourite
A cozy outdoor space is depicted, featuring four orange adirondack chairs arranged around a circular fire pit. A gazebo stands in the background on a wooden deck, surrounded by potted plants. A path of stone tiles leads through the gravel yard, creating a welcoming atmosphere.
Home in Tomball
5 out of 5 average rating, 105 reviews

Tomball House - Steps to Coffee, BBQ, Tex-Mex

Spacious 2/2 in Tomball’s historic Old Town, steps away from restaurants, shopping, antiques, and weekly farmer’s market. This one has it all—near everything yet tucked away on a peaceful street. ✔️ 2 minute walk to Honor Society Coffee, Graze Restaurant, Tejas Chocolate+Barbecue, Callie’s Kitchen ✔️ 5 min walk to Cisco’s (Baja/Tex-Mex), Tejas Burger Joint (smoked burgers), Thirsty Bee Meadery, Cherry Street Antiques, Whistle Stop Tea Room ✔️ 3 minute drive to Boxwood Manor & Ella's Garden

Guest favourite
Home in Montgomery
5 out of 5 average rating, 10 reviews

The Lynbrook- Home Near the Lake

Come getaway to our Mini Modern retreat in Lake Conroe Village! This quaint home is tucked away off the highway & a 5 minute drive to Lake Conroe marinas, restaurants, groceries, activities & more! 20 mins to Bernhardt Winery, 25 mins to TX Ren Fest, 10 mins to Margaritaville & 35 mins to downtown Houston/IAH airport! Ask about our complimentary KEY CARD to the esteemed Walden neighborhood-only 10 mins away. This home may be mini, but it is mighty FULL of extra touches and luxury comfort!

Guest favourite
A red, barn-style tiny house is seen on a wooden deck, accented by potted plants. A single chair is positioned on the deck, with a small side railing visible. The entrance features a door with a window above it and decorative shutters on either side.
Tiny home in Montgomery
4.89 out of 5 average rating, 61 reviews

Peaceful Cozy Cottage

Cute “not so tiny" tiny house that is light, bright and especially clean. This cozy cottage is 75 feet away from the main house on our 6 acres of trees with a seasonal creek, birds, squirrels and deer. Nestled against the trees and backing the creek, enjoy the deck with your morning coffee or star gazing at night. Our country paradise is 10 minutes from city conveniences with plenty of restaurants and movie theaters. Enjoy Old Town Montgomery and The Woodlands, both just 15 minutes away.

Top guest favourite
A kitchenette is displayed, featuring a sleek countertop with a stainless steel sink. An electric countertop oven sits alongside a coffee maker, complimented by a shelf holding dishware and decorative items. A roll of paper towels and dish soap are positioned for easy access.
Guest house in Shenandoah
5 out of 5 average rating, 158 reviews

The Woodlands/Shenadoah Casita

Right in the heart of all of the action, you will find this super cute, well appointed Casita with queen bed. You will have your own space and everything you need for your getaway. We provide off street parking, outside patio, hot tub and access to the grill. This casita is located across the patio from our primary residence. While you do have your own space you may bump into us outside feeding the chickens or letting our little Yorkie out to potty. You’ll access through the side gate.

Guest favourite
The image collage showcases various aspects of The Carlton Family Lake House, including a cozy bedroom with stylish decor and a serene view of the lake from the living area. Natural light floods the space, enhancing the calm atmosphere, while outdoor scenes capture the tranquility of the lakeside setting.
Home in Montgomery
4.94 out of 5 average rating, 215 reviews

Serenity on the Lake

Forget your worries at The Carlton Family Lake House. It’s truly serenity on the lake…the calmness and peaceful you’ll feel here. This property on Lake Conroe in April Sound gated community is dedicated to ensuring a peaceful, comfortable & rejuvenating experience. The spacious 1,824 sq ft condo is perfect for a group of friends & family of 6 comfortably. Located conveniently near wedding venues, breweries, Margaritaville & many restaurants. Come & relax on your lake front property.

Guest favourite
A cozy living room features a leather sofa paired with a comfortable armchair. A coffee table is adorned with vibrant decor, while a patterned area rug adds warmth. Soft lighting is provided by blue lamps on side tables, and a colorful artwork of trees decorates the wall.
Apartment in Montgomery
4.97 out of 5 average rating, 147 reviews

Rental Retreat TX-Come Relax on Lake Conroe!

