Maine is bigger than you think. The drive from Kittery to Fort Kent takes longer than Boston to Washington, D.C. The coast is a different country from the ski towns, and the lakes are a third thing entirely. The best place to stay in Maine depends entirely on what you came for — beaches and lobster rolls, ski weekends, fall foliage, a quiet lake. This guide lays out the five regions worth your time and names one flagship Everrow rental in each.
The Bottom Line: Maine splits into six distinct regions — coast, Portland, lakes, mountains, the Kennebunks, and Downeast — and the right one depends on whether you want surf, ski, foliage, or family lake time. This guide maps all six with a rental pick for each.
How to Use This Guide
If you have a weekend, pick one region. If you have a full week, combine two — Portland plus the coast, or Sugarloaf plus the lakes. Maine rewards slow travel; don’t try to see all five in one trip.
1. Greater Portland — The Cultural and Culinary Hub
Portland is a walkable peninsula packed with restaurants, galleries, and historic neighborhoods, two hours north of Boston. Use it as a base for day trips to the Kennebunks and Cape Elizabeth, or let it eat a full three days on its own merits.
Flagship pick — State of Mind, West End, Portland.
A landmark West End home on a tree-lined block, ten minutes on foot to the Old Port. The kind of stay that makes the trip feel intentional rather than just booked.
- West End’s most photogenic block
- Walk to Local 188, Sur Lie, Duckfat
- Sleeps a small group comfortably
Deeper dive: Where to Stay in Portland, Maine.
2. Sunday River / Bethel — The Winter and Golf Capital of Western Maine
Bethel sits at the foot of Sunday River, Maine’s largest ski resort by skiable acreage, and the broader town is a year-round basecamp — skiing in winter, golf and hiking in summer, foliage in fall. About three hours from Boston.
Flagship pick — The Epic Sunday River Getaway, Bethel.
A purpose-built group home minutes from Sunday River’s lifts. Designed for crews that want one roof, a real kitchen, and enough space that nobody gets in anyone’s way.
- Minutes to Sunday River base areas
- Built for groups with a proper kitchen and living space
- Year-round appeal — skiing, golf, fall foliage
Deeper dive: Best Places to Stay Near Sunday River for Skiing.
3. Sugarloaf / Carrabassett Valley — The Backcountry Alternative
Sugarloaf is the second-largest ski mountain in New England by skiable acreage and the quieter alternative to Sunday River. Carrabassett Valley is also home to some of the best mountain biking in the country at the Carrabassett Region trails. About three and a half hours from Boston.
Flagship pick — Summit Haus, Liftside Penthouse at Sugarloaf.
A true ski-in convenience penthouse — boots off, lift up. For travelers who value proximity to the snow over anything else.
- Liftside access to Sugarloaf terrain
- Penthouse-level finishes and views
- Four-season base for golf, MTB, and foliage
4. The Maine Coast / Old Orchard Beach — Classic Summer
Seven miles of sand, a working pier, and a low-key beach-town vibe, 20 minutes south of Portland. Old Orchard Beach is the Maine coast if you want a beach vacation without having to book a year in advance.
Flagship pick — Tideside House, Old Orchard Beach.
A four-bedroom house you can walk to the beach from — the classic Maine summer setup. Room for a real family trip or two couples splitting a week.
- Walk to the beach and OOB pier
- Four bedrooms, built for families
- Close to Palace Playland and OOB’s summer scene
Deeper dive: Best Places to Stay on the Maine Coast.
5. The Maine Lakes Region — Quiet Water
The Belgrade Lakes area in central Maine is a chain of connected ponds and lakes that’s been summer-camp country for a century. Quieter than the coast, perfect for paddling, fishing, and reading a long book. About two hours from Portland.
Flagship pick — The Tipsy Moose, Mount Vernon.
An “ayuh” Maine lakeside lodge — exactly the kind of slow-pace lake getaway people picture when they imagine Maine. Kayaks in the water, porch with a view, and a lake that feels like a private club.
- Private lakefront with water access
- Classic Maine lodge aesthetics
- Two-hour drive from Portland or Boston
Deeper dive: Best Places to Stay in the Maine Lakes Region.
How to Pick
First trip to Maine? Portland + one day trip to the coast.
Ski trip? Sunday River for amenities, Sugarloaf for terrain.
Family beach week? Old Orchard Beach.
Quiet reset? The Lakes Region.
Fall foliage? Bethel or Sugarloaf — see our fall guide.
Maine doesn’t have one best place to stay. It has five.
Keep planning: explore Portland neighborhoods, the Maine coast, or New England.
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.
