Hillsmere Shores Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Hillsmere Shores vacation rentals

Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ￥24,928
￥80,964 total
includes taxes & fees
Feb 9 - Feb 10
Annapolis Retreat - 7 mins from downtown Annapolis!
Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is ￥27,019
￥76,021 total
includes taxes & fees
Feb 9 - Feb 10
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Terrace/patio

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed the stay"
United States
Kedra B.
The price is ￥20,577
￥57,417 total
includes taxes & fees
Feb 9 - Feb 10
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Fridge, microwave, oven, stovetop

Annapolis Boat Life - Overnight Stays

Annapolis Boat Life - Overnight Stays
ANNAPOLIS
10.0 out of 10, Exceptional, (1 review)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
The price is ￥33,016
￥41,000 total
includes taxes & fees
Mar 10 - Mar 11
Annapolis Boat Life - Overnight Stays
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is ￥15,070
￥43,728 total
includes taxes & fees
Feb 18 - Feb 19
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is ￥16,131
￥45,097 total
includes taxes & fees
Feb 17 - Feb 18
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

Top Location | Free Breakfast + Fitness Center

Top Location | Free Breakfast + Fitness Center
Lanham
10.0 out of 10, Exceptional, (1 review)
"Very nice!"
United States
Kerry B.
The price is ￥19,456
￥25,528 total
includes taxes & fees
Feb 8 - Feb 9
Top Location | Free Breakfast + Fitness Center
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is ￥32,453
￥64,878 total
includes taxes & fees
Feb 8 - Feb 9
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop

Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is ￥19,598
￥61,305 total
includes taxes & fees
Feb 9 - Feb 10
Luxury Pool Loft sleeps 4
Smart TV

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is ￥23,987
￥68,989 total
includes taxes & fees
Feb 8 - Feb 9
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Interior

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (36 reviews)
"This house was perfect for my husband and I, plus two daughters! We loved the location and how clean the unit was. The beds were comfortable and there were plenty of towels and all the things we needed for our weekend. We will definitely stay here again!"
United States
Emily B.
The price is ￥19,754
￥50,044 total
includes taxes & fees
Feb 11 - Feb 12
Large 2 bedroom house with private parking in a nice neighborhood
Smart TV, fireplace, foosball, table tennis

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Outdoor spa tub

London Towne Bungalow w/Loft - Walk to the Beach!

London Towne Bungalow w/Loft - Walk to the Beach!
Edgewater
8.8 out of 10, Excellent, (3 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is ￥21,792
￥74,530 total
includes taxes & fees
Feb 10 - Feb 11
London Towne Bungalow w/Loft - Walk to the Beach!
Beach

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is ￥35,276
￥56,121 total
includes taxes & fees
Feb 8 - Feb 9
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Outdoor dining

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is ￥18,114
￥67,097 total
includes taxes & fees
Feb 11 - Feb 12
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is ￥26,339
￥33,228 total
includes taxes & fees
Mar 2 - Mar 3
Sailboat Experience in Annapolis
Beach nearby, sun loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is ￥34,570
￥80,875 total
includes taxes & fees
Feb 9 - Feb 10
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Marina

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Edgewater
The price is ￥338,645
￥492,042 total
includes taxes & fees
Feb 8 - Feb 9
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Dining

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is ￥39,195
￥65,810 total
includes taxes & fees
Feb 9 - Feb 10
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
8.6 out of 10, Excellent, (8 reviews)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
United States
Jeffrey S.
The price is ￥17,121
￥55,184 total
includes taxes & fees
Feb 9 - Feb 10
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillsmere Shores Hotel Reviews

Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"Yes"
Samir 3-night trip
Posted 2 days ago
Comfort Inn Largo-Washington DC East

Find out more about Hillsmere Shores

Search for holiday rentals in Hillsmere Shores on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsmere Shores using one of the methods below:

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Look no further and take a look at our great range of rental properties in Hillsmere Shores!

Frequently asked questions

Can I find a vacation rental in Hillsmere Shores?

Yes, there are vacation rentals near top attractions in Hillsmere Shores, or you can choose a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Hillsmere Shores?

The Blue Crab Beach House - Free beach passes : Visitors like this Hillsmere Shores vacation home rental. It is located near the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a private yard and a selection of games.

How many vacation rentals are there in Hillsmere Shores?

Expedia has 11 vacation rentals for your stay in Hillsmere Shores.

What’s there to see and do in Hillsmere Shores?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Maryland Quiet Waters Park. In the larger area, you’ll find Kunta Kinte–Alex Haley Memorial and Annapolis Landing Marina.

What’s a vacation rental in Hillsmere Shores like?

Vacation rentals are private accommodations you can book for a couple days or more in Hillsmere Shores. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.