Best Vacation Homes in Hillsmere
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $660/Night
For 7 Nights US $4,623
1528.48 ft²
8 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Pet Friendly
- Parking
- Internet
US $538/Night
For 7 Nights US $3,766
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $255/Night
For 7 Nights US $1,786
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $622/Night
For 7 Nights US $4,351
5597.23 ft²
18 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Pool
US $955/Night
For 7 Nights US $6,682
2800 ft²
8 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $546/Night
For 7 Nights US $3,822
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $718/Night
For 7 Nights US $5,029
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Spa
- Fireplace/Heating
US $1,247/Night
For 7 Nights US $8,731
Hillsmere Luxury Rentals
12 Guests
6 Bedrooms
6 Bathrooms
Ocean View
Boat Rental
- Oceanfront
- Ocean View
- View
US $3,085/Night
For 7 Nights US $21,594
2900 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $2,879/Night
For 7 Nights US $20,150
12 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pet Friendly
US $2,874/Night
For 7 Nights US $20,121
6500 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,619/Night
For 7 Nights US $18,334
3000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $2,257/Night
For 7 Nights US $15,800
3498 ft²
15 Guests
6 Bedrooms
6 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $2,126/Night
For 7 Nights US $14,882
4100 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $2,075/Night
For 7 Nights US $14,526
4164 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $2,075/Night
For 7 Nights US $14,522
Hillsmere Pet Friendly Vacation Rentals
2786 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,203/Night
For 7 Nights US $8,422
2335.77 ft²
7 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $664/Night
For 7 Nights US $4,645
2400 ft²
13 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $910/Night
For 7 Nights US $6,368
1200 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $495/Night
For 7 Nights US $3,468
1485.42 ft²
10 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $596/Night
For 7 Nights US $4,172
2400 ft²
8 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $714/Night
For 7 Nights US $4,997
1155 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $690/Night
For 7 Nights US $4,828
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $450/Night
For 7 Nights US $3,152
Hillsmere Large Vacation Homes
5922 ft²
14 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $1,864/Night
For 7 Nights US $13,051
US $126/Night
For 7 Nights US $882
3000 ft²
14 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $896/Night
For 7 Nights US $6,272
1250 ft²
10 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $527/Night
For 7 Nights US $3,691
US $419/Night
For 7 Nights US $2,933
1000 ft²
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $599/Night
For 7 Nights US $4,190
1100 ft²
12 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $683/Night
For 7 Nights US $4,780
1850 ft²
11 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $409/Night
For 7 Nights US $2,860
Why Choose Rent By Owner for your Hillsmere Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Hillsmere Vacation Rentals
Where are the best neighborhoods to stay in Hillsmere?
When exploring neighborhoods to stay in Hillsmere, Annapolis, Maryland, you’ll find a charming and scenic area perfect for a relaxing getaway. Located close to the water and surrounded by natural beauty, this neighborhood offers an ideal setting for enjoying peaceful mornings and picturesque sunsets. The community’s convenient location provides easy access to nearby attractions and amenities, making it a great choice for those seeking comfort and convenience. Whether you're looking for serene waterfront views or a welcoming neighborhood atmosphere, Hillsmere in Annapolis offers an excellent base for your Maryland vacation experience.
Hunt Meadows
Located within easy reach of the region's scenic waterfronts, Hunt Meadows offers a peaceful setting perfect for relaxing getaways. Here, you can enjoy comfortable vacation rentals that provide convenient access to Annapolis' charming local attractions.
View 825+ Rentals in Hunt MeadowsBest Times to Visit Hillsmere
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this charming area ensures you enjoy its scenic beauty and tranquil atmosphere at their best, making your stay in Hillsmere, Annapolis, Maryland, a truly memorable experience.
Peak Season Highlights
Late Spring to Early Summer (May - June)
During this time, the region experiences warm weather and longer daylight hours, making it ideal for outdoor activities and exploring the area’s scenic beauty.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Early Fall (September - October)
This period offers mild temperatures and vibrant fall foliage, providing a perfect backdrop for enjoying your stay in this destination’s charming surroundings.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F
Off-Season Highlights
Mid Winter (January - February)
During the colder months, the area sees fewer visitors, offering a peaceful retreat where you can enjoy a more relaxed and uncrowded environment.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
Late Fall (November - December)
As the region transitions into winter, you can take advantage of lower rates and quiet streets, ideal for a cozy getaway or off-season exploration.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Hillsmere
How to Book Your Hillsmere Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Hillsmere
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for meals with a view of the water.
- Relax on private patios or decks equipped with comfortable seating.
- Take advantage of waterfront access, including private docks or piers.
- Make use of well-maintained gardens and landscaped outdoor spaces.
- Utilize outdoor grilling stations for barbecues and cookouts.
- Participate in water-based activities like kayaking or paddleboarding directly from the property.
- Benefit from scenic outdoor loungers ideal for soaking up the sun in this region's welcoming climate.
Top Attractions Around Hillsmere
What attractions are nearby?
Within this charming area, you can enjoy a variety of outdoor activities such as boating, kayaking, and fishing, all just moments from your comfortable stay in Hillsmere, Annapolis, Maryland.
