Where to Stay in Portland, Maine

We’re locals (Portland, Maine residents 👋), so these are the stays we recommend when friends and family ask, “Okay but where should we actually stay?” Whether you want to be steps from Old Port restaurants, wake up near the waterfront, or book a boutique hotel that feels like part of the trip, these are our favorite picks.

1) Longfellow Hotel

Vibe: Boutique-luxe and design-forward.

Why we love it: The Longfellow feels like a true treat—beautiful design, calm energy, and a great home base for exploring. We also love the lobby bar, Five of Clubs, and breakfast and lunch spot, Twinflower Cafe.

Best for: Couples weekends, solo stays, or anyone who loves a polished boutique hotel vibe.

2) Weldon Hotel

Vibe: Modern, minimal, and city-chic.

Why we love it: Weldon is an easy, stylish pick for a Portland weekend— a great location, and perfect if your plan is to spend most of your time eating and exploring your way through the city. The kitchen and multiple bedrooms also makes this the perfect stay for families and groups.

Best for: Friend or family trips or travelers who want a modern stay close to the action.

3) Canopy by Hilton Portland Waterfront

Vibe: Waterfront convenience with a contemporary feel.

Why we love it: If you want to be near the harbor and walk straight into Old Port energy, Canopy is a great option. It’s comfortable, well-located, and ideal for exploring without a car—especially if waterfront walks are part of your weekend plan.

Best for: First-time visitors, weekend explorers, and anyone who wants an easy stay in a prime spot.

4) Press Hotel

Vibe: Iconic boutique luxury with character—historic + artsy + elevated.

Why we love it: The Press is still on our bucket list to stay at, but it is one of the most Portland hotels you can book—beautiful design details and that elevated boutique feel that still reads cool and creative.

Best for: Celebrations, romantic weekends, and travelers who love hotels with personality.

Bonus: The Lincoln Hotel

Vibe: Cool, design-forward, and a little unexpected—boutique with a fun social energy.

Why we love it: The Lincoln is a great option if you want a stay that’s perfectly positioned between destinations. Located in Biddeford, it’s convenient for doing Portland (food + Old Port) and making a day trip down the coast toward Kennebunkport. It also has a rooftop pool (a rare find in Maine!) and Batson River on-site, which makes it easy to turn your stay into a full “hang at the hotel” moment—pool time, cocktails, and dinner without needing to plan a thing.

Best for: Weekend explorers who want a central home base, couples or friends who love a rooftop pool, and travelers who want a stylish stay with built-in dining.

If you have extra time to explore on your trip, be sure to check out our other Maine itineraries and travel guides:

• Kennebunk and Kennebunkport, ME
• Ogunquit and York, ME
• Portland, ME Summer and Fall Travel Guide
• Portland, ME Family Friendly Weekend Guide

Thank you for visiting our site! Our recommendations included hosted stays and we may make commission off affiliate links (at no further cost to you), but we would never recommend a place we don’t genuinely want to recommend.

– Karen and Kasey