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Hillsmere Shores Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Hillsmere Shores holiday rentals

Marina

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$1,501
HK$3,971 total
includes taxes & fees
26 Aug - 27 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Interior

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$1,842
HK$4,815 total
includes taxes & fees
8 Sept - 9 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
Marina

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (85 reviews)
"Thank you for the stay! We loved the location."
United States
Mary G.
The price is HK$1,763
HK$3,502 total
includes taxes & fees
26 Aug - 27 Aug
Cozy 2br home w/ parking in downtown Annapolis
Living area

4. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is HK$1,931
HK$5,033 total
includes taxes & fees
26 Aug - 27 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Interior

5. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
The price is HK$2,718
HK$6,111 total
includes taxes & fees
26 Aug - 27 Aug
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Living area

6. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,897
HK$5,504 total
includes taxes & fees
26 Aug - 27 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
Beach

7. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is HK$1,898
HK$5,793 total
includes taxes & fees
26 Aug - 27 Aug
Londontowne Home | Beach | 3BR
Outdoor dining

8. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (75 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is HK$2,602
HK$5,316 total
includes taxes & fees
14 Sept - 15 Sept
Charming Annapolis WaterVIEW Home
Private kitchen

9. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is HK$2,054
HK$5,649 total
includes taxes & fees
26 Aug - 27 Aug
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Interior

10. New Downtown Annapolis Condo With Free Parking

New Downtown Annapolis Condo With Free Parking
Historic District
10.0 out of 10, Exceptional, (43 reviews)
"Beautiful property, excellent location, and had a wonderful visit to Annapolis!"
United States
Darby F.
The price is HK$1,481
HK$3,314 total
includes taxes & fees
31 Aug - 1 Sept
New Downtown Annapolis Condo With Free Parking
Private kitchen

11. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport 3 bedroom Cottage: Walk to Downtown
Eastport
10.0 out of 10, Exceptional, (1 review)
"We had a nice stay. All was fine."
United States
william c.
The price is HK$2,557
HK$5,837 total
includes taxes & fees
26 Aug - 27 Aug
Eastport 3 bedroom Cottage: Walk to Downtown
Living area

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

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is HK$1,810
HK$4,118 total
includes taxes & fees
26 Aug - 27 Aug
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Living area

13. Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
United States
rebekah h.
The price is HK$1,897
HK$5,504 total
includes taxes & fees
26 Aug - 27 Aug
Londontowne Rancher | 3BR | Near Waterfront
Private kitchen

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 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$1,638
HK$4,574 total
includes taxes & fees
2 Sept - 3 Sept
Renovated Bungalow | Walk to Beach | Dog-Friendly
Exterior

15. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (54 reviews)
"Great stay in Annapolis. The property is gorgeous. Everything you need for a great weekend in Annapolis. "
United States
Jennifer G.
The price is HK$2,997
HK$3,908 total
includes taxes & fees
27 Aug - 28 Aug
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Private kitchen

16. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 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 HK$1,622
HK$4,180 total
includes taxes & fees
30 Aug - 31 Aug
Cute bungalow blocks to Stadium
Pool

17. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,516
HK$3,087 total
includes taxes & fees
26 Aug - 27 Aug
Waterfront Oasis of Annapolis Star
Interior

18. 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$1,595
HK$3,506 total
includes taxes & fees
31 Aug - 1 Sept
Dean Street's Lower Deck House!
Marina

19. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is HK$3,526
HK$5,825 total
includes taxes & fees
26 Aug - 27 Aug
Secluded Cozy Cottage in Historic Downtown
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Gorgeous historical property that’s a must see Staff was friendly and helpful down to the valet that was so kind and welcoming Great neighborhood in walking distance of great restaurants"
Deanna 1-night trip
Posted less than an hour ago
Historic Inns of 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 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 8 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 Annapolis Landing Marina and Bay Ridge Beach.

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.