Popular Vacation Homes Near Hillsborough County
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Popular Vacation Homes Near Hillsborough County

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Trip.Best is a collection of travel rankings that takes into account the travel choices and genuine preferences of hundres of millions of Trip.com users. It is updated monthly based on real data.
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Best vacation homes in Hillsborough County (2025)

Looking for the perfect home-away-from-home in Hillsborough County? From modern apartments to spacious villas, Hillsborough County offers an exceptional collection of vacation homes that blend comfort, privacy, and convenience.

Whether you're here for a family holiday, group trip, or a long-term stay, these top-rated properties promise a relaxing and flexible experience.

Top-rated vacation homes in Hillsborough County

If you prefer the comfort and freedom of a fully equipped home, these vacation homes deliver the ideal experience. Expect spacious living areas, kitchens, private terraces, and amenities suited for travelers of all ages.

The Trellis House

• Ogunquit | 98.3 km from Hillsborough County

The 1770 House Restaurant & Inn

• East Hampton | More than 100 km from Hillsborough County

Rockland Talbot House

• Rockland | More than 100 km from Hillsborough County

Vacation homes with exceptional comfort

These homes provide flexibility and independence while maintaining comfort and style. Enjoy fully furnished spaces, private kitchens, and living areas perfect for families, groups, or long stays.

Vacation homes near Hillsborough County

If you want a home-style stay just outside Hillsborough County, there are plenty of vacation homes that combine privacy with easy access to the city. These properties are ideal for weekend retreats or extended stays with family or friends.

Each of these properties offers a unique stay within 1–3 hours of Hillsborough County, perfect for travelers seeking independence, privacy, and comfort.

What makes Hillsborough County’s vacation homes special

• Home comforts: Fully equipped kitchens, living areas, and private spaces.
• Flexibility & privacy: Ideal for families, groups, or long-term stays.
• Convenient locations: Close to city attractions, restaurants, and transport.
• Relaxed atmosphere: Spacious interiors and personalized accommodations.

Tips for booking vacation homes in Hillsborough County

1. Visit during off-peak periods for better availability and pricing.
2. Book early for popular properties, especially during holidays.
3. Compare prices and packages on Trip.com for deals, loyalty points, and flexible booking options.
4. Consider properties with essential amenities like parking, Wi-Fi, and kitchen facilities.

Book your stay at Hillsborough County's best vacation homes

Ready to enjoy the freedom of a vacation home in Hillsborough County? Explore Trip.Best's curated list of vacation homes and experience privacy, comfort, and convenience.

Book your perfect home-away-from-home on Trip.com today, where independence and comfort meet.

What are some Vacation Homes near Hillsborough County?
Some Vacation Homes near Hillsborough County include:The Trellis House, The 1770 House Restaurant & Inn, Rockland Talbot House, Captain Nickels Inn
What are some highly-rated Vacation Homes near Hillsborough County?
Some highly-rated Vacation Homes near Hillsborough County include:The Trellis House:10.0, The 1770 House Restaurant & Inn:9.7, Rockland Talbot House:8.8, Captain Nickels Inn:9.8
Where are Vacation Homes near Hillsborough County located?
The Vacation Homes near Hillsborough County are mainly located in:The Trellis House:Ogunquit, The 1770 House Restaurant & Inn:East Hampton, Rockland Talbot House:Rockland, Captain Nickels Inn:Searsport
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