Vacation rentals in Hillsmere Shores

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Top-rated vacation rentals in Hillsmere Shores

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 122 reviews

Waterfront Chesapeake Bay Getaway Firepit & Pier!

Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from your private pier & enjoy the peace, serenity and bay breezes from your furnished deck and green space. Enjoy true nature and explore Selby Bay on the South River with our complimentary canoe! Super clean with water views from kitchen, dining, living room & enclosed porch! Situated in a quiet neighborhood within 45 minutes of DC & 15 minutes from Annapolis & the Naval Academy.

Nov 11 – 18

R6,084 ZAR per night
Guest favorite

Cottage in Annapolis

4.94 out of 5 average rating, 308 reviews

Wright’s Cottage, Pets Welcome!

We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!

Jun 27 – Jul 4

R4,065 ZAR per night
Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 202 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Nov 14 – 21

R1,856 ZAR per night

Popular amenities for Hillsmere Shores vacation rentals

Stay near Hillsmere Shores's top sights

Quiet Waters Park126 locals recommend
Annapolis Smokehouse And Tavern18 locals recommend
Grump's Cafe23 locals recommend
Rocco's Pizzeria9 locals recommend
Jack's Fortune6 locals recommend
Caliente Grill8 locals recommend

Other great vacation rentals in Hillsmere Shores

Guest favorite

Guest suite in Arnold

4.94 out of 5 average rating, 110 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Sep 3 – 10

R2,930 ZAR per night
Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Mar 18 – 25

R9,123 ZAR per night
Guest favorite

Guesthouse in Galesville

4.95 out of 5 average rating, 163 reviews

Gorgeous water view studio!

Jun 29 – Jul 6

R3,526 ZAR per night
Guest favorite

Home in Annapolis

4.99 out of 5 average rating, 195 reviews

Cape St Claire waterfront getaway

Sep 26 – Oct 3

R2,726 ZAR per night
Guest favorite

Home in Annapolis

4.95 out of 5 average rating, 39 reviews

Naptown Suite

May 1 – 8

R1,795 ZAR per night
Guest favorite

Home in Annapolis

4.88 out of 5 average rating, 24 reviews

Cute cozy rancher close to down town Annapolis

Apr 29 – May 6

R2,177 ZAR per night
Guest favorite

Apartment in Annapolis

4.93 out of 5 average rating, 30 reviews

Hillsmere Hideaway

Aug 23 – 30

R2,596 ZAR per night
Guest favorite

Guesthouse in Edgewater

5.0 out of 5 average rating, 54 reviews

1 large room efficiency in detached garage.

Nov 16 – 23

R2,164 ZAR per night
Superhost

Apartment in Annapolis

4.89 out of 5 average rating, 19 reviews

Annapolis Charmer! 2BR Bright BSMT APT 3 mi to DT

Dec 6 – 13

R2,747 ZAR per night
Guest favorite

Guesthouse in Annapolis

4.95 out of 5 average rating, 77 reviews

Private Cottage on gated estate

Apr 25 – May 2

R2,850 ZAR per night
Guest favorite

Guest suite in Riva

5.0 out of 5 average rating, 7 reviews

Cozy one bedroom appt on the water

Jul 17 – 24

R1,577 ZAR per night
Guest favorite

Guesthouse in Annapolis

4.85 out of 5 average rating, 52 reviews

Annapolis 1- bedroom Oasis by the Bay!

Jul 30 – Aug 6

R2,405 ZAR per night

Destinations to explore