Vacation rentals in Shenandoah

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Top-rated vacation rentals in Shenandoah

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

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Top guest favorite

Home in Conroe

Clean & Cozy new Home, 30 mins to George Bush INTL

Brand New Home! In quiet neighborhood! High speed Internet! work station! few minutes to I-45 & Grand Parkway, 30 mins to Downtown & IAH,The Woodlands Mall, dining & entertaining places, like- Cynthia Woods Mitchell Pavilion, Six Flags Hurricane Harbor, &The Woodlands Market Street and Marriott Center. close by is Walmart, HEB, Target,Sam's , Costco. Very close to Lake Woodlands & Lake Conroe. Enjoy the early AM or evening walk at the Woodland Waterway. Free complimentary coffee/tea/water/snacks

4.98 out of 5 average rating, 129 reviews

Top guest favorite

Home in Shenandoah

Sassafras Manor: Anti-Corporate Stay: City Oasis!

Welcome to your ultimate creative sanctuary. Now the newly available Main House at Sassafras Manor!" Nestled in historic Lakeland (77384)—a hidden 1960s neighborhood originally built as a fish farm—Sassafras Manor is a 64-year-old artist's cabin that feels like a year round vacation! It’s beautifully imperfect, bursting with color, and intentionally designed for deep relaxation. Longer stay rates negotiable." The tiny house “Maryhannah” is available for an extra fee if you want to include it!

4.95 out of 5 average rating, 198 reviews

Guest favorite

A spacious living area features high, vaulted ceilings with exposed wooden beams. A large, L-shaped sofa, accented with yellow pillows, provides ample seating. A wall-mounted television is positioned above the fireplace, complemented by a neatly arranged shelf nearby. Natural light enters through sheer curtains.

Home in Shenandoah

Shenandoah / The Woodlands - Easy Freeway Access

Experience The Woodlands up close! Just minutes from entertainment, ideal for work, family, nurses, or vacationers. Complimentary Hulu and other streaming services available, plus fast, reliable internet—perfect for remote work Professionally cleaned, quiet, safe neighborhood. Hulu, fast Wi-Fi, washer/dryer included. Near hospitals, short walk to park, close to lakes. Book now for comfort, convenience, and peace of mind! Make yourself at home and experience The Woodlands at its best!

4.78 out of 5 average rating, 158 reviews

Superhost

A single-story brick house is featured surrounded by a well-maintained lawn. The front porch, framed by symmetrical green shutters, offers two seating areas. A clear path leads to the entrance, bordered by neatly trimmed shrubs, creating a welcoming appearance.

Home in Shenandoah

Spacious 4BR near Woodlands - Perfect for Groups!

You’ll love this centrally-located house close to the Woodlands in a safe, quiet neighborhood with easy access to I-45. Relax in the jacuzzi tub and enjoy the covered backyard patio w/ pet-ready fenced yard & fun play set for kids. 3 minute drive - Memorial Hermann, St.Luke’s, Texas Children’s Hospital & Portofino to shop and dine. 5 minute drive - The Woodlands Mall, Market Street, Waterway Square, The Pavilion, Hughes Landing, Restaurant Row and various wedding venues & sports complexes.

4.85 out of 5 average rating, 160 reviews

Top guest favorite

A bright living area features a ceiling fan and large windows allowing natural light. A decorative rug adds warmth to the wooden floor. A wall-mounted TV stands opposite a cozy fireplace, while a breakfast bar with stools is positioned near the open layout.

Home in The Woodlands

Spacious & Cozy 4BR Home in The Woodlands

• 2050 sq ft, 4BR home on a tree lined neighborhood • Well-appointed with 1 King, 1 Queen, 2 Full beds • Fully stocked and equipped kitchen with Kurig coffee available for each guest • 3 large screen smart TVs in three rooms • Located in the heart of The Woodlands in the Indian Springs sub-division “Very spacious and comfortable with a very well stocked kitchen!” Natalie “The furniture was super comfortable” Andrea “The neighborhood is great and has many areas for walking under trees” Andres

4.92 out of 5 average rating, 118 reviews

Top guest favorite

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

1 mile from everything!• Dining • Family Friendly

-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!

4.99 out of 5 average rating, 136 reviews

Top guest favorite

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.

Guesthouse in Shenandoah

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.

5.0 out of 5 average rating, 197 reviews

Top guest favorite

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.

Guesthouse in Conroe

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.

4.95 out of 5 average rating, 101 reviews

Guest favorite

The exterior of a single-story home is showcased, featuring a manicured lawn and lush landscaping. A light-colored garage door is visible, complemented by a brick façade. Large windows allow natural light to illuminate the front interior, framed by greenery from nearby trees.

Home in The Woodlands

Woodlands Retreat 3bdrm 2bath

Long term stays welcomed ! One story home perfect for families. This home is located in a quaint cul-de-sac half a mile to i45. You are only minutes away from all the hospitals and shopping centers. Whether you are in town visiting family, here for an event, or seeking treatment this house is perfect for you and your family, this includes your four legged family as well. All mattresses are 12” memory foam for your comfort. Lots of near by amenities like a pool, tennis and playground.

4.93 out of 5 average rating, 134 reviews

Top guest favorite

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

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.

4.99 out of 5 average rating, 154 reviews

Top guest favorite

A spacious green lawn is surrounded by tall trees, with dappled sunlight filtering through the leaves. The cabin's front porch features wooden railings and is set against the backdrop of a natural landscape, inviting relaxation in a serene environment.

Cabin in Magnolia

Woodlands Retreat - Looks Rustic, Feels New

This freshly renovated retreat in Magnolia is the perfect relaxing getaway. Enjoy the peace and quiet of a 5-acre natural wonderland. Minutes away from world-class shopping, dining, and recreation in The Woodlands, TX. The home features 4 furnished bedrooms, a fully furnished kitchen and dining area, a spacious living room with pull-out sofa, 2 full baths, high-end linens, a stocked laundry room, and plenty of outdoor space to enjoy. We hope to see you soon!

4.99 out of 5 average rating, 239 reviews

Guest favorite

Home in Spring

Woodlands 4BR | 11 Guests Near Pavilion & Waterway

🏡 Your Woodlands home base! Spacious 4BR sleeps 11, minutes from Cynthia Woods Mitchell Pavilion (Top 5 amphitheater worldwide!), The Woodlands Waterway, Market Street luxury shopping. ☕ Fast WiFi • Full Kitchen • Free Parking • Self Check-In 🎵 Pavilion — same zip! | 🏬 Mall — 10 min | ✈️ IAH — 22 min | 🏙️ Downtown Houston — 29 min Perfect for: concert-goers, business travelers, medical travelers, families, large groups, extended stays!

4.94 out of 5 average rating, 137 reviews