Cumberland County Cottage Rentals & Holiday Homes
Find the best cottages in Cumberland County - We found 431 exact matches
About Cumberland County Luxury Rental on Caribbean Daily
Searching for cottages to rent near Cumberland County? Caribbean Daily features more than 431 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Cumberland County have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Caribbean Daily’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Cumberland County.
Are you planning to travel to the lakeside, beach, or mountain area? Caribbean Daily’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Caribbean Daily boasts of 431 holiday cottages and places to stay in Cumberland County. The site provides unique Airbnb, VRBO, Caribbean Daily-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Cumberland County Cottage Rentals
What are the top rated Cottage Rentals in Cumberland County?
There are a lot of options in Cumberland County. If you plan on staying in the Cumberland County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Cumberland County:
- Sunny Cottage on Private Oceanfront Point
- PLEASE READ REVIEWS of SEBAGO LAKE COTTAGE - 2026 BOOKINGS BEGINNING Oct 1, 2025
- Wooded Highland Lake Waterfront Cabin - Great Beach and Dock
- 'Camp Card Cove' the Way Life Should Be
- Authentic with Luxury Amenities With 250 Ft Of Private Sandy Frontage On Sebago
- Hollywood meets seaside charm in the former cottage of famed director, John Ford
- Lovely Long Lake Cottage
- Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location
- Lake/Mountain View-Highland Lake Waterfront 3 Bedroom Cottage
- Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch
How much does it cost to rent a cottage in Cumberland County?
The average cost for a cottage rental in Cumberland County is $402 per night. Caribbeandaily has a wide list of great cottages near Cumberland County that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Cumberland County that allow pets?
Yes, here are the top cottage rentals in Cumberland County that allow you to bring your pet:
- THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
- Scenic View Cottage
- Lovely 3-bedroom cottage with dock and lake frontage on Long Lake in Bridgton
- Lakefront Cottage - private dock, large decks, large fire pit
See all pet-friendly vacation rentals in Cumberland County on Caribbeandaily
Do you have any rental cottages in Cumberland County that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Cumberland County to find one that works for you.
Are there quality cottages in Cumberland County that have indoor swimming pools?
As of 2026, the data from Caribbeandaily shows that there are Over 431 private swimming pools or cottages with indoor pools in the Cumberland County area along with other great amenities.
