What are the top rated Cottage Rentals in Osterville?

There are a lot of options in Osterville. If you plan on staying in the Osterville area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Osterville: <a href="/property/beautiful-and-private-osterville-home-large-game-room-ac-parking/HA-1214634719" class="class="static-page-link"">BEAUTIFUL and PRIVATE OSTERVILLE HOME, LARGE GAME ROOM, AC,PARKING</a> <a href="/property/lovely-osterville-home-with-new-gunite-pool-and-beach-pass/HA-1214244679" class="class="static-page-link"">Lovely Osterville Home With New Gunite Pool and Beach Pass.</a> <a href="/property/osterville-newly-renovated-with-central-ac-and-beach-pass/HA-3212855057" class="class="static-page-link"">Osterville~Newly Renovated with central AC and beach pass</a> <a href="/property/osterville-cape-cod-style-home-one-block-from-north-bay/HA-32128433" class="class="static-page-link"">Osterville Cape Cod-Style Home - One Block from North Bay!</a> <a href="/property/osterville-4bd-on-wianno-2nd-fairway-walk-to-village-marina-or-bike-to-beach/HA-321293005" class="class="static-page-link"">Osterville 4BD on Wianno 2nd Fairway! Walk to village/marina or bike to beach.</a> <a href="/property/charming-osterville-getaway-walk-to-village-beach/HA-3212572746" class="class="static-page-link"">Charming Osterville Getaway – Walk to Village &amp; Beach!</a> <a href="/property/the-half-shell-cottage-in-osterville-village/HA-1214383018" class="class="static-page-link"">&#34;The Half Shell&#34; Cottage in Osterville Village</a> <a href="/property/private-nantucket-style-home-with-heated-pool-and-beach-pass/HA-1217916608" class="class="static-page-link"">Private Nantucket style home with heated pool and beach pass</a> <a href="/property/4br-4ba-osterville-home-with-pool-hot-tub-game-room-minutes-from-the-beach/HA-3213160421" class="class="static-page-link"">4BR 4BA Osterville home with pool, hot tub, game room-minutes from the beach!</a> <a href="/property/charming-home-in-osterville-close-to-beach-includes-beach-pass/HA-3212258735" class="class="static-page-link"">Charming home in Osterville close to beach! Includes beach pass</a>

How much does it cost to rent a cottage in Osterville?

The average cost for a cottage rental in Osterville is $333 per night. Bigislandhawaiirental has a wide list of great cottages near Osterville that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Do you have any rental cottages in Osterville that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Osterville to find one that works for you.

Are there quality cottages in Osterville that have indoor swimming pools?

As of 2026, the data from Bigislandhawaiirental shows that there are Over 8 private swimming pools or cottages with indoor pools in the Osterville area along with other great amenities.

Osterville Cottage Rentals By Owner

Charming cottage near Osterville Village and Dowses beach. RPMS094

From US $477

10.0 (1 Review)

Cottage

Charming cottage near Osterville Village and Dowses beach. RPMS094

Air Conditioner
Parking
TV

Osterville Cottage Rentals & Holiday Homes

Find the best cottages in Osterville - We found 8 exact matches

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