Holiday houses in Montgomery County

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Top-rated holiday rentals in Montgomery County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A private pool is visible with a gently sloping lounge chair floating on the water's surface. Surrounding palm trees and natural stone formations create a serene ambiance under bright blue skies.
Holiday home in Montgomery
4.95 out of 5 average rating, 193 reviews

Prancing Horse Estates:10 acre resort w/pool, spa

Welcome to Prancing Horse Estates! This is a private gated 10 acre estate with private pool, spa and waterfall + 4 bedroom home. You’ll love it if you like upscale indoor style combined with beautiful outdoor space. 10 acres- 4 meadow and 6 densely wooded with 2 paths along the creek, with lovely poolside space with seating for 16+. Well stocked library, children’s room, indoor/outdoor games. Certified Wildlife Habitat® site with the National Wildlife Federation and Texas Conservation Alliance.

Guest favourite
A rooftop space showcases a 75-inch television mounted on a gray wall. Two modern wicker chairs with blue cushions flank a circular wooden coffee table, which is adorned with a variety of magazines. Green foliage is present, adding a refreshing touch to the area.
Home in Conroe
4.95 out of 5 average rating, 155 reviews

Contemporary 3 Bedroom-Rooftop- Home

Kick back and relax in this new construction, modern, stylish home. Located in the heart of downtown Conroe. Extremely close to great dining, entertainment, and the Conroe convention center. About 15 minutes from Lake Conroe, this vacation will be one to remember! Enjoy a movie on the rooftop under the stars or make memories around the outdoor fire pit in the backyard. Get cozy in front of the 75” television. With televisions in every room, enjoy a peaceful night’s rest on comfortable beds.

Top Guest favourite
Townhouse in Montgomery
4.96 out of 5 average rating, 159 reviews

Lakefront Retreat | Swim, Fish & Paddleboard

Escape to EverGreen Cove, a pet-friendly 🐾4BR/3BA lakeside townhouse on Lake Conroe. Wake up to calm cove views, spend the day paddle boarding and swimming off the bulkhead, then grill dinner while the sun sets over the lake. 🌅 ☀️Paddle boards included 🏊🏼Swim directly from the property 🎣Fish from the bulkhead 🚤Bring your boat and tie up on our bulkhead 🤿Pool access 🍔Grill and outdoor dining (bring your own charcoal) 🌅Sunset on the deck ⚓️Nearby boat rentals and lakeside restaurants

Guest favourite
A functional garage with a white door is complemented by a covered gazebo, creating a shaded outdoor area. The structure is surrounded by lush green trees and a well-maintained yard, offering a peaceful setting for relaxation.
Cottage in Montgomery
4.96 out of 5 average rating, 102 reviews

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.

Luxe
Treehouse in Montgomery
4.98 out of 5 average rating, 175 reviews

Unique Lux Treehouse: Lakefront, Gameroom, Kayaks

Escape w/ the family to "Iron Pine Treehouse" next to Lake Conroe on a small private lake. Enjoy lake views from nearly every room w/ luxury finishes. Trees intersect the deck--a canopy of leaves overhead for a treehouse effect! 13 beds, sleeps 17 comfortably: 1 King, 2 Queens, 9 Twin bunks, 1 queen sofa bed Kayaks/Paddleboards and a game-room. There's even a connected studio with a full kitchen! Fish off the private dock | Only 3 minutes to Lake Conroe public boat ramp or boat rentals!

Top Guest favourite
Home in Montgomery
5 out of 5 average rating, 13 reviews

Little Cottage in the Forest

Come experience quiet luxury in a quaint cottage nestled amidst the forest. This little 5-star charmer is the perfect romantic getaway for couples seeking a respite from a busy life. Highlights • Private 3-acre property in Sam Houston National Forest • Outdoor soaking tub under the pine trees • Large patio with fire pit, grill, and lounging area • 10 minute drive to Lake Conroe boat ramp. • 10 minute drive to Lone Star Hiking. • Peaceful, nature-immersed setting with modern comforts

Top Guest favourite
Home in Montgomery
5 out of 5 average rating, 19 reviews

Mini-goats, Covered Deck at Conroe Casita

Welcome to this thoughtfully designed bohemian farmhouse, home to our adorable mini-goats — Pookie and Cowboy. This charming, pet-friendly retreat in Lake Conroe/Montgomery offers the perfect private getaway for you and your family, while still being conveniently located within an hour from downtown Houston. You’ll be just: • 8 minutes from Lake Conroe Park • 15 minutes from the historic Old Montgomery • 30 minutes from The Woodlands Relax, unwind, and enjoy the country charm

Top Guest favourite
The living area is characterized by a comfortable sofa positioned near a coffee table and a smart TV. A dining table with four chairs is set for meals. Natural light enters through large glass doors leading to a balcony, while decorative touches enhance the space.
Condo in Montgomery
4.98 out of 5 average rating, 53 reviews

Oasis on the green!

Come enjoy a family getaway, a weekend to play the course, or an escape to enjoy the area food, wineries, and shopping. This 2-bed 2-bath condo is located on the Walden Golf Club Course, across the street from the driving range. The condo has a fully equipped kitchen, a dining area with a coffee bar, and a cozy living room. The main bedroom has a queen size bed and a private bathroom with a walk-in shower. The second room has two full size beds with access to the hall bathroom.

Top Guest favourite
Home in Magnolia
4.97 out of 5 average rating, 73 reviews

Ranch house in Magnolia, TX aka The Zaiontz Ranch

Escape to our serene lakeside ranch house. Our Airbnb has 3 bedrooms, 2 bathrooms, fully-equipped kitchen, living room, dining room, and formal living room. Step outside to be greeted by the tranquil lake view and the pastoral beauty of grazing cattle. 14 miles to Texas Renaissance Festival, 20 minutes to Lake Conroe, 15 minutes to shopping, groceries, pharmacies, restaurants. 2 miles from Meeker Mark wedding venue. Note: The 2nd floor is not part of the rental.

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, 533 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.

Guest favourite
A shaded balcony offers a view of the waterfront, featuring a table and chairs arranged for outdoor relaxation. Lush trees provide natural greenery, while the lake stretches out beyond well-maintained lawns and adjacent patio areas.
Condo in Montgomery
4.95 out of 5 average rating, 159 reviews

Lakefront | Pet Friendly | Paddleboard Incl | Pool

Welcome to Alluring Lakefront Condo — a stylishly furnished 2-bedroom, 2-bath retreat with direct lake views and a relaxing, resort-style feel. Whether you’re here for a weekend getaway, fishing trip, wedding, or extended escape, you’ll find everything you need for a comfortable and memorable stay — including a Complimentary Self-INFLATABLE PADDLEBOARD for you to enjoy on the lake. Just steps from the water and minutes from dining, shopping, and outdoor adventure.

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
4.92 out of 5 average rating, 166 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.

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