Best Places to Stay in Old Orchard Beach with Family

Old Orchard Beach is a family beach town and has been for a hundred years. Seven miles of flat sand, a working pier, an amusement park (Palace Playland), a Ferris wheel you can see from the beach, and a pizza-and-ice-cream main drag that kids navigate without a map. For a family trip, where you stay comes down to one question: can the kids walk to the sand in bathing suits? Here are five Everrow rentals that pass that test.

The OOB Lay of the Land

The town is long and narrow. The pier is the center — Palace Playland and the biggest restaurant cluster sit right there. Walk two blocks south and you’re at the “quieter” stretch (still a beach town, just less carnival). The north end, past the pier, has its own cottage-colony feel. A great family trip leans into one end and stays put; driving between them feels like a lot with kids.

What Makes a Great OOB Family Rental

Walk to the beach in bathing suits. Enough bedrooms that kids aren’t on cots in the living room. A parking spot — street parking in OOB in July is brutal. A yard or outdoor space for the Popsicle-drip shower-off moment. Air conditioning — OOB gets hot.

Five Family Picks in Old Orchard Beach

1. Little Miss Cottages — Two Bedroom Cottage (OOB)

• Best for: a classic OOB cottage-colony experience with young kids

Price tier: $$

The Little Miss Cottages compound is exactly what a kid pictures when they hear “beach cottage” — small, cute, one step from sand. The two-bedroom is the workhorse family option.

• Walk to the beach
• Cottage-colony layout
• One-level, stroller-friendly

2. Little Miss Cottages — One Bedroom Cottage (OOB)

• Best for: families of 3 or grandparents joining

Price tier: $

A smaller cottage in the same colony. A smart pick for a small family or as the second cottage when multiple family units are traveling together (book two side-by-side).

• Same walk-to-beach setup
• Small-footprint, budget-friendly
• Pair with a neighboring cottage for a multigenerational trip

3. Tideside House — 4BR Walk to Beach

• Best for: larger families or two families splitting a week

Price tier: $$$

Four bedrooms, a yard, and a walk to the beach. Tideside is the “everyone under one roof” house for the family trip where cousins are invited.

• Four bedrooms
• Walk to the beach
• Yard for backyard time

4. Heart of Old Orchard — 2BR Walk to Beach & Pier

• Best for: families who want to be in the middle of the OOB scene

Price tier: $$

Central OOB means walk-to-Palace-Playland, walk-to-pier, walk-to-arcade. The trade-off is noise and energy — exactly what some families want.

• Central OOB location
• Walk to Palace Playland
• Two bedrooms

5. Charming Centrally Located Seaside Retreat (OOB)

• Best for: a smaller family wanting a “cute old-OOB cottage” feel

Price tier: $$

A central OOB cottage with charm and proximity — the kind of rental where the photos don’t oversell and the location delivers. Good pick for a long-weekend family trip.

• Central location
• Walk to beach and pier
• Classic seaside cottage feel

Plan Your Trip

When should we go?

Late June through Labor Day is peak; July and early August have the warmest water.

Book how far out?

90+ days for July weekends.

Rainy-day plan?

Funtown Splashtown USA (10 min), Maine Aquarium (20 min).

Where do locals eat?

Joseph’s by the Sea (fancy), Rapid Ray’s (takeout), Beach Bagels (breakfast).

Keep planning: explore Maine with kids, the Maine coast, or near Portland.

Looking for the right rental or considering hosting?

Whether you’re planning a stay or thinking about putting your own Maine home on the market, Everrow can help. Browse our curated collection of vetted rentals, or learn how our full-service management turns the right property into a reliable year-round business.