Experience beautiful sunsets on the lake!! 1st floor w/all amenities, 1 bedroom (queen), & living room w/sleeper sofa (queen). Quick access to pool & lake. Kitchen cooking utensils, dishes, range, refrigerator, microwave & dishwasher. Shower & tub, washer & dryer. Access to fitness & racquet club, yacht club & grill, and private boat launch. Parking close to the door. Fishing, golfing, boating, tennis, swimming, walking trails and close proximity to Sam Houston National Forest.

Top guest favourite
A modern cabin is set within a forested area, featuring a welcoming front porch with steps leading up and outdoor seating. Large windows are present, allowing natural light to fill the interior. A well-maintained grassy yard surrounds the cabin, enhancing the serene environment.
Cabin in Montgomery
4.97 out of 5 average rating, 141 reviews

Cabin In The Forest - Houston National Forest

Kick back and relax in this calm, stylish cabin in the forest. It's only walking distance to the beautiful Lone Star Trail in Sam Houston National Forest. This forest cabin has access to a fishing pier that is fully stocked with native fish (no license required); please follow lake rules. Bring your kayaks and paddleboards to enjoy the lake. There's lots of scenery (forests, wildlife, lakes, countryside, etc.); you never know what you can capture, so bring your camera!

Top guest favourite
A serene scene features a wooden dock extending over calm lake waters, with a dog standing nearby. The sunrise casts a warm glow over the landscape, while mist rises gently from the surface of the lake, creating a peaceful atmosphere.
Home in Montgomery
4.94 out of 5 average rating, 492 reviews

The Quick Getaway: Entire house on private lake!

Need to escape? We've done the work! INCLUDED: Breakfast - eggs, bagels, coffee, filtered water, creamers, sugar & a selection of teas. Location is secluded, not remote! Got a boat? Bring it! Boat access inc. @ neighborhood ramp. 1100 SF lakefront house in Montgomery, TX. Max 4 PPL - 2 Bdrms: 2 queen beds, 2 bathrooms, 2 porches, charcoal grill & paddle boat! * FIDO friendly <30lbs, $25 fee - per pet ESA pets the same. We love all pets, got a big dog? Ask us.

Top guest favourite
A welcoming living area is arranged with a mix of seating, including two armchairs and a sofa. A coffee table sits in the center, and a mantel with a fireplace provides a focal point. A flat-screen TV is mounted above, and light floods the space through French doors.
Townhouse in Montgomery
5 out of 5 average rating, 44 reviews

The Pink Magnolia-walk to lake/playground/dog park

Time to relax in this newly renovated 2-bedroom, 1.5-bath townhome, located within walking distance of Lake Conroe! With new finishes from top to bottom, the Pink Magnolia offers a comforting interior, fully-fenced backyard oasis, and an ideal location. A playground, dog park, and marina are within a short walk. Guests will also be able to enjoy all Walden amenities - resort-style pool, fitness center, tennis courts, hike and bike trails, boat access, and more!

Guest favourite
A cozy sleeping area showcases a queen-sized bed draped with a soft throw, accented by a patterned coverlet. Nearby, a warm-toned wooden dresser is positioned beside the bed. Red and black curtains frame the window, enhancing the rustic interior highlighted by wooden beams.
Barn in Montgomery
4.94 out of 5 average rating, 137 reviews

Valhalla!

This memorable place is anything but ordinary. A Viking-inspired getaway complete with porch, shower, bathroom, kitchen and a full-functioning sauna! This mini-apartment is in the top section of a barn and you may have to duck your head. There is a queen-sized bed and an additional mattress for someone else if needed. Take a stroll in the woods or take a quick 5 minute drive to the lake! Now with upgraded Air Conditioning! Pets welcome, $$Fee.

Top guest favourite
Flat in Montgomery
5 out of 5 average rating, 19 reviews

Walkable Studio Retreat

Family-friendly studio in the heart of the neighborhood! Walk to restaurants, coffee shops, groceries, boutiques, parks, playgrounds, and trails right outside your door. Cozy, modern, and fully appointed for short or long-term stays, this space is ideal for couples, business travelers, grandparents, or families visiting nearby. Enjoy comfort, convenience, and unbeatable walkability—perfect for your next stay.

Guest favourite
A cozy studio space features a spacious bed with crisp linens, complemented by soft lighting. A decorative wall art piece is visible, alongside a sliding glass door leading to a closet. The room includes a small dining table and chairs, enhancing functionality.
Flat in Spring
4.96 out of 5 average rating, 207 reviews

The Woodlands Studio

Take it easy at this unique and tranquil getaway. 5 minutes from downtown The Woodlands where you can find all the atractions, parks and next to all the trails what the area can offer. Only 20 miles from Houston airoport . This little studio can be a place for a short time or longer.

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