Hillsmere Shores Holiday Rentals from €206: Search Short-Term Rentals

Q: 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.

Q: 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.

Q: How many holiday rentals are there in Hillsmere Shores?

Expedia has 8 holiday rentals for your stay in Hillsmere Shores.

Q: 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.

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Hillsmere Shores holiday rentals

1. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

William

includes taxes & fees

27 Aug - 28 Aug

2. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

8 Sept - 9 Sept

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

Historic District

Mary G.

includes taxes & fees

31 Aug - 1 Sept

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

Annapolis

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.

Eastport

Michaell M.

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

Edgewater

Kristin G.

includes taxes & fees

27 Aug - 28 Aug

7. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

includes taxes & fees

24 Sept - 25 Sept

8. Charming Annapolis WaterVIEW Home

Arundel on the Bay

Whitney M.

includes taxes & fees

14 Sept - 15 Sept

Coffee/tea maker, fridge, microwave, oven

9. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Historic District

Colleen W.

10. New Downtown Annapolis Condo With Free Parking

Historic District

Darby F.

includes taxes & fees

31 Aug - 1 Sept

11. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport

william c.

includes taxes & fees

27 Aug - 28 Aug

Smart TV, fireplace, table football, ping pong

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

Homewood

Dan B.

13. Londontowne Rancher | 3BR | Near Waterfront

Edgewater

"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. "

rebekah h.

includes taxes & fees

27 Aug - 28 Aug

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

Edgewater

Diane D.

includes taxes & fees

2 Sept - 3 Sept

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

Admiral Heights

Jennifer G.

includes taxes & fees

27 Aug - 28 Aug

16. Cute bungalow blocks to Stadium

Admiral Heights

Tammy L.

17. Waterfront Oasis of Annapolis Star

Annapolis

Thomas

includes taxes & fees

27 Aug - 28 Aug

18. Dean Street's Lower Deck House!

Historic District

Nathaniel R.

includes taxes & fees

31 Aug - 1 Sept

19. Secluded Cozy Cottage in Historic Downtown

Historic District

Tim G.

includes taxes & fees

27 Aug - 28 Aug

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Top Hillsmere Shores Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The location of the hotel was awesome along with our balcony view. However you should not have to pay an additional $50 per day to park your car especially since the garage up the street is Therefore the guests are getting pentalized to park at the hotel . Additionally the front desk women were rude and condescending"

St Michaels Inn

8/10 Good

"This is a typical motel. The room seemed to just have been upgraded in the past 6 months or so. Room had fresh paint, and new vinyl plank flooring. I also believe that our king bed as a newer mattress. The furniture was in good condition but the lamps seemed to be original 50's style. The bathroom still had the original tub/shower with an upgraded shower head. The toilet was most likely original too and very low; as a senor citizen it was so low that it was harder to get up. The sink and marble counter were outside of the bathroom and a nice touch although the two big mirrors must b original since they both has part of the silver coating on the back lower edge eroded by moisture. The breakfast was pitiful; waffle iron and batter machine were in place but not being used. Same for the two-section heated server that was supposed to possible have scrambled eggs and maybe sausage but they were not used either. Thus there were muffins, bangles, and serial. Still in the St. Michaels area and at the priced charged, one could not do much better."

Graduate by Hilton Annapolis

10/10 Excellent

"I arrived late following a long-distance sailboat race across the Chesapeake Bay. “Nick” was managing the front desk. He was polite, efficient, friendly, and professional. He offered me the best room the hotel had available at my price, and guaranteed I would have a good night’s rest. He was 100% correct. The room was clean and comfortable, and more importantly it was quiet. Check out was easy the next morning."

Crowne Plaza Annapolis by IHG

8/10 Good

"I wish I could give half stars because this place is really a 4.5 stars. First off this place was great, it is everything you need for a hotel. Great prices, friendly staff, very clean, very nice hotel. Why I gave it 4 stars? The coffee machine was down for our first night, the jacuzzi was down for maintenance, the wifi went for maintenance lol so it was a little much but I know you can't always control those things. Another small thing, I also wish the TV's were smart TV's and I wish the rooms came with a microwave. Overall great hotel, would stay here again."

Find out more about Hillsmere Shores

Everything you need to know about Hillsmere Shores holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsmere Shores holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillsmere Shores holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillsmere Shores holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsmere Shores holiday rentals we have selected for you start as low as €206 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hillsmere Shores rentals

At Expedia, we put the best Hillsmere Shores holiday 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 holiday.

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 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.

Room 1

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Check prices for these dates

Our top choices for Hillsmere Shores holiday rentals

1. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

2. Annapolis Retreat - 7 mins from downtown Annapolis!

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

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

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.