Holiday rentals in Shenandoah

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Top-rated holiday rentals in Shenandoah

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Top guest favourite
The exterior of a charming two-bedroom house is shown, featuring a light yellow facade with brick accents. A welcoming front porch includes a wooden bench, and colorful flower beds frame the path leading to the entrance, inviting guests into the home.
Home in Conroe
4.95 out of 5 average rating, 92 reviews

2 BR house near The Woodlands

Cute two bedroom house located in a quiet neighborhood four miles from The Woodlands center! It’s a great location for concerts, races, conferences, shopping, etc. There are two bedrooms with queen beds (3rd bedroom is locked) and a blow up mattress available. (The master closet is also locked). It is a great space, but please only rent if you can respect the rules- ABSOLUTELY no parties/get-togethers, smoking or pets. (I only open my calendar a little at a time, but I’m open to longer rentals).

Superhost
A spacious living area is highlighted by a high open ceiling and large windows allowing for natural light. A dark leather sofa and two accent chairs are positioned around a decorative rug. A media console holds a flat-screen TV, creating a comfortable lounge environment.
Farm stay in Conroe
4.88 out of 5 average rating, 244 reviews

Country Retreat close to The Woodlands w/Pool

Stay 5 Min from The Woodlands in this one-of-a-kind retreat next to the Jones State Forest. 1/2 mile to walking, biking, or horseback riding on forest trails. At night you’ll gaze at twinkling constellations poolside or relax in our massage chair or jetted garden tub. Attend an outdoor concert at the nearby Cynthia Woods Mitchell Pavilion, one of the top amphitheaters in America. We are 5 min from The Woodlands Medical Center, and 10 min from The Woodlands Mall where you can shop till you drop.

Superhost
Home in Conroe
5 out of 5 average rating, 3 reviews

The Evergreen - Saltwater Pool + Bungalow + WiFi

🌿 The Evergreen — blends modern luxury with warmth; creating a space designed for connection and relaxation. 22-foot high ceilings, curated interior design, and seamless indoor–outdoor living make the home feel peaceful and elevated. Safety fence around the pool offers comfort for families. The private bungalow boasts its own entrance, full bathroom, kitchenette, and quadruple queen bunk suite. And with the game room/garage, “The Evergreen” becomes a retreat made for an unforgettable stay.

Guest favourite
A tranquil evening view of a gently flowing waterway is highlighted by vibrant pink lights reflecting off the surface. Modern buildings and illuminated archways frame the scene, while a clear moon hangs in the sky, casting a soft glow over the surroundings.
Home in Conroe
4.9 out of 5 average rating, 432 reviews

WOW!❤️Hidden Gem in Woodlands!💎Boat/RV allowed⭐️

Come home to this enchanting retreat in The Woodlands and near Houston! Only minutes to great shopping, dining, and entertainment, yet tucked in a relaxing natural garden oasis! Boats and RV's are welcome! Chic spacious bedrooms all furnished with Memory Foam beds and new 50" 4K TV's in each! Less than 30min to IAH and Lake Conroe, and less than 1hr from Houston! Minutes to Waterway, Hughes Landing! Walk to beautiful nearby hike/bike trails through wildflower gardens and bird sanctuaries!

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, 156 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.

Top guest favourite
A view into a serene bedroom features a spacious bed, accented by a horse-themed artwork on the wall. A dark wooden dresser stands nearby, and soft gray curtains frame a window providing ample natural light.
Guest house in Conroe
4.95 out of 5 average rating, 77 reviews

Hidden Gem! Medical Corridor! The Woodlands area!

Keep it simple at this peaceful and centrally-located place. 5 minutes from the Iconic Woodlands Market Place and the Woodlands Mall. Ideal for IRON MAN participants. Near 4 different Medical Centers and 1.5 miles from I-45. Within walking distance to HEB, Starbucks, Restaurants, and Stores. Traveling for business or fun, Casita has (1 queen size bed ) (and 1 twin mattress). Comfortable pillows and plenty of towels. Quiet place for ease sleep. Coffee Station and Microwave, hair dryer.

