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Holiday rentals in Shenandoah

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Top-rated holiday rentals in Shenandoah

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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, 237 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.

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, 91 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)

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, 430 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 comfortable living area features a blue sofa and two patterned chairs, positioned around a wooden coffee table. Natural light filters in from the window, complementing the soft grey walls and light-colored flooring. A mounted TV and clock add functional elements to the space.
Home in Shenandoah
4.99 out of 5 average rating, 78 reviews

Cozy Shenandoah Home < 2 Mi to The Woodlands Mall!

This charming vacation rental in Shenandoah is the perfect home base for couples and small groups looking for a comfortable spot to kick back between adventures! The 2-bedroom, 1-bathroom home is in a great location, so venture out to attend local concerts, shop at The Woodlands Mall, and stroll through the neighborhood. Plus, the home is near multiple hospitals and medical centers — ideal for traveling healthcare professionals. Other perks include off-street parking, a Smart TV, and WiFi.

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, 151 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
The exterior of a modern home is shown, featuring a stone-accented facade. A neatly landscaped lawn is visible, complemented by a curved driveway leading to two wooden garage doors. Lush greenery lines the path to the entrance, creating a welcoming approach.
Home in The Woodlands
4.99 out of 5 average rating, 108 reviews

Best location in Woodlands! 1 mile from everything

-Best location in The Woodlands! 3 bedroom peaceful home, walking distance from Hughes Landing. 1 mile from Woodlands Mall, Market St, Waterway, hospitals, & Whole Foods. -Access to tree lined walking/biking trails next to house. -3 bedrooms, 2.5 bathrooms, 2 living rooms. Small private backyard w/patio furniture. -Family friendly home; I provide pack n play, highchair, toys, dishes, & some baby proofing. -Desk & remote working area -coffee/tea bar & ample kitchen supplies provided!

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, 74 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 light-filled studio space showcases a king-sized bed with a tray positioned on top. A cozy seating area includes a sofa, small dining table, and kitchenette, all complemented by a large window and skylight, bringing in natural light.
Guest house in Conroe
4.99 out of 5 average rating, 85 reviews

Resort-Style Studio on the Golf Course!

✨ A Serene Retreat with a Touch of Luxury ✨ Escape to this charming private studio, a hidden gem in a peaceful golf course community. Perfect for a romantic getaway, solo retreat, business trip, friend's trip or parent-kiddo escape, this stylish space offers thoughtful details, a deck overlooking the golf course, and resort-style comfort. 📍 Prime Location – Just minutes from The Woodlands and Conroe, enjoy nature’s tranquility with easy access to dining, shopping, and entertainment.

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
5 out of 5 average rating, 118 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
Home in Conroe
5 out of 5 average rating, 6 reviews

(4M) Charm Studio The Woodlands

Take a break and unwind at this peaceful Studio. Just 9 minutes away from The Woodlands Mall and 40 minutes from Houston Downtown! Quiet neighborhood, less than 6 minutes from The Methodist, St. Luke's and Texas Children's Hospitals in The Woodlands. This space is ideal for traveling healthcare professionals, a couple or single person. Within 5 minutes from Lone Star College, HEB, CVS, restaurants and other convenience stores. Enjoy the charms of Woodlands/Conroe surroundings!

Top guest favourite
A modern dining area features a round wooden table set for four, complete with plates, bowls, and utensils. Four black upholstered chairs surround the table. The space is illuminated by recessed lighting, with a decorative vase on the table and a large piece of wall art in the background.
Guest house in Conroe
5 out of 5 average rating, 23 reviews

A home away from home.

"Cozy and functional 1 bedroom apartment with king bed, kitchen, equipped, living room, private bathroom, dining room, laundry room. Located in an excellent area, a few minutes from mall and the Woodlands financial area, hospitals, restaurants, shops and only 20 minutes from Bush Airport, ideal for travelers and professionals. Enjoy a comfortable stay with all the services included. Your best choice for location and comfort. 20 minutes from Lake Conro. Totally independent.

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, 176 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.

Popular amenities for Shenandoah holiday rentals

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