Homewood Summer Rentals, Cottages & Cabins
Book a Place to Stay in Homewood for Your Summer Getaway
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About Homewood Summer Rental on PickleTrip
PickleTrip™'s summer rentals in Homewood are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.
Enjoy the perfect summer vacation in Homewood with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.
Frequently Asked Questions About Homewood Luxury Rentals
There are a lot of options in Homewood. If you plan on staying in the Homewood area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Homewood:
- 6 Mi to Dtwn: Family-Friendly Home in Annapolis!
- Annapolis waterfront "tiny house" in garden setting
- Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
- Stunning Waterfront Cottage with Breathtaking Views!
- PERFECT LOCATION in the heart of history
- The Yellow Cottage on Harness Creek
- Upscale home with parking for 4 cars in driveway. Walk to downtown.
- Your Annapolis Adventure Starts Here!
- Historic Downtown Charmer, Water Views and Parking!
- 421 Irie: Simply Charming 2 Story COTTAGE! Private Pool! 1 Off Street Parking!
Yes, here are some popular summer holiday rentals in Homewood that have a private or indoor pool:
- 6 Mi to Dtwn: Family-Friendly Home in Annapolis!
- Harrison Hall
- Inn at Horn Point
- Coastal Cottage in West Annapolis
Check all holiday rentals with a pool in Homewood on PickleTrip.
Yes, We have 514 summer rental homes in Homewood and types of place to stay in Homewood include:
- Vacation Homes: 514 available for rent
- Villas: 514 Rentals available for rent
- Holiday Apartments: 514 Rentals available for rent
- Hotels with Suites: 514 Rentals available for book
