Vacation rentals in Annapolis Yacht Basin

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Top-rated vacation rentals in Annapolis Yacht Basin

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Guest favorite

Guest suite in Arnold

4.96 out of 5 average rating, 565 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Jul 14 – 21

$98 per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 206 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.

Jan 10 – 17

$85 per night

Guest favorite

Boat in Annapolis

4.94 out of 5 average rating, 351 reviews

Stay aboard the S/V MY STUDIO on Annapolis Harbor

Discover life aboard a comfortably equipped sailing yacht. Great for couples on a weekend getaway, and child friendly for families looking to include their little pirates. Hands down this is a wonderful way to visit Historic Annapolis and Naval Academy. We love the opportunity to share our boat, and help create a memorable vacation. Weather permitting, Private Sailing Cruises can be arranged during your stay for an additional charge. Cheers, and I look forward to welcoming you aboard.

Sep 11 – 18

$173 per night

Guest favorite

Guesthouse in Annapolis

4.87 out of 5 average rating, 312 reviews

Chesapeake Birdhouse Studio

Private, clean, cozy studio in the heart of Eastport, Annapolis. Quiet, separate, retreat space. Walk 1 block to restaurants and bars in Eastport, hop on the water taxi and you are in the heart of Downtown Annapolis, USNA, and historic areas of Annapolis in minutes. This is an Ideal location for the sailing community or anyone visiting our beautiful city. Free street parking available. You could park your car and never have to move it through out your stay. Walk, bike or water taxi.

Sep 25 – Oct 2

$105 per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 155 reviews

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Aug 12 – 19

$123 per night

Guest favorite

Apartment in Crownsville

4.98 out of 5 average rating, 163 reviews

“River Sweet" Private Apartment

River Sweet has everything you need for a fun and relaxing getaway. Cozy and clean, River Sweet provides all the comforts of home, including your own driveway and entrance. You'll delight in privacy while enjoying a safe, waterfront neighborhood. A local mini mart and restaurant are close by. And, you are centrally located between Annapolis, Baltimore and Washington for fun excursions! Please let us know if you need a long-term stay. We would be happy to accommodate you.

Aug 16 – 23

$91 per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Recently renovated (Feb. 2021) one bedroom Guesthouse with fully equipped kitchen, new king sized bed with premium Saatva mattress, full bathroom and large living room in a quiet neighborhood near the South River, Quiet Waters Park and downtown historic Annapolis. We employ professional cleaning services between each guest stay.

Jul 26 – Aug 2

$109 per night

Guest favorite

Home in Annapolis

4.96 out of 5 average rating, 109 reviews

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit.

Apr 15 – 22

$106 per night

Guest favorite

Guest suite in Annapolis

4.97 out of 5 average rating, 163 reviews

Private 2B Apt--less than 1 mi to Downtown

A fully finished modern basement apartment with separate/private entry, in charming Eastport less than a mile from downtown Annapolis. Street parking is always available at the entrance to the apartment. Easy access to nearby restaurants, marinas, and US Naval Academy.

Apr 3 – 10

$136 per night

Guest favorite

Loft in Annapolis

4.91 out of 5 average rating, 920 reviews

Step Out to Main Street From a Chic Loft

This loft apartment features an exquisite industrial-chic aesthetic where exposed brick walls and hardwood floors are accentuated by metallic textures and rustic items. Curl up with a book from the bookshelf or sink into the sofa to watch TV.

Jul 11 – 18

$135 per night

Guest favorite

Guest suite in Annapolis

4.96 out of 5 average rating, 368 reviews

Our Annapolis Penthouse

This rental is private studio above our home in the Murray Hill neighborhood of Annapolis. Walk to town, upper West St. restaurants, Academy Stadium. It has a private entrance and it's own heat /AC control. Pool privileges may be offered.

Jan 3 – 10

$95 per night