Hillsmere Shores Vacation Rentals

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Our top choices for Hillsmere Shores vacation rentals

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
$425 nightly
The price is $485
May 24 - May 25
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$508 nightly
The price is $579
Jun 8 - Jun 9
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
$495 nightly
The price is $564
May 26 - May 27
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
$339 nightly
The price is $359
May 20 - May 21
Total with taxes and fees
40' Bristol sailboat with spectacular views

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
9.6 out of 10, Exceptional, (10 reviews)
"Great place!"
United States
Chris A.
$382 nightly
The price is $435
Jun 3 - Jun 4
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

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)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
$395 nightly
The price is $419
May 20 - May 21
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great response time, the place is quite, house is huge and a lot of sleeping places."
United States
Luccas C.
$312 nightly
The price is $331
May 25 - May 26
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
$295 nightly
The price is $326
May 20 - May 21
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes

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, (44 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
$332 nightly
The price is $352
Jun 1 - Jun 2
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
$343 nightly
The price is $364
Jun 3 - Jun 4
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor

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, (40 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
$278 nightly
The price is $317
Jun 7 - Jun 8
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.6 out of 10, Excellent, (11 reviews)
"Jordan was a great host and communicated in a timely and professional manner. Outdoor space and pool were lovely for the hot sunny weekend. "
United States
Ellie F.
$172 nightly
The price is $196
May 20 - May 21
Total with taxes and fees
Secluded Tiny Pool House -Private Pool -Self Check in

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (54 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$258 nightly
The price is $273
May 25 - May 26
Total with taxes and fees
BAYSIDE BUNGALOW

Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (15 reviews)
"I’m late on this review but I still remember my stay a few weeks ago. The place was great and extremely welcoming. We had a wonderful time staying here!"
United States
MAD J.
$92 nightly
The price is $105
May 31 - Jun 1
Total with taxes and fees
Lower Level Loft - Adorable Studio Apt. Near BWI

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (3 reviews)
$524 nightly
The price is $533
May 26 - May 27
Total with taxes and fees
Sunset Cottage - West River Access and Views!

Cute, Cozy 2-bedroom house in near Annapolis with water access

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (7 reviews)
$203 nightly
The price is $231
May 25 - May 26
Total with taxes and fees
Cute, Cozy 2-bedroom house in near Annapolis with water access

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
$379 nightly
The price is $433
May 20 - May 21
Total with taxes and fees
3-Bedroom Beach Home w/ Backyard

Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
$407 nightly
The price is $464
Jun 4 - Jun 5
Total with taxes and fees
Idyllic Pasadena Retreat With Garden + Hot Tub!

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
9.6 out of 10, Exceptional, (14 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$601 nightly
The price is $685
Jun 2 - Jun 3
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
$475 nightly
The price is $538
May 25 - May 26
Total with taxes and fees
Cute bungalow blocks to Stadium
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

Find out more about Hillsmere Shores

Everything you need to know about Hillsmere Shores vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsmere Shores vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillsmere Shores vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillsmere Shores vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsmere Shores. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Hillsmere Shores in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $352 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Hillsmere Shores rentals

At Expedia, we put the best Hillsmere Shores vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Hillsmere Shores rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillsmere Shores vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillsmere Shores. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

NEW! Charming Farm House in Historic Kent Island : Visitors like this Hillsmere Shores vacation home rental. It is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Hillsmere Shores?

Expedia has 9 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 Carrs Beach 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.