Family Activities
- Hillsmere Beach Park: Enjoy a relaxing day on the sandy shores with your family at this popular beach spot in Annapolis, offering calm waters ideal for kids.
- Severn River Water Activities: Engage in kayaking, paddleboarding, or boating along the scenic river that provides fun-filled adventures suitable for all ages.
- Quiet Waters Park: Explore this expansive park featuring picnic areas, nature trails, and interactive playgrounds that make it perfect for family outings in the region.
- Historic Annapolis Tour: Take a family-friendly stroll through the historic district to discover charming architecture and waterfront views that reflect the area's rich maritime heritage.
Adult Activities
- Boating and Sailing Tours: Explore the scenic waterways surrounding this destination by booking a private boat or sailing tour to enjoy the region’s beautiful maritime landscape.
- Golfing: Tee off at local golf courses where you can indulge in a relaxing round and take in the picturesque views of the area’s lush greenery.
- Fine Dining Experiences: Savor the region's culinary delights at upscale restaurants offering fresh seafood and regional cuisine, perfect for an adult night out.
- Wine Tasting and Vineyard Visits: Discover nearby vineyards and enjoy tastings of Maryland’s finest wines while taking in the tranquil countryside setting.
Other Places to Stay in Hillsmere, MD
Hunt Meadows
Maryland Quiet Waters Park
Hillsmere Shores
Hillsmere Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Waterways: Take advantage of the nearby Chesapeake Bay by enjoying kayaking or boating to experience the region’s scenic beauty firsthand.
- Visit Neighborhood Parks: Relax and unwind at local parks that offer lush green spaces, perfect for picnics or a peaceful walk amidst the natural surroundings.
- Discover Culinary Delights: Savor fresh seafood and regional cuisine at dining establishments that showcase the area’s maritime heritage.
- Plan Excursions to Nearby Attractions: Use your stay as a base to explore other popular destinations in Annapolis and beyond for a well-rounded vacation experience.
Transportation Options
- Car Rentals: Renting a vehicle here allows you to explore the scenic region and easily access local attractions from your vacation rental in Hillsmere.
- Public Transportation: The area is served by local bus services that connect you to Annapolis, making it convenient to travel without a car during your stay.
- Taxis and Rideshare Services: This destination has reliable taxis and rideshare options, providing a flexible way to get around without the hassle of parking.
- Boating and Water Transit: Given its proximity to the water, exploring via boat or water taxi offers a scenic and relaxing transportation alternative within the region.
Local Customs Options
- Waterfront Boating Etiquette: Locals take pride in their maritime traditions, so respectful behavior on boats and docks is highly valued here.
- Crab Feast Traditions: Participating in casual crab feasts is a cherished activity where sharing local steamed crabs reflects the community's friendly spirit.
- Historical Preservation: Respect for historic sites and landmarks is important, as preserving the area's rich history is a priority for residents.
- Community Events: Attending neighborhood gatherings and festivals fosters a sense of camaraderie and appreciation for this destination’s local customs.
Hillsmere Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Hillsmere?
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.
- Your Annapolis Adventure Starts Here!
- 421 Irie: Simply Charming 2 Story COTTAGE! Private Pool! 1 Off Street Parking!
2. How many vacation rentals have private pools in Hillsmere?
There are 26 vacation rentals with private pools near Hillsmere. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Hillsmere are best for families?
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:
4. How many Rentbyowner vacation rentals are available in Hillsmere?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 853 in the Hillsmere area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Hillsmere.
5. What is the cancellation policy for vacation rentals in Hillsmere near Annapolis?
Cancellation policies vary by listing, so it’s important to review the specific terms on the property’s page or contact the owner directly to understand any applicable fees or restrictions before booking.
6. Are there any additional fees or charges I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or security deposits are typically specified in the listing details. Be sure to read the full description or reach out to the host for clarification.
7. How do I find the most suitable vacation rental that meets my needs in this area?
Utilize the search filters on the website to select your preferred dates, amenities, and price range, and review the property descriptions carefully to ensure they match your travel requirements.
8. What should I know about the check-in and check-out process for vacation rentals in Hillsmere?
Check-in and check-out procedures are outlined in each listing, with some offering flexible times. Contact the owner ahead of time if you need special arrangements or have questions about accessing the property.
9. Is it safe to stay in a vacation rental here, and what safety features are usually included?
Safety features can include secure locks, smoke detectors, and first aid kits. For specific safety measures, review the listing details or communicate directly with the property owner to ensure your peace of mind during your stay.
Hillsmere Top Rated Vacation Rentals
750 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $449/Night
For 7 Nights US $3,146
1100 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $656/Night
For 7 Nights US $4,589
1001 ft²
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $519/Night
For 7 Nights US $3,630
1200 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $333/Night
For 7 Nights US $2,330
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $534/Night
For 7 Nights US $3,739
4000 ft²
14 Guests
7 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,902/Night
For 7 Nights US $13,315
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Private Pool
- Fireplace/Heating
- Pool
US $392/Night
For 7 Nights US $2,744
1950 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $733/Night
For 7 Nights US $5,131
