Castlewood holiday rentals

We found 41 holiday rentals — enter your dates for availability

Discover a selection of 7 homes and other holiday rentals in Castlewood that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there holiday rentals in Castlewood?
Yes, there are holiday rentals close to the most popular sights in Castlewood, or you can select a more secluded option if you're looking for a relaxing stay.
How many holiday rentals are there in Castlewood?
Choose from 7 Expedia holiday rentals in Castlewood for a memorable holiday.
What's there to see and do in Castlewood?
Explore the area and cultural attractions such as Kentucky Horse Park, or visit one of the family-friendly sights such as Lexington Ice Center. Loudoun House and Transylvania University are a couple of places you'll find in the wider area.
What's a holiday rental in Castlewood like?
Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castlewood. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.

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