Discover Your Perfect Westmorland Vacation Homes

Westmorland Luxury Rentals

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Westmorland Pet Friendly Vacation Rentals

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9.7 (13 Reviews)
Bed & Breakfast
Charred Oaks Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
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9.4 (58 Reviews)
House
Cecil's Cozy Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Westmorland Large Vacation Homes

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7.8 (24 Reviews)
Bed & Breakfast
Montgomery Inn BnB
  • Air Conditioner
  • Parking
  • TV
View Availability
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Why Choose Rent By Owner for your Westmorland Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Westmorland

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit ensures you can fully enjoy the charm and amenities of this destination, whether you're exploring during peak seasons or seeking a quieter retreat in the region.

Peak Season Highlights

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Spring (March to May)

During spring, the region experiences mild temperatures and vibrant scenery, making it an ideal time to explore local attractions and enjoy pleasant weather.

Average Temperature Daytime: 65°F - 75°F - Nighttime: 45°F - 55°F
autumn
Fall (September to November)

Autumn brings cooler temperatures and beautiful fall foliage, perfect for outdoor activities and enjoying the area's scenic views.

Average Temperature Daytime: 60°F - 70°F - Nighttime: 40°F - 50°F

Off-Season Highlights

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Summer (June to August)

In summer, the area can be hotter and more humid, which might be less ideal for outdoor pursuits, but it's also a lively time with many local events.

Average Temperature Daytime: 85°F - 90°F - Nighttime: 65°F - 70°F
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Winter (December to February)

Winter months often bring colder temperatures and occasional snowfall, creating a quieter atmosphere with fewer tourists and lower rates for vacation rentals.

Average Temperature Daytime: 40°F - 50°F - Nighttime: 25°F - 35°F

Weekly Weather Forecast for Westmorland

How to Book Your Westmorland Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Westmorland

More Top-Rated Vacation Rentals in Westmorland Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor space with a spacious patio or deck for relaxing and entertaining.
  • Take advantage of a swimming pool to cool off during warm summer days in the region.
  • Benefit from a well-maintained yard or garden area perfect for outdoor activities or picnics.
  • Make use of outdoor grilling equipment to prepare meals while soaking in the scenic surroundings.
  • Explore nearby walking trails or nature paths for outdoor adventures within easy reach.
  • Relax in a cozy fire pit area, ideal for gathering with family or friends after a day of exploring.
  • Secure parking facilities or covered carports to conveniently access your vehicle when staying here.

Top Attractions Around Westmorland

What attractions are nearby?

Within this vibrant region, you can explore a variety of outdoor activities and local attractions that highlight the best of what Lexington has to offer, making it an ideal destination for those seeking an engaging and memorable stay.

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Family Activities

  • Kentucky Horse Park: Discover the region’s rich equestrian heritage with interactive exhibits and horse shows suitable for the whole family.
  • Lexington Children's Museum: Engage your kids with hands-on exhibits and educational activities located in this family-friendly museum here in the area.
  • Waveland Museum & Historic Site: Explore this beautifully preserved historic site that offers engaging tours and outdoor spaces perfect for family outings.
  • Kentucky Equine Education Center: Witness the majesty of horses up close while enjoying educational programs designed to entertain and inform visitors of all ages.
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Adult Activities

  • Visit the Kentucky Horse Park: Immerse yourself in the region's equestrian heritage through up-close encounters with thoroughbreds and expert-guided tours.
  • Explore the Distillery District: Experience the rich history of bourbon production with tastings and guided walks through this iconic area renowned for its craftsmanship.
  • Enjoy live music at local venues: Relax and unwind by attending performances at Lexington's vibrant music venues that showcase the area's diverse cultural scene.
  • Discover the Arboretum: Stroll through beautifully maintained gardens and natural trails, perfect for peaceful afternoons amid the region’s lush landscape.

Westmorland Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Embrace the flavors unique to Lexington by trying local eateries and markets, which can enhance your stay in this vibrant region.
  • Plan Outdoor Activities: Take advantage of the area's natural scenery and outdoor spots for activities like hiking or picnicking to experience Westmorland fully.
  • Visit Seasonal Events: Check out festivals or local gatherings happening during your visit, offering authentic cultural experiences here.
  • Choose Well-Located Vacation Rentals: Opt for accommodations near key attractions or convenient transportation routes to maximize your leisure time in the region.

Transportation Options

  • LexTran Bus Service: A convenient public transportation option for exploring the area, offering affordable fares and routes connecting key neighborhoods and attractions.
  • Private Car Services: Reliable taxi and ride-share services provide flexible and comfortable transportation around this destination, ideal for quick trips or airport transfers.
  • Rental Cars: Renting a vehicle offers the freedom to explore the region at your own pace, with numerous rental agencies available nearby for seamless pick-up and drop-off.
  • Cycling and Pedestrian Paths: Well-maintained bike lanes and walking trails make it easy to enjoy the local scenery while getting around in a healthy and environmentally friendly way.

Local Customs Options

  • Kentucky Derby Traditions: Participating in local festivities during the Kentucky Derby is a cherished custom, reflecting the area's rich horse racing heritage.
  • Southern Hospitality: Expect warm welcomes and friendly interactions, as hospitality is a fundamental aspect of the region's cultural identity.
  • Mason County Cattlemen’s Festival: Engaging in this annual celebration showcases the area's agricultural roots and community spirit.
  • Local Bluegrass Music: Enjoying live bluegrass performances is a common pastime, highlighting the area's musical legacy and love for vibrant, traditional sounds.

Frequently Asked Questions About Westmorland?

1. What are the top vacation rentals in Westmorland?

There are a lot of options in Westmorland. If you plan on staying in the Westmorland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Westmorland:

2. How many vacation rentals have private pools in Westmorland?

There are 15 vacation rentals with private pools near Westmorland. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Westmorland are best for families?

If you are looking for a family-friendly vacation home in Westmorland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Westmorland:

4. How many Rentbyowner vacation rentals are available in Westmorland?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 294 in the Westmorland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Westmorland. 

5. What is the cancellation policy for vacation rentals in Westmorland, Lexington?

The cancellation policy varies depending on the property listing. You should review the specific terms outlined in the rental agreement or contact the property owner directly to understand the conditions and any applicable fees.

6. Are there any specific house rules I should be aware of when booking here?

Yes, each vacation rental has its own set of house rules which are detailed in the listing. Be sure to read these carefully before booking to ensure a smooth stay and comply with the host’s requirements.

7. How do I find available dates and rates for my stay?

Availability and pricing are updated regularly on the listing page. Select your desired dates to view current rates and availability, or reach out to the owner if you have specific questions.

8. Is there a minimum stay requirement for booking in this region?

Minimum stay policies vary by property. Some listings may require a certain number of nights, so it’s best to check the specific property details or contact the owner directly for confirmation.

9. What amenities are typically included in vacation rentals in this area?

Amenities differ between properties, but common features include Wi-Fi, parking, kitchens, and outdoor spaces. To see what’s offered, review the amenities listed on the property page or contact the owner for more information.