Bailey Island Cottage Rentals & Holiday Homes
Find the best cottages in Bailey Island - We found 83 exact matches
About Bailey Island Luxury Rental on Weekend Getaways
Searching for cottages to rent near Bailey Island? Weekend Getaways features more than 83 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 Bailey Island 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. Weekend Getaways’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Bailey Island.
Are you planning to travel to the lakeside, beach, or mountain area? Weekend Getaways’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.
Weekend Getaways boasts of 83 holiday cottages and places to stay in Bailey Island. The site provides unique Airbnb, VRBO, Weekend Getaways-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 Bailey Island Cottage Rentals
What are the top rated Cottage Rentals in Bailey Island?
There are a lot of options in Bailey Island. If you plan on staying in the Bailey Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Bailey Island:
- Tidal Cove- Informal Charming Cottage Rebuilt to Passive Cozy
- Adorable cottage with million dollar view and short walk to stunning beach.
- Step off the deck to enjoy the beach & a short walk down the scenic peninsula ~
- Charming 4 bedroom Classic Maine Cottage located near the giant stairs.
- The Auburn Colony is for the vacationer who wants to tap into the history and traditions of colon.
- Cozy oceanfront cottage on Orr's Island
- Waterfront Family Bungalow on Beautiful Potts Harbor
- Henry's HideaWay Harpswell
- HARPSWELL MAINE - The Cottage @ AshPoint
- Private Water Access and Dock, Amazing Sunsets and Ocean Views in Historic House
How much does it cost to rent a cottage in Bailey Island?
The average cost for a cottage rental in Bailey Island is $370 per night. Weekendgetaways has a wide list of great cottages near Bailey Island that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Bailey Island that allow pets?
Yes, here are the top cottage rentals in Bailey Island that allow you to bring your pet:
- THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
- PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
- Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views! Max 2 people.
- The Little House - Gorgeous Views of Lowell's Cove and Casco Bay
See all pet-friendly vacation rentals in Bailey Island on Weekendgetaways
Do you have any rental cottages in Bailey Island that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Bailey Island to find one that works for you.
Are there quality cottages in Bailey Island that have indoor swimming pools?
As of 2026, the data from Weekendgetaways shows that there are Over 83 private swimming pools or cottages with indoor pools in the Bailey Island area along with other great amenities.
