Chebeague Island Rentals

Houses, Cottages, Year-Round

Hamilton Management is the island-run rental site for Great Chebeague Island, Maine. Every house here is managed on the island, by people who live on it: readied by island trades, cleaned by island crews, and looked after between guests. Summer weeks, fall and winter stays, and year-round rentals — with one number to call while you're here.

Rental Properties — Coming Soon!

A sunset over Casco Bay, taken from the Chebeague Island Inn, with trees and an umbrella in the foreground.

COMING SOON

3 bed, 2 bath. South Road
$300/night

Silhouettes of people sitting and walking along Indian Point beach during sunset, with a sky transitioning from orange near the horizon to dark blue at the top, scattered clouds, and a visible star.

COMING SOON

2 bed, 2 bath. Fire House Rd
$325/night

A calm body of water at dusk with boats floating, a person paddleboarding, and trees in the foreground. The sky is a gradient of blue and the scene is peaceful and serene.

COMING SOON

4 bed, 2.5 bath. Cottage Road
$450/night

Four kids playing on rocks on Deer Point, Chebeague Island, near a body of water with cliffs and trees in the background under a cloudy sky.

COMING SOON

3 bed, 2 bath. Deer Point Road
$375/night

Schedule a call with us
People sitting around a campfire, with their hands extended towards the flames, at night.

COMING SOON

Yurt & Campsite
$200/night

A beach house Indian Point, Chebeague Island Maine, on a grassy hill with large windows and a chimney, next to a pier extending into water with an American flag, under a partly cloudy sky.

COMING SOON

6 bed, 4 bath. North Road
$5k/week

Questions about what renting your property would look like?

Rental Readiness
& Property Management

Your house earns while you're away, and comes back to you in the condition you left it. We ready it, stage and photograph it, list it on our new Chebeague Rentals platform, market it to guests who love this island in every season, and handle every guest conversation ourselves.

Includes:

  • An honest read before you list. What the house can realistically earn, what it needs first, and what that costs.

  • Set up to rent well. Repairs, upgrades, and a deep clean handled by island trades before the first guest.

  • Listed and marketed. On hamiltonmgt.com and wherever else makes sense for your house.

  • Bookings handled. Inquiries, rates, calendar, guest questions at eleven at night. You're not the one answering.

  • The turn between guests. Cleaned, linens changed, restocked, reset, and inspected twice — once after the clean, once before the guest walks in.

  • Every booking reported, both directions. Including any you take yourself. You see the whole picture, and so do I.

Ready for your property to start paying for itself?