Haskell Cottages
Waterfront weekly rentals on Little Deer Isle, managed by Cris Haskell Rentals. Penobscot Bay views, Haskell District Road addresses, old Maine cottage character. Not for spontaneous travelers — weekly rentals only, book well in advance.
The Haskell name runs deep on Little Deer Isle. The Haskell District Road area on the southern end of the island has been home to the family for generations, and the rental cottages managed under Cris Haskell Rentals reflect that long tenure.
The portfolio includes properties like Periwinkle Cottage (on Haskell District Road, directly on Penobscot Bay shores), Serendipity Serenity Cottages (at Blastow Cove, with views across the bay), and Shore Cottage (a fully remodeled 2-bedroom on the bay). All are weekly rentals.
Little Deer Isle is connected to Deer Isle by a small causeway bridge and has a quieter character than the main island — less traffic, more private coves, a genuine sense of remove. The views across Penobscot Bay toward the Camden Hills and the islands are some of the best on the peninsula.
The historic Squire Ignatius Haskell House in central Deer Isle — now the Pilgrim's Inn — is a landmark tied to the wider Haskell family legacy, which dates back to the original settlement of the island.
Local Tips
- These are weekly rentals only — not suitable for a two-night stop.
- Contact Cris Haskell Rentals directly: crishaskellrental.com
- Availability in peak summer fills up fast. Book for 2026 as early as possible.
- Little Deer Isle is the quieter, more residential part of the island; you'll want a car for everything.
Connected To
- Pilgrim's Inn — the Squire Ignatius Haskell House, a historic landmark with ties to the same family
- Little Deer Isle causeway — the bridge connecting Little Deer Isle to the main island
- Eggemoggin Reach — the tidal passage separating Deer Isle from the mainland; visible from Haskell District Road