Stunning Waterfront Retreat w/Pool, Private Dock & Sauna Near Downtown Annapolis | House in Annapolis

9.0 (2 Reviews) |   Pet Friendly   4 Bedrooms  4 Bathrooms  8 Guests
Hillsmere House | Stunning Waterfront Retreat w/Pool, Private Dock & Sauna Near Downtown Annapolis

4 Bedroom House in Hillsmere, Annapolis

STR000259 - Just minutes from downtown Annapolis, this stunning waterfront home offers a private, upscale retreat for up to 8 guests. Located in a quiet residential neighborhood, the property combines modern design, spacious indoor living, and beautiful outdoor spaces for a memorable stay on the water.
Inside, the home features soaring ceilings, light-filled living areas, and sweeping waterfront views. The gourmet kitchen is equipped with a six-burner stove, three dishwashers, and wine storage, and opens to a comfortable family room with easy access to the deck and pool area. A formal dining room provides an elegant setting for meals with family and friends.
The home offers 4 spacious bedrooms, each with its own en-suite bathroom. One guest bedroom is located on the main floor, ideal for those who prefer fewer stairs. Upstairs, the primary suite features vaulted ceilings, a private balcony with panoramic water views, and a spa-like bathroom with a soaking tub, shower, bidet, and Finnish sauna. Two additional upstairs guest suites offer designer bathrooms and generous closet space.
Guests will also enjoy a large recreation and TV room with a pool table, piano, treadmill, Pilates machine, free weights, and balcony access overlooking the pool and water.
Outside, the beautifully landscaped grounds are designed for relaxing and enjoying the setting. The contemporary pool is open from Memorial Day through Labor Day and is surrounded by multiple seating areas, waterfront decks, and peaceful garden spaces. A Big Green Egg, gas grill, outdoor dining area, and copper fire pit make it easy to enjoy time outdoors from morning coffee to evening gatherings.
For those who love the water, the property includes a private dock and pier, 4 kayaks, 2 paddleboards, and 2 bikes for exploring the area. Parking is available for up to 6 cars, and a full-size washer and dryer are located on the main floor for added convenience.
This home is ideal for families and small groups seeking a relaxing waterfront escape with easy access to Annapolis dining, shopping, and attractions. Please note that this property is located in a peaceful residential community and is best suited for respectful guests looking to enjoy the home and surroundings.
Important to note: This waterfront property includes a pool, dock, pier, kayaks, and paddleboards. Use of these amenities is at guests’ own risk. Children must be supervised at all times near the water and pool. There is no lifeguard or on-site supervision. No diving or jumping from the pier. Guests must use all equipment safely, inspect equipment before use, and report any damage or unsafe conditions. Use of the dock, kayaks, and paddleboards requires agreement to a separate waterfront/recreational equipment addendum before arrival.

Stunning Waterfront Retreat w/Pool, Private Dock & Sauna Near Downtown Annapolis is located in Hillsmere. Stunning Waterfront Retreat w/Pool, Private Dock & Sauna Near Downtown Annapolis provides accommodation, featuring Fireplace/Heating, Air Conditioner, Parking, among other amenities. This House features Fireplace/Heating, Air Conditioner, Parking, to make your stay a comfortable one.

Stunning Waterfront Retreat w/Pool, Private Dock & Sauna Near Downtown Annapolis has 4 Bedrooms , 4 Bathrooms, and max occupancy of 8 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Hillsmere has interesting places to visit. If you want to learn more about the House in Hillsmere, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pet Friendly
Pool
Private Pool
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Spa
Fireplace/Heating
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Hair dryer
  • Towels provided
  • 4+ bathrooms
Bedroom
  • 4 bedrooms
  • Bed sheets provided
  • Living room
Kitchen
  • Dishwasher
  • Spices
  • Stovetop
  • Refrigerator
  • Toaster
  • Microwave
  • Coffee/tea maker
  • Cookware/dishes/utensils
  • Oven
Laundry
  • Near laundromat
  • Washing machine and dryer
Parking
  • Car recommended
  • Onsite parking
Pet Friendly
  • Pet friendly
  • Welcoming dogs only
  • 1 total (up to 50 lbs per pet)
Accessibility
  • Smoke-free property
Activities
  • Marina nearby
  • Golf nearby
  • Power boating nearby
  • Sailing nearby
  • Fitness facilities nearby
  • Fishing nearby
  • Birdwatching nearby
  • Kayaking nearby
  • Wildlife and game walks nearby
Entertainment
  • Books
  • Arcade/game room
  • Pool or billiards table
  • Stereo
General
  • English
  • Near the bay
  • Near a hospital
  • On the waterfront
Guest Services
  • Iron/ironing board
Internet
  • WiFi available
Outdoors
  • Barbecue grill
  • Balcony
  • Garden
Security/Safety
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
Spa
  • Sauna
  • Private pool
  • Heated pool

Policies

Check-in
Check-in time starts at 3:00 pm contactless check-in available minimum check-in age: 25
Check-out
Check-out before 10:00 am
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
1 total (up to 50 lbs per pet) pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy
Smoking is not permitted

Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited property registration number str000259 special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

License number: STR000259

Reviews

Sanjay O.
Sep 11, 2025 01:08:02 AM
Review Score:   10
Summary: The house is very beautiful and located by water with very quaint views and very tranquil. The Neighbourhood is very well-maintained and the house is exceptionally well kept. Our check process was very smooth and the management company was responsive as well. Highly recommend this place.
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FAQ's

Is this Hillsmere house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Hillsmere house have a swimming pool?

Yes, this Hillsmere house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Hillsmere house?

Best-rates for the Hillsmere house starts from $1,258 per night with includes Air Conditioner, Parking, Pool, Bedding/Linens, Private Pool, Barbecue/Outdoor Cooking, Internet, Pet Friendly, Balcony/Terrace, Security/Safety, Wellness Facilities, Child Friendly, Kitchen, Laundry, Sports/Activities, Spa, Entertainment, Fireplace/Heating with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Hillsmere house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Hillsmere house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Hillsmere house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Hillsmere house?

Based on the information reported by the owner or manager, the Hillsmere house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Hillsmere house?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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