Montgomery Cottages - Vacation Rentals in Windwood

Dog-friendly Cypress Vacation Rental w/Lanai! From US $502
         

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New
Cottage
  • Air Conditioner
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  • Pet Friendly
2-bed/1 Bath Amazing & Private Guesthouse in Cypress with Pool From US $142
         

Luxury Places to Stay in Windwood

Over 183+ Luxury Places to Stay in or Near Windwood
♕Fancy Home near Cypress♕ From US $1,822
         

10.0 (1 Review)
House
  • Air Conditioner
  • TV
  • Security/Safety
Family-Friendly 6BR Retreat w/Pool in Houston From US $680
         

9.0 (37 Reviews)
House
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  • Pet Friendly
2King Suites, HeatedPool, Arcade & Pickleball From US $673
         

9.0 (4 Reviews)
House
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  • Pet Friendly
Corporate I Free Parking I Properties By Preston From US $588
         

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Houston Social Court & Event, Pickleball, Billiard From US $571
         

Modern Spacious Heated Pool & Hot Tub Paradise Home. From US $549
         

9.8 (7 Reviews)
House
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  • Pet Friendly
C Creek 4316 I New Construction 2Bd Apt I Gated From US $541
         

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New
Apartment
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Pool Paradise Game Tables Sleeps 16 Grill From US $522
         

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7.0 (2 Reviews)
House
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  • Pool

Top-Rated Vacation Rentals with a Pool in Windwood

Over 56+ Top-Rated Vacation Rentals with a Pool in or Near Windwood
Home with pool! Enjoy savings of 20-30 percent off today! From US $391
         

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10.0 (1 Review)
House
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  • Pet Friendly
Modern 4BR Retreat Family & Pet Friendly Near Cypress, Tomball, Spring From US $198
         

Hyatt Place Houston NW Vintage Park From US $113
         

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9.2 (1004 Reviews)
Hotel
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Element Houston Vintage Park From US $145
         

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8.8 (1001 Reviews)
Hotel
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Courtyard by Marriott Houston Northwest From US $125
         

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8.8 (732 Reviews)
Hotel
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SpringHill Suites by Marriott Houston Northwest From US $123
         

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8.8 (728 Reviews)
Hotel
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Holiday Inn & Suites Houston NW - Willowbrook by IHG From US $97
         

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8.8 (454 Reviews)
Hotel
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  • Pool

Pet-Friendly Vacation Rentals in Windwood

Over 67+ Pet-Friendly Vacation Rentals in or Near Windwood
New Construction 2bd Apt I Properties By Preston From US $494
         

Red Roof Inn Houston - Willowbrook From US $70
         

8.8 (664 Reviews)
Hotel
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  • Pet Friendly
Cozy Spacious Family Pets Woodsy Gazebo with game room office From US $315
         

10.0 (26 Reviews)
House
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  • Parking
  • Pet Friendly
Golf & Get Outside - Family Home in Houston! From US $253
         

10.0 (3 Reviews)
House
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  • Parking
  • Pet Friendly
Family Retreat: Patio, RokuTV, Sleeps 10 From US $322
         

10.0 (2 Reviews)
House
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  • Parking
  • Pet Friendly
Dog-Friendly Cypress Vacation Rental w/Lanai! From US $303
         

10.0 (2 Reviews)
House
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  • Parking
  • Pet Friendly
Luxurious Home Retreat with stylish design From US $185
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
See More Pet-Friendly Vacation Rentals in Windwood on PetFriendly.io

Large Vacation Homes & Villas in Windwood

Over 15+ Large Vacation Homes & Villas in or Near Windwood
Quiet & Relax Getaway- Pool Table, Grill, &Netflixnn From US $334
         

10.0 (3 Reviews)
House
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  • TV
Spacious 4-bedroom house with AC, WiFi in peaceful Cypress From US $484
         

9.4 (6 Reviews)
House
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  • Parking
  • Pet Friendly
Welcome 4 Bedroom house North Houston! From US $218
         

7.0 (2 Reviews)
House
  • Air Conditioner
  • Designated Smoking Area
  • TV
Pool Paradise Game tables Sleeps 16 Grill From US $100
         

3.8 (4 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool

Wheelchair Accessible Vacation Homes in Windwood

Over 26+ Wheelchair Accessible Vacation Homes in or Near Windwood
Fully Furnished Pool View Apartment in Tomball, TX From US $169
         

8.0 (6 Reviews)
Apartment
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  • Pet Friendly
  • TV
1 Bedroom w Patio, Workspace, Gym, and Pool From US $92
         

New
Apartment
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Palace Inn Blue Jones Rd From US $87
         

9.2 (108 Reviews)
Hotel
  • Parking
  • Designated Smoking Area
  • Wheelchair Accessible
Luxurious Apartment Living in Tomball, TX From US $171
         

7.4 (6 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Modern Suite | Free Breakfast + Free Wi-Fi From US $124
         

10.0 (1 Review)
Condo
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2 Bedroom | Free Breakfast + Outdoor Pool From US $234
         

8.0 (1 Review)
Condo
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  • Parking
  • Pool

Windwood Vacation Rentals and Airbnb Places to Stay Under $200

Over 108+ Windwood Vacation Rentals and Airbnb Places to Stay Under $200
Lovely home - Workspaces - King Bed - Fast WiFi From US $147
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Posh royalty living in a gated new neighborhood! From US $194
         

Palace Inn Blue Tomball Parkway From US $71
         

9.2 (551 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
A wonderful Yoga Retreat Mini House in Houston surrounded by Nature. From US $168
         

Posh living in gated new area! From US $180
         

8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
C Creek 4316 I New Construction 2Bd Apt I Gated From US $121
         

8.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Furnished Pool View Resort From US $169
         

5.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 1Bd Apt I Properties by Preston From US $69
         

2.0 (1 Review)
Apartment
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  • Pet Friendly

Instantly Bookable Vacation Homes in Windwood

Over 52+ Instantly Bookable Vacation Homes in or Near Windwood
Cypress 4316 I New Construction 2Bd Apt I Gated From US $113
         

Cozy home in gated neighborhood! From US $204
         

8.8 (3 Reviews)
House
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  • Parking
  • Pet Friendly
3-bedroom vacation home 13 minutes from Willowbrook Mall From US $372
         

Spacious 4-bedroom house with AC in friendly Houston neighborhood From US $251
         

About Windwood Vacation Rentals

With more than 3 Windwood vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windwood.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Windwood, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windwood. Places to stay near Windwood with prices averaging $251 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Windwood with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windwood

Type Count
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Windwood

Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windwood.

Weather in Windwood

View the weather forecast for Windwood before booking your Windwood Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Windwood Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Windwood?

Currently, the total number of properties listed in 2026 is over 3 in the Windwood area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windwood.