Head of The Bay Cottage Rentals & Holiday Homes

Find the best cottages in Head of The Bay - We found 122 exact matches

About Head of The Bay Cottage Rentals on PickleTrip

Searching for cottages to rent near Head of The Bay? PickleTrip™ features more than 122 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. These cottage rentals in Head of The Bay 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. PickleTrip™’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Head of The Bay.

Are you planning to travel to the lakeside, beach, or mountain area? PickleTrip™’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.

PickleTrip™ boasts of 122 holiday cottages and places to stay in Head of The Bay. The site provides unique Airbnb, VRBO, pickleball-ready 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.

Show more
Show less

Frequently Asked Questions About Head of The Bay Rental Cottages

The average cost for a cottage rental in Head of The Bay is $1,174 per night. PickleTrip has a wide list of great cottages near Head of The Bay that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Head of The Bay that allow you to bring your pet:

See all pet-friendly vacation rentals in Head of The Bay on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Head of The Bay to find one that works for you.
As of 2025, the data from PickleTrip shows that there are Over 122 private swimming pools or cottages with indoor pools in the Head of The Bay area along with other great amenities.
About 122 cottages in Head of The Bay boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Head of The Bay on PickleTrip
Yes, there are luxury cottages in Head of The Bay. Find more luxury, lakefront, winter, & last-minute cottage rentals near Head of The Bay.