Hillsmere Shores Vacation Rentals

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Hillsmere Shores

Interior
Upscale Condo in Annapolis

Condo in Historic District

10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
$533 nightly
The price is $608
Dec 4 - Dec 5
Total with taxes and fees
Upscale Condo in Annapolis
Smart TV, fireplace, books, printers
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Cottage in Stevensville

2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$802 nightly
The price is $885
Dec 1 - Dec 2
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Vacation Home in Grasonville

9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$395 nightly
The price is $419
Dec 1 - Dec 2
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Vacation Home in Rock Hall

2.5 star property
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
$257 nightly
The price is $272
Nov 30 - Dec 1
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Vacation Home in North Beach

10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
$297 nightly
The price is $328
Dec 1 - Dec 2
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Vacation Home in Stevensville

9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
$251 nightly
The price is $266
Nov 30 - Dec 1
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$272 nightly
The price is $288
Nov 30 - Dec 1
Total with taxes and fees
BAYSIDE BUNGALOW
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in Annapolis

10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
$484 nightly
The price is $551
Dec 2 - Dec 3
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Cottage in North Beach

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
$261 nightly
The price is $277
Nov 30 - Dec 1
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$579 nightly
The price is $660
Dec 1 - Dec 2
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Vacation Home in Shady Side

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$374 nightly
The price is $426
Nov 29 - Nov 30
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Property grounds
New! Stylish downtown home w/awesome outdoor area!

Vacation Home in Stevensville

9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
$502 nightly
The price is $532
Dec 25 - Dec 26
Total with taxes and fees
New! Stylish downtown home w/awesome outdoor area!
TV, fireplace, offices
Annapolis Baystone House

Vacation Home in Cape Saint Claire

10.0 out of 10, Exceptional, (3)
"This was a beautiful property and I would stay here again if we travel back to the area."
United States
Katherine D V.
$662 nightly
The price is $755
Dec 1 - Dec 2
Total with taxes and fees
Annapolis Baystone House
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in Stevensville

9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$246 nightly
The price is $261
Dec 2 - Dec 3
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Fridge, microwave, oven, stovetop
Edgewater's Shelby on the Bay

Vacation Home in Edgewater

9.6 out of 10, Exceptional, (8)
"what a special place! we were a group of 10 and found the house perfect for dinners, chatting around the outdoor fire and wonderful, comfy beds. The view from the house is beautiful! The kitchen could use a dish rack and a few more sharp knives, but that was just a small issue."
United States
Betsy C.
$722 nightly
The price is $823
Nov 30 - Dec 1
Total with taxes and fees
Edgewater's Shelby on the Bay
Interior
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly

Vacation Home in Cape Saint Claire

10.0 out of 10, Exceptional, (29)
"We only had a short stay but the communication with Justin was extremely quick and responsive - very clear and a great host. The property was really clean, welcoming and perfect for our short break. "
United States
Lee B.
$726 nightly
The price is $827
Dec 2 - Dec 3
Total with taxes and fees
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly
Beach nearby, sun loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Vacation Home in North Beach

10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$419 nightly
The price is $462
Dec 1 - Dec 2
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Marina
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Houseboat in Pasadena

$372 nightly
The price is $424
Nov 30 - Dec 1
Total with taxes and fees
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Apartment in Annapolis

10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Dec 1 - Dec 2
Total with taxes and fees
Waterfront Oasis of Annapolis Star
1 bedroom, desk, free WiFi, bed sheets
Lower Level Loft - Adorable Studio Apt. Near BWI

Vacation Home in South Gate

9.4 out of 10, Exceptional, (13)
"This was great for our stay. Nice place to come back to at the end of the day. It’s in a quiet neighborhood and being a lower level there is no traffic noise either. Great communication with the host and the description of the listing is accurate. Enjoy!"
United States
Jack B.
$111 nightly
The price is $127
Nov 30 - Dec 1
Total with taxes and fees
Lower Level Loft - Adorable Studio Apt. Near BWI
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean, friendly staff. Restaurant/ bar food was excellent and staff in the restaurant/ bar were fun and accommodating!"
Mary 2-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis

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 $125 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.

Explore a world of travel with Expedia

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?

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!: Visitors like this Hillsmere Shores vacation home rental. It is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Hillsmere Shores?

Expedia has 14 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.