Owings Cottages
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Cottages in Owings

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Family and Pet-Friendly, Waterfront with Pier

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
Owings Cottage Accommodation
You’re on the go every day, working hard and making that cash. But if you haven’t taken a holiday in months, it’s time to rethink your life choices. It’s time for you to look into Owings holiday cottages and take a day off—or ten days. Because once you’re all settled in, you won’t want to leave.
Words like charming, adorable, and delightful probably come to mind when you think of country cottages, set in lovely little towns the world over. The same applies to beach cottages—just replace the rolling hills with lapping waves. And while Owings cottages can’t be in every setting at once, you’ll find that the stunning scenery here is better than all the others combined. Cottages are the perfect retreat from everyday life, with serene surroundings both inside and out and that relaxed vibe that can come only from knowing everything is taken care of. Owings has an equally charming vibe, and that’s why so many travellers love it.
“Don’t worry, be happy” should be your motto on your next holiday. Well, friend, in Owings, that’s not just the motto of visitors; the locals are living that theme every day. So take a break from that presentation you’re working on and make a different graph instead—of Wotif’s low prices on over Owings cottage accommodation options. It’s about time you got to kick back, and we don’t mean putting your feet up at your desk.
Owings Cottages essential information
Accommodation | 74 Cottages |
|---|---|
Lowest Price | NZ$135 |
Highest Price | NZ$945 |
Popular accommodation | John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE, Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Family and Pet-Friendly, Waterfront with Pier, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK, Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly), Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly, Your Annapolis Waterfront retreat for a weekend or any-day getaway! |
Top trending hotels in Owings

Graduate by Hilton Annapolis
^Eligibility requirements and conditions apply







