Owner Direct Vacation
Rentals in Chestnut Hill

The Best Owner Direct Vacation Rentals in Chestnut Hill. Explore thousands of vacation home rentals, large cabins, and villas near Chestnut Hill

Explore the Best Chestnut Hill Vacation Homes

Looking for the perfect place to stay in Chestnut Hill? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Chestnut Hill character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.

  • vacation rentals
  • luxury villas
  • beachfront homes
  • pet-friendly rentals
  • condos

Why Travelers Love Using
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Find Chestnut Hill Vacation Rentals

What makes our vacation homes stand out?

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Verified Properties

Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

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Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Wednesday Aug 12

Chestnut Hill, Dandridge

Wed
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24.8°C
Thu
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23.6°C
Fri
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26.2°C
Sat
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26.1°C
Sun
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27.2°C
Mon
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27.2°C
Tue
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24.0°C

Common Vacation Rental Amenities Typical Vacation Rental Amenities

What sort of amenities will be available at your stay?

Our Chestnut Hill vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.

Indoor Amenities

  • indoor-amenities-kitchenFully equipped kitchens
  • indoor-amenities-living-areaSpacious living areas with streaming TVs
  • indoor-amenities-wifiComplimentary Wi-Fi
  • indoor-amenities-acAir conditioning and heating
  • indoor-amenities-washerIn-unit washer and dryer
  • indoor-amenities-bedPlush bedding and comfortable furniture

Outdoor Amenities

  • outdoor-amenities-balconyBalconies or patios with coastal views
  • outdoor-amenities-poolPrivate or shared pools
  • outdoor-amenities-bbqBBQ grills and outdoor dining areas
  • outdoor-amenities-parkingOn-site parking
  • outdoor-amenities-beachEasy access to beaches and attractions

How to Reserve Your Chestnut Hill Vacation Rental

Booking Made Simple

Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.

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SEARCH PROPERTIES

Use filters for location, amenities, and budget.

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VIEW DETAILS

Check photos, reviews, and features for your top picks.

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BOOK SECURELY

Confirm your stay safely through our trusted travel partners.

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Travel Trips for Visiting Chestnut Hill

What should you know when planning a trip to St. Augustine?
  • Book early
    for popular festivals and spring weekends.
  • Pack layers
    Florida weather can change quickly.
  • Stay hydrated
    and plan beach days around midday heat.
  • Explore early
    to avoid crowds at major attractions.
Transportation Around St. Augustine?
  • Driving
    Most convenient for exploring the city and coast.
  • Trolley & Shuttle Tours
    Great for sightseeing and hopping between landmarks.
  • Walking
    The downtown historic district is pedestrian-friendly.
Local Etiquette
  • Respect historic sites and marked paths.
  • Standard U.S. tipping (15–20%) applies.
  • Quiet hours are observed in residential and beachfront areas.

Chestnut Hill Vacation Rental FAQs

What are the top vacation rentals in Chestnut Hill?
How many vacation rentals have private pools in Chestnut Hill?

There are 29 vacation rentals with private pools near Chestnut Hill. Top-rated homes that have access to a swimming pool include:

Which vacation homes in Chestnut Hill are best for families?

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

How many vacation rentals are available in Chestnut Hill?

Currently, the total number of properties listed in 2026 is over 233 in the Chestnut Hill area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chestnut Hill.