Guesthouse vacation rentals in Cumberland County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Cumberland County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Cumberland County guesthouse rentals
Family-friendly guest house rentals
Guesthouse
4.84 out of 5 average rating, 43 reviewsStylish, high end, close to Bowdoin & town
Guesthouse
4.99 out of 5 average rating, 93 reviewsSouth Freeport Village Barn
Guesthouse
4.9 out of 5 average rating, 10 reviewsLocation Location @ Tami Lyns Place
Guesthouse
4.86 out of 5 average rating, 139 reviewsCottage Near the Sea, private with deck
Guesthouse
5 out of 5 average rating, 4 reviewsLakeside, private, Maine experience.
Guesthouse
4.85 out of 5 average rating, 27 reviews1 Block to the Beach!
Private room
4.95 out of 5 average rating, 66 reviewsStone's Throw from the Shore Bunk House
Guest house rentals with a patio
Guesthouse
4.8 out of 5 average rating, 85 reviewsModern stay Westbrook Maine
Guesthouse
4.88 out of 5 average rating, 104 reviewsPrivate apart with luxury view, mins to everything
Guesthouse
4.97 out of 5 average rating, 89 reviewsWillard Beach Guest House Minutes from Everything!
Guesthouse
5 out of 5 average rating, 26 reviewsRiverfront guest house w/ patio
Guesthouse
4.98 out of 5 average rating, 45 reviewsDiscover Minglewood: A Peaceful Couple's Getaway
Guesthouse
4.98 out of 5 average rating, 55 reviewsThe Forested Bohemian . Tiny home/ tree house
Guesthouse
5 out of 5 average rating, 86 reviewsSunny guesthouse in coastal Maine
Guesthouse
4.57 out of 5 average rating, 7 reviewsFun and Sun Cozy Cabin-short walk to beach
Guest house rentals with a washer and dryer
Guesthouse
4.89 out of 5 average rating, 93 reviewsHarraseeket Estuary Loft Apartment
Guesthouse
5 out of 5 average rating, 29 reviewsSpruce Ledge Boathouse
Guesthouse
4.75 out of 5 average rating, 36 reviewsCamp in the woods in a luxury RV camper
Guesthouse
5 out of 5 average rating, 8 reviewsGuest house, dead end Prouts Neck, Scarborough
Guesthouse
4.99 out of 5 average rating, 126 reviewsPrivate Guesthouse in the Woods
Guesthouse
4.97 out of 5 average rating, 35 reviewsDowntown Freeport Barn’acle
Guesthouse
4.88 out of 5 average rating, 8 reviewsCharming Maine Country Cottage on Candlewick Lane
Guesthouse
5 out of 5 average rating, 37 reviewsCozy 2BR retreat min toUSM&Sebago
Destinations to explore
- Guesthouse rentals United States
- House rentals United States
- House rentals Maine
- Guesthouse rentals Maine
- House rentals New Hampshire
- Guesthouse rentals New Hampshire
- House rentals Portland
- House rentals Salem
- Rentals with a patio Cumberland County
- Cabin rentals Cumberland County
- Waterfront rentals Cumberland County
- Rentals with breakfast Cumberland County
- Fitness-friendly rentals Cumberland County
- Rentals with lake access Cumberland County
- Ski-in/ski-out rentals Cumberland County
- Rentals with a washer and dryer Cumberland County
- Kid-friendly rentals Cumberland County
- Rentals with beach access Cumberland County
- Cottage rentals Cumberland County
- Rentals with an accessible height toilet Cumberland County
- Tiny house rentals Cumberland County
- Condo rentals Cumberland County
- Rentals with pools Cumberland County
- Monthly Rentals Cumberland County
- Rentals with outdoor seating Cumberland County
- Rentals with a hot tub Cumberland County
- Villa rentals Cumberland County
- Rentals with an EV charger Cumberland County
- Rentals with a kayak Cumberland County
- Townhouse rentals Cumberland County
- Rentals with a fire pit Cumberland County
- Beachfront rentals Cumberland County
- Farmstay rentals Cumberland County
- Rentals with a sauna Cumberland County
- Private suite rentals Cumberland County
- House rentals Cumberland County
- Rentals with a fireplace Cumberland County
- Pet-friendly rentals Cumberland County
- Apartment rentals Cumberland County
- Yurt rentals Cumberland County
- Bed and breakfasts Cumberland County
- Family-friendly rentals Cumberland County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do United States
- Art and culture United States
- Entertainment United States
- Sports activities United States
- Food and drink United States
- Sightseeing United States
- Nature and outdoors United States
- Wellness United States
- Things to do Maine
- Nature and outdoors Maine
- Things to do Cumberland County
- Art and culture Cumberland County
- Nature and outdoors Cumberland County