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Hillsmere Shores Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Hillsmere Shores holiday rentals

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

1. 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 HK$1,336
HK$3,786 total
includes taxes & fees
1 Nov - 2 Nov
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

2. 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.
The price is HK$1,703
HK$4,634 total
includes taxes & fees
9 Nov - 10 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (26 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is HK$516
HK$1,635 total
includes taxes & fees
12 Oct - 13 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

4. 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, (55 reviews)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is HK$923
HK$2,447 total
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is HK$625
HK$2,174 total
includes taxes & fees
14 Oct - 15 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

6. 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, (43 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is HK$1,095
HK$2,644 total
includes taxes & fees
12 Oct - 13 Oct
Large 2 bedroom house with private parking in a nice neighborhood
A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

7. Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (20 reviews)
"This was an adorable little place, perfect for my husband and I. With a few minor tweaks and upgrades, this would easily be a five star stay. I would happily stay here again. Thank you!"
United States
Deanna
The price is HK$557
HK$904 total
includes taxes & fees
12 Oct - 13 Oct
Lower Level Loft - Adorable Studio Apt. Near BWI
A bedroom with a bed, a window, a painting, and a wall-mounted air conditioner.

8. 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, (13 reviews)
"Great place!"
United States
Chris A.
The price is HK$1,236
HK$3,145 total
includes taxes & fees
22 Oct - 23 Oct
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

9. Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
The price is HK$1,749
HK$3,883 total
includes taxes & fees
18 Oct - 19 Oct
Dean Street's Lower Deck House!
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

10. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (2 reviews)
"The location of this home is stellar! Every shop and restaurant is within walking distance. The home is super clean and charming. Tastefully furnished both in style and comfort. The kitchen was fully stocked. The bathrooms are updated and beautiful. The showers are fantastic! Eric was a gem to work with!"
United States
gina w.
The price is HK$1,460
HK$4,455 total
includes taxes & fees
20 Oct - 21 Oct
Historic Row Home in Downtown Annapolis
A living room with a beige sofa, two framed floral pictures, a wooden cabinet, and a small table with a lamp.

11. Cozy 1-bedroom studio in pleasant Crofton with AC

Cozy 1-bedroom studio in pleasant Crofton with AC
Crofton
9.0 out of 10, Wonderful, (2 reviews)
"Host was very friendly and accommodating. The location is wonderful. Lots of shops and festivities nearby could not have asked for better. Her cat was also very friendly "
United States
Michaela C.
The price is HK$848
HK$1,145 total
includes taxes & fees
12 Oct - 13 Oct
Cozy 1-bedroom studio in pleasant Crofton with AC
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

12. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is HK$1,781
HK$4,768 total
includes taxes & fees
2 Nov - 3 Nov
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

13. Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is HK$1,687
HK$4,347 total
includes taxes & fees
20 Oct - 21 Oct
Upscale Condo in Annapolis w/Private Parking
A deck with outdoor furniture, a red door, and a house with windows.

14. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is HK$1,349
HK$2,969 total
includes taxes & fees
26 Oct - 27 Oct
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A living room with a dining table, two sofas, a coffee table, and a patterned rug.

15. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
10.0 out of 10, Exceptional, (1 review)
"Very cute home in great proximity to naval academy"
United States
JENNIFER E.
The price is HK$1,546
HK$4,004 total
includes taxes & fees
4 Nov - 5 Nov
Chapel Gate 3BR Steps to City Dock & Naval Academy
Stylish kitchen with open layout and island seating

16. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (8 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 HK$1,639
HK$3,970 total
includes taxes & fees
13 Oct - 14 Oct
Pool Loft Suite | Bay Access & Beach Passes
A wooden dock extending into a calm body of water with boats docked at the end.

17. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is HK$1,962
HK$3,784 total
includes taxes & fees
20 Oct - 21 Oct
Cozy 2br home w/ parking in downtown Annapolis
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

18. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is HK$1,774
HK$3,766 total
includes taxes & fees
10 Nov - 11 Nov
Sunset Cottage - West River Access and Views!
A beach with chairs and a pier in the background.

19. 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, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$1,660
HK$3,950 total
includes taxes & fees
20 Oct - 21 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Great breakfast, big rooms"
Daniel 3-night trip
Posted 1 hour ago
Sonesta ES Suites Annapolis

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:

  • View our selection of featured holiday rentals in Hillsmere Shores
  • Use the map to find apartments and other holiday homes in the Hillsmere Shores neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hillsmere Shores while they last

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

Frequently asked questions

Can I find a holiday rental in Hillsmere Shores?

Yes, there are holiday rentals close to the most popular sights in Hillsmere Shores, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Hillsmere Shores has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Hillsmere Shores is located near the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Hillsmere Shores?

Expedia has 7 holiday 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 wider area, you’ll find Bay Ridge Beach and Maryland Hall for Creative Arts.

What’s a holiday rental in Hillsmere Shores like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Hillsmere Shores. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.