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 in Scarborough
4.98 out of 5 average rating, 98 reviewsSmith Cottage Higgins Beach
Dec 2 – 9
Guesthouse in Brunswick
4.83 out of 5 average rating, 42 reviewsStylish, high end, close to Bowdoin & town
Dec 3 – 10
Guesthouse in Hollis Center
4.86 out of 5 average rating, 59 reviewsMoment's Peace Farm Guest House
Dec 20 – 27
Guesthouse in Old Orchard Beach
4.85 out of 5 average rating, 26 reviews1 Block to the Beach!
Jan 12 – 19
Guesthouse in Wales
5.0 out of 5 average rating, 4 reviewsLakeside, private, Maine experience.
Jan 18 – 25
Guesthouse in South Freeport
4.99 out of 5 average rating, 93 reviewsSouth Freeport Village Barn
Dec 6 – 13
Guesthouse in Cape Elizabeth
4.98 out of 5 average rating, 212 reviewsSalty Air in Cape Elizabeth | Portland | Beaches
Oct 23 – 30
Guesthouse in Poland
4.95 out of 5 average rating, 63 reviewsStone's Throw from the Shore Bunk House
Oct 7 – 14
Guest house rentals with a patio
Guesthouse in Falmouth
4.96 out of 5 average rating, 24 reviewsThe Herons Nest at The Mill
Sep 14 – 21
Guesthouse in Westbrook
4.81 out of 5 average rating, 47 reviewsModern stay Westbrook Maine
Dec 15 – 22
Guesthouse in Freeport
4.96 out of 5 average rating, 23 reviewsDiscover Minglewood; a peaceful couple's getaway
Dec 12 – 19
Guesthouse in Westbrook
4.82 out of 5 average rating, 34 reviewsCozy Barn Apartment with Deck and Garden
May 30 – Jun 6
Guesthouse in Yarmouth
5.0 out of 5 average rating, 70 reviewsPrivate Guesthouse in the Woods
Mar 1 – 8
Guesthouse in Brownfield
4.98 out of 5 average rating, 42 reviewsThe Forested Bohemian . Tiny home/ tree house
Oct 16 – 23
Guesthouse in Yarmouth
5.0 out of 5 average rating, 64 reviewsSunny guesthouse in coastal Maine
May 1 – 8
Guesthouse in Bridgton
4.92 out of 5 average rating, 72 reviewsCozy apartment on private road close to everything
Jan 28 – Feb 4
Guest house rentals with a washer and dryer
Guesthouse in Hiram
5.0 out of 5 average rating, 85 reviews1BR cozy, luxurious getaway @ Krista's Guesthouse
Jan 28 – Feb 4
Guesthouse in West Bath
5.0 out of 5 average rating, 15 reviewsSpruce Ledge Boathouse
Oct 23 – 30
Guesthouse in Saco
4.87 out of 5 average rating, 31 reviewsClose Enough - Beach Cottage
Sep 21 – 28
Guesthouse in Gorham
5.0 out of 5 average rating, 20 reviewsCozy 2BR retreat min toUSM&Sebago
May 29 – Jun 5
Guesthouse in Bridgton
5.0 out of 5 average rating, 72 reviewsEscape to the lake!
Nov 19 – 26
Guesthouse in Freeport
4.88 out of 5 average rating, 77 reviewsHarraseeket Estuary Loft Apartment
Aug 9 – 16
Guesthouse in Saco
4.77 out of 5 average rating, 31 reviewsBy the Beach - Cottage
Jun 27 – Jul 4
Guesthouse in Cape Elizabeth
4.85 out of 5 average rating, 124 reviewsBeaches, Sunsets, Tranquil, Lobster, on the Cape
Jun 15 – 22
Destinations to explore
- Guesthouse rentals United States
- House rentals United States
- House rentals Maine
- Guesthouse rentals Maine
- Guesthouse rentals New Hampshire
- House rentals New Hampshire
- House rentals Portland
- House rentals Salem
- Rentals with a patio Cumberland County
- Monthly Rentals Cumberland County
- Rentals with a hot tub Cumberland County
- House rentals Cumberland County
- Townhouse rentals Cumberland County
- Rentals with a kayak Cumberland County
- Yurt rentals Cumberland County
- Family-friendly rentals Cumberland County
- Rentals with outdoor seating Cumberland County
- Kid-friendly rentals Cumberland County
- Rentals with a sauna Cumberland County
- Rentals with lake access Cumberland County
- Beachfront rentals Cumberland County
- Rentals with an accessible height toilet Cumberland County
- Serviced apartment rentals Cumberland County
- Chalet rentals Cumberland County
- Rentals with beach access Cumberland County
- Bed and breakfasts Cumberland County
- Farmstay rentals Cumberland County
- Villa rentals Cumberland County
- Apartment rentals Cumberland County
- Waterfront rentals Cumberland County
- Cottage rentals Cumberland County
- Cabin rentals Cumberland County
- Pet-friendly rentals Cumberland County
- Rentals with pools Cumberland County
- Rentals with a fire pit Cumberland County
- Condo rentals Cumberland County
- Rentals with a home theater Cumberland County
- Fitness-friendly rentals Cumberland County
- Tiny house rentals Cumberland County
- Hotel rentals Cumberland County
- Private suite rentals Cumberland County
- Rentals with breakfast Cumberland County
- Rentals with a fireplace Cumberland County
- Rentals with a washer and dryer Cumberland County
- Rentals with an EV charger 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