
Guest house holiday rentals in Cumberland County
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Top-rated guest house rentals in Cumberland County
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for guest house rentals in Cumberland County
Family-friendly guest house rentals

Charming Portland Getaway

MountainGate Farm ~Tranquility, relaxation await…

Hobby Farm Guest House

Cozy Home Base

South Freeport Village Barn

Lake Front Cottage w/ Beach Sleeps 4 in Naples

Hidden Gem, Close to Everything, Sparking + Chic

2-BR Charming Lakefront Apartment with W/D
Guest house rentals with a patio

North Coast Retreat | New Near Portland & Beaches

Guest house, dead end Prouts Neck, Scarborough

Private Guesthouse in the Woods

Riverfront guest house w/ patio

Discover Minglewood: A Peaceful Couples Getaway

Tranquil riverfront retreat

Cozy Cabin Getaway-Walk to Beach & Fun!

Coastal Garden Escape
Guest house rentals with a washing machine and dryer

Private Country Cottage on large farm property

Stylish, high end, close to Bowdoin & town

Spruce Ledge Boathouse

Camp in the woods in a luxury RV camper

Falmouth Flats Ocean Escape

Spacious 2 Bedroom Suite

Smith Cottage Higgins Beach

Private Hilltop View
Destinations to explore
- Rentals with pools Cumberland County
- Rentals with an accessible-height toilet Cumberland County
- Rentals with lake access Cumberland County
- Ski-in/ski-out rentals Cumberland County
- Rentals with outdoor seating Cumberland County
- Villa rentals Cumberland County
- Rentals with a sauna Cumberland County
- Fitness-friendly rentals Cumberland County
- Rentals with a fireplace Cumberland County
- Tiny house rentals Cumberland County
- Yurt rentals Cumberland County
- Smoking-friendly rentals Cumberland County
- Family-friendly rentals Cumberland County
- Rentals with a patio Cumberland County
- Cabin rentals Cumberland County
- Rentals with a firepit Cumberland County
- Apartment rentals Cumberland County
- Beachfront rentals Cumberland County
- House rentals Cumberland County
- Motorhome rentals Cumberland County
- Waterfront rentals Cumberland County
- Lakehouse rentals Cumberland County
- Rentals with breakfast Cumberland County
- Rentals with an EV charger Cumberland County
- Rentals with a washing machine and dryer Cumberland County
- Townhouse rentals Cumberland County
- Flat rentals Cumberland County
- Rentals with a kayak Cumberland County
- Boutique hotel rentals Cumberland County
- Rentals with beach access Cumberland County
- Pet-friendly rentals Cumberland County
- Farm stay rentals Cumberland County
- Cottage rentals Cumberland County
- Rentals with a hot tub Cumberland County
- Private suite rentals Cumberland County
- Bed and breakfasts Cumberland County
- Guest house rentals Maine
- Guest house rentals United States
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Story Land
- Scarborough Beach
- Long Sands Beach
- York Harbor Beach
- Attitash Mountain Resort
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- Diana's Baths
- Pemaquid Point Lighthouse
- Dunegrass Golf Club
- East End Beach
- Funtown Splashtown USA
- Crescent Beach State Park
- Laudholm Beach
- Parsons Beach
- Cliff House Beach
- Ferry Beach
- White Lake State Park
- Wolfe's Neck Woods State Park
- Short Sands Beach
- Things to do Cumberland County
- Art and culture Cumberland County
- Sightseeing Cumberland County
- Tours Cumberland County
- Nature and outdoors Cumberland County
- Sports activities Cumberland County
- Things to do Maine
- Tours Maine
- Sightseeing Maine
- Art and culture Maine
- Food and drink Maine
- Sports activities Maine
- Nature and outdoors Maine
- Things to do United States
- Art and culture United States
- Tours United States
- Food and drink United States
- Wellness United States
- Sports activities United States
- Entertainment United States
- Nature and outdoors United States
- Sightseeing United States