Owner Direct Vacation
Rentals in Hillsmere
The Best Owner Direct Vacation Rentals in Hillsmere. Explore thousands of vacation home rentals, large cabins, and villas near Hillsmere
GUESTS
Explore the Best Hillsmere Vacation Homes
Looking for the perfect place to stay in Hillsmere? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Hillsmere character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Parking
- View
- Ocean View
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Hillsmere
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Balcony/Terrace
- Security/Safety
Popular Neighborhoods for Hillsmere Vacation Rentals
What are the best areas to stay in Hillsmere
Discover the top neighborhoods in Hillsmere and choose a place that suits your stay.
Monday Apr 27
Hillsmere, Annapolis
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Hillsmere vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Hillsmere
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
How to Reserve Your Hillsmere Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Hillsmere Vacation Rental FAQs
There are a lot of options in Hillsmere. If you plan on staying in the Hillsmere area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Hillsmere:
- Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
- Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
- PERFECT LOCATION in the heart of history
- Stunning Waterfront Cottage in the Sailing Capital of the World!
- Charming Historic Annapolis Home With Two Off-street Parking Places!
- Renovated Apt In Historic Dist w/2 Parking Spots
- The Yellow Cottage on Harness Creek
- Upscale home with parking for 4 cars in driveway. Walk to downtown.
- 421 Irie: Simply Charming 2 Story COTTAGE! Private Pool! 1 Off Street Parking!
- Historic Downtown Charmer, Water Views and Parking!
There are 23 vacation rentals with private pools near Hillsmere. Top-rated homes that have access to a swimming pool include:
- Spacious Luxe USNA Home - Pool, Hot Tub, Grill
- Oasis by the Bay - Waterfront Heated Pool Hot Tub!
- Spacious home with an outdoor pool, screened porch, washer/dryer & central AC
- Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
If you are looking for a family-friendly vacation home in Hillsmere, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Hillsmere:
Currently, the total number of properties listed in 2026 is over 847 in the Hillsmere area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Hillsmere.