Top Vacation Homes in Montgomery County in 2026

A river with modern buildings and a bridge in the background.

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Top Cities in Montgomery County

A calm lake surrounded by dense forest and a clear sky.

Our top choices for Montgomery County vacation homes

A spacious living room with a large window overlooking a body of water, a dining area with a table and chairs, and a cozy seating area with patterned cushions.

1. Amazing waterfront 3-bedroom house with pool and hot tub on Lake Conroe

Montgomery

Elizabeth S.

A pathway leading to a staircase with a view of a grassy area and a body of water in the background.

2. Clemens' Cottage - Lakefront Bungalow on Lake Conroe w/ Private Dock & Boat Slip

Walden on Lake Conroe

Deyanira M.

A deck with a view of a lake, a pool, and a grassy area.

3. WATERFRONT HOME •PRIVATE POOL•BOAT DOCK•GOOD FISHING •GOLF •MEMORIES

Walden on Lake Conroe

JEFF C.

A spacious living room with a large sectional sofa, a coffee table, and a stone archway.

4. Waterfront home, 6 bedrooms private pool and dock on Lake Conroe

Montgomery

teresa e.

A modern kitchen with white cabinets, stainless steel appliances, and a patterned backsplash.

5. The Gathering Lovely Spacious 5-bedroom House

Magnolia

raul i.

A spacious living room with a large sectional sofa, a fireplace, and a view of the outdoors.

6. Catch, Paddle, Splash—Luxury 4BR on Lake Conroe

Willis

Tiffany G.

A modern outdoor living area with a 'WELCOME' sign, a hot tub, and a patio with seating.

7. HOT TUB! Private Tiny Home with one feature you won't find anywhere else...

Rayford

Treasia L.

AED 763 total

includes taxes & fees

21 Oct - 22 Oct

A modern living room with a wooden bench, a grey sofa, and a large potted plant.

8. Cozy 4-bedroom house in The Woodlands TX. Check it out for yourself!

Grogan's Mill

Marie T.

AED 1,469 total

includes taxes & fees

14 Oct - 15 Oct

A covered patio with a view of a lake, outdoor furniture, and a sign with rules.

9. Lake it easy, Fish, Kayak, Yard, Boat, Sleeps 20

Walden on Lake Conroe

Kiki T.

A modern kitchen with a large island, dining area, and a living room with a fireplace.

10. Pool/Jacuzzi Fun + Gameroom + Community Amenities

Walden on Lake Conroe

Leigh P.

A wooden deck with outdoor furniture, a covered seating area, and a view of a body of water and buildings in the background.

11. Beautiful Montgomery Home w/ Lakefront Deck!

Walden on Lake Conroe

Kaleigh M.

A laundry room with two front-loading washing machines, a dryer, and a refrigerator.

12. Lakefront Retreat by The Woodlands with Dock

Conroe

AED 1,774 total

includes taxes & fees

14 Oct - 15 Oct

A spacious living room with a fireplace, a ceiling fan, and a kitchen in the background.

13. Quiet 3BR Near The Woodlands | King Suite + Bonus Room | Family Friendly | Longer Stays Welcome

College Park

Jen K.

A modern kitchen with white cabinetry, a stainless steel refrigerator, a marble countertop, and three leather bar stools.

14. Lone Star - Elevated Lakeside Retreat

April Sound

James G.

A spacious kitchen with white cabinetry, a central island, stainless steel appliances, and a view to the dining area.

15. Best of The Woodlands

Alden Bridge

Hannah C.

A covered outdoor seating area with a view of a river and buildings.

16. Boat Parking 🚤 Quiet Canal ☀️ 4 Bed Townhouse by EverSan Cooper Getaways

Walden on Lake Conroe

Caden R.

AED 1,573 total

includes taxes & fees

2 Nov - 3 Nov

A spacious living area with a sofa, dining table, and chairs, a kitchen with modern appliances, and large sliding glass doors leading to an outdoor patio.

17. Lux Lakefront with Game-room, Community Pool, Paddleboards, and more!

Willis

Susan B.

A dining area with a round table, black chairs, and a cabinet with glass doors.

18. Spacious Lake Conroe Lakeview Home, 3 BR/ 3 BA, Gated Community, Sleeps 6-8

April Sound

"The stay was quiet, in a gated community, and the place is clean. We did find a cockroach, but that's normal for summer in the south. The one issue we ran into was the guest policy. If you want friends/family in the area to stop by to say hello, make sure they are on the listed names in the reservation beforehand. We stayed for a wedding and asked if the groom's two brothers and a friend could join the five of us after the rehearsal dinner for board games, but we were declined. The is the first...

Andrew G.

A spacious dining area with wooden paneling, a large window, and a modern kitchen in the background.

19. Escape by the lake 💕

April Sound

"Me and my family loved staying at “escape by the lake “(April Sound) it’s comfortable, spacious, awesome view from the balcony, large beds, they provide mostly everything that you need . We have no complaints at all because we enjoyed our stay at this place host was quick to respond to any and all questions and very nice and understanding. Rooms were clean, living room and kitchen as well. Me and my family will surely stay at this place if available for whenever we come back to Conroe."

Pablo E.