Top guest favourite
A modern entrance is framed by sleek black stone features and minimalistic lighting. A pathway leads to a glass door, flanked by two tall plants, while grass borders the walkway, providing a clear view of the home's contemporary design.
Home in Conroe
4.99 out of 5 average rating, 126 reviews

IvoryEdition NEW Luxury Estate Mins From Woodlands

This unique place has a style all its own. Modern, Open-Concept Luxury Estate. Entire Home top to bottom Glass Sliders. Minutes away from all of The Woodlands Texas beautiful attractions. The perfect place to come and enjoy a luxurious stay by yourself or with friends, there is plenty of bedrooms with their own bathroom! Work from home in our dedicated built in workspace with beautiful woodland views. Create your own mood with the entire home being powered by Philips HUE Lights.

Guest favourite
A two-story lakefront guesthouse is featured, showcasing expansive windows and a tiled roof. Lush greenery surrounds the property, and a patio area with outdoor seating is visible along the water's edge. The tranquil setting offers a serene view of the lake.
Guest house in The Woodlands
4.89 out of 5 average rating, 277 reviews

Lakefront Guesthouse: Pool, BBQ, Bike, Paddle Boat

Welcome to your lakefront escape - a spacious (~900 sq ft) private guesthouse suite with gorgeous Lake Paloma views, infinity pool access, and all the comfort you need for an easy, memorable stay. Perfect for families or small groups - up to 4 adults (or 5 guests including kids). NOTE: The guesthouse is attached to our home, where we live. Guests have a private entrance and private guesthouse space (not shared). The only shared areas are the driveway and backyard

Top guest favourite
An open living space combines a cozy sleeping area with a spacious bed covered in light bedding. A colorful light fixture hangs from the ceiling, illuminating decorative accents along the walls. A dining area and kitchenette are visible in the background, complemented by a small seating area.
Tiny home in Conroe
4.95 out of 5 average rating, 178 reviews

Cozy tiny house on small lake "The Maryhannah"

Relax and enjoy the calm serene of a country vibe feel in the middle of the city! This cozy tiny house feels like a gentle hug. Float around the seasonal splash pool, soak in the hot tub, enjoy a small container fire, or sit by the lake and watch the fish. Bring your fishing pole for catch and release stocked pond in this small vintage fishing community. Unit is on the back of the main house. Main house has area on the other side that you can’t see.

Guest favourite
A queen-sized bed is centered in the room, dressed with light blue bedding and complemented by beige pillows. Above the bed, an abstract wall art piece adds a splash of color. A bedside lamp provides soft lighting, enhancing the cozy atmosphere.
Home in Conroe
4.94 out of 5 average rating, 51 reviews

Cozy Studio Apartment The Woodlands

Cozy Studio Apartment with a Queen size bed for 2, private entrance, bathroom and kitchen. Perfectly situated between major towns around Houston, like The Woodlands. Located in a quiet neighborhood, less than 6 minutes from the Methodist, St. Luke's and Texas Children's Hospitals in The Woodlands, Texas. Just 9 minutes away from The Woodlands Mall, and 40 minutes from Houston Downtown. Located close to restaurants.

Guest favourite
A cozy sleeping area features a spacious bed, dressed with soft neutral bedding and decorative pillows. Natural light enters through multiple windows, with light curtains framing the view. The wooden accents and flooring add warmth to the overall atmosphere of the space.
Campervan/Motorhome in Conroe
4.89 out of 5 average rating, 149 reviews

The Hangout Spot

Recharge your soul in our cozy renovated Airstream! Whether you are traveling for work, visiting friends or trying to take a break from the chaos of life this is the perfect glamping experience. Enjoy a spacious layout that includes a queen sized bed, kitchenette with all the basics should you decide to cook a meal, nice dining area that could also double as a workspace, and comfortable shower.

Top guest favourite
A well-appointed bedroom features a queen size bed with a decorative headboard. Two elegant lamps frame the bed, illuminating striped accent pillows. Soft curtains drape over a window, allowing natural light to enhance the tranquil atmosphere, while an art piece complements the decor.
Guest suite in Conroe
4.97 out of 5 average rating, 31 reviews

Quiet & Gated, 2 BD- 1 BA, First Floor, 4 Guests

This conveniently located private suite in a large house is on the first floor with a private entrance, perfect for up to four guests and two cars. The location of this house is unbeatable. We are right off I-45 and 242. The house is in a gated community with walking trails, five minutes from Lone Star College, HEB, Costco, Walmart, Sam's Club, Mall, Med Centers. You'll love it here!

Popular amenities for Shenandoah holiday rentals

  1. Airbnb
  2. United States
  3. Texas
  4. Montgomery County
  5. Shenandoah