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Hillsmere Shores Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Hillsmere Shores vacation 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 ￥26,868
￥76,157 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥32,991
￥91,234 total
includes taxes & fees
Nov 2 - Nov 3
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
9.6 out of 10, Exceptional, (24 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 ￥10,939
￥33,524 total
includes taxes & fees
Oct 12 - Oct 13
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)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is ￥13,967
￥45,621 total
includes taxes & fees
Oct 5 - Oct 6
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 ￥16,795
￥48,760 total
includes taxes & fees
Oct 7 - Oct 8
Charming Coastal/Country Home w/3 Acres & Sauna!
A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

6. 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 ￥11,207
￥18,174 total
includes taxes & fees
Oct 6 - Oct 7
Lower Level Loft - Adorable Studio Apt. Near BWI
A modern kitchen with dark cabinets, a white countertop, and a large window.

7. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
The price is ￥14,207
￥42,356 total
includes taxes & fees
Oct 8 - Oct 9
Cass-N-Reel Luxury Houseboat
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

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, (12 reviews)
"Great place!"
United States
Chris A.
The price is ￥24,861
￥62,532 total
includes taxes & fees
Oct 28 - Oct 29
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
A living room with a beige sofa, two framed floral pictures, a wooden cabinet, and a small table with a lamp.

9. 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 ￥17,048
￥23,034 total
includes taxes & fees
Oct 8 - Oct 9
Cozy 1-bedroom studio in pleasant Crofton with AC
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

10. 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, (41 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 ￥22,020
￥53,175 total
includes taxes & fees
Oct 5 - Oct 6
Large 2 bedroom house with private parking in a nice neighborhood
A house with a yellow door and a window with a lamp outside.

11. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is ￥20,599
￥51,915 total
includes taxes & fees
Oct 8 - Oct 9
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

12. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is ￥10,893
￥48,968 total
includes taxes & fees
Oct 6 - Oct 7
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Stylish kitchen with open layout and island seating

13. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 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 ￥30,402
￥76,587 total
includes taxes & fees
Oct 5 - Oct 6
Pool Loft Suite | Bay Access & Beach Passes
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 ￥26,992
￥59,023 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

15. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is ￥45,344
￥67,863 total
includes taxes & fees
Oct 5 - Oct 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

16. 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 ￥35,832
￥94,653 total
includes taxes & fees
Oct 20 - Oct 21
Renovated Bungalow | Walk to Beach | Dog-Friendly
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

17. 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 ￥34,637
￥73,137 total
includes taxes & fees
Oct 18 - Oct 19
Dean Street's Lower Deck House!
A wooden dock extending into a calm body of water with boats docked at the end.

18. 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 ￥33,938
￥68,021 total
includes taxes & fees
Oct 20 - Oct 21
Cozy 2br home w/ parking in downtown Annapolis
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

19. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
8.0 out of 10, Very good, (1 review)
"This property was an up and down property for us. The ups: check in process was flawless; cleanliness was as good as an old house can be; and the location was superb. The downs: they say it can sleep ten. Well ten people might sleep but they can’t do much else. There are two baths and the kitchen was fine and although adequate to work with. But there are only four wine glasses and barely five people can sit at the dining room table. So if ten people sleep - they wake up and there are enough...
United States
DEAN F.
The price is ￥29,360
￥89,075 total
includes taxes & fees
Oct 5 - Oct 6
Historic Row Home in Downtown Annapolis
A modern kitchen with a central island, built-in oven, and microwave.

20. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is ￥32,675
￥83,108 total
includes taxes & fees
Oct 6 - Oct 7
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great Hotel in a very central location"
Mark 2-night trip
Posted 1 hour ago
Graduate by Hilton 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:

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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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Hillsmere Shores vacation home rental. It is located near the beach and has a fireplace, a balcony, 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Hillsmere Shores?

Expedia has 7 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 Bay Ridge Beach and Maryland Hall for Creative Arts.

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.