Stay well, then step out and discover Hillsmere.
Best Stays by Sonder
Hillsmere
Find places to stay in Hillsmere. Choose from apartment-style stays and boutique hotels for weekend breaks, business trips, and longer city stays.
Travelers
Popular stays in Hillsmere
Start where you want to be in Hillsmere. Then compare space, amenities and style.
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Close to everything worth your time.
Stay genuinely central in Hillsmere when you want dinner, sights, and the best neighborhoods within an easy walk, without sorting through places too far from the reason you came.
Sonder hasn't arrived in Hillsmere yet. You may like these stays from trusted partners
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Parking
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Pool
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Balcony/Terrace
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Kitchen
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Breakfast
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Parking
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Balcony/Terrace
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Air Conditioner
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Pool
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Ocean View
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Balcony/Terrace
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Parking
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Pool
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Kitchen
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Air Conditioner
Hillsmere answers before you book.
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:
- Prime Eastport Location - Waterfront Condo w Pool & Parking
- Waterfront 2-Bedroom Condo on Spa Creek
- Historic Suite 2 Blocks from Main St with On-Site Parking & Dog-Friendly
- Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard
- Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
- Dean Street's Lower Deck House!
- Waterfront Suite with Views of Annapolis from Prime Eastport Location
- Prime Spot Stay–Simple Comfort, Perfect Location
- Maryland Inn 2 Double Beds | Historic Inns | 0.3 Mi to Naval Academy
- Walk To Main St & City Dock from Historic Downtown Dog-Friendly Apartment
There are 26 vacation rentals with private pools near Hillsmere. Top-rated homes that have access to a swimming pool include:
- 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.
- Poolside Annapolis Retreat for Mid-Term Stays!
- Spacious Luxe USNA Home - Pool, Hot Tub, Grill
- Oasis by the Bay - Waterfront Heated Pool Hot Tub!
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 34 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.