Experiences · Hiking & Biking

Hiking & Biking vacation rentals, managed by local experts.

Check off your bucket list with these destinations

Hiking & Biking

Where to go

Hiking & Biking destinations in the Collection

Each destination is represented by a trusted local partner.

Chincoteague

Seaside Vacations & Sales

Chincoteague, VA

Home to wild ponies that have roamed freely for hundreds of years, this virtually untouched natural landscape is a draw for fishers and boaters.

See hiking & biking homes
Kiawah Island

Akers Ellis Real Estate & Rentals

Kiawah Island, SC

A serene and upscale vacation destination renowned for its pristine beaches, world-class golf courses, and abundant natural beauty along the South Carolina coast.

See hiking & biking homes
Sunriver

Arrived Sun River

Sunriver, OR

Here the unspoiled beauty of nature merges with thrilling adventures, a perfect retreat for travelers seeking serenity and excitement.

See hiking & biking homes

Plan your trip

Planning a hiking & biking getaway

Original, destination-informed guidance written with partner input.

01

Choose your region

Compare seasons, highlights and the kind of trip you want.

02

Pick a home for the group

Bedrooms, shared spaces and distance to what you came for.

03

Ask your local partner

Partners can point you to local favorites.

04

Book direct

No commissions from The 100 Collection, and you keep the relationship with the local team.

Questions

Hiking & Biking trip FAQs

What makes a good hiking & biking trip rental?

Space for the whole group, a short drive to what you came for, and a local team that can help with trip questions.

Can I book directly with the local manager?

Yes. The 100 Collection sends you to the partner’s own website, so you book direct with the local professionals.

Are all hiking & biking destinations in the same season?

Best seasons vary by destination, so each destination page includes timing.

Does The 100 Collection manage these homes?

No. Each home is managed by a vetted local partner.

Keep exploring

More experiences

Browse related activity pages across the Collection.

Get hiking & biking trip ideas by email

Choose hiking & biking and we’ll send destination picks from local partners.

The 100 Collection™ 2026