Vacation rentals in Skidmore

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Top-rated vacation rentals in Skidmore

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Guest favorite

Cottage in Annapolis

4.96 out of 5 average rating, 332 reviews

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Dec 13 – 20

G$40,569 GYD per night

Guest favorite

Guest suite in Arnold

4.96 out of 5 average rating, 562 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 6 – 13

G$23,399 GYD per night

Guest favorite

Cottage in Annapolis

4.97 out of 5 average rating, 114 reviews

Waterfront farm retreat for vacation & telework

Stay on 125-acre Hollywood Farm in a beautiful and quiet home surrounded by water and woods. Our airy, mid-century renovated cottage feels like a sanctuary, tucked away on a peninsula on one of the largest tracts of conservation land in Maryland. This cozy, light-filled space is small but spacious, allowing you to work peacefully from home with a full desk and excellent high-speed internet access. Plus, there's a dock, kayaks, and lots of outdoor space for children and pets to run around in.

Mar 21 – 28

G$68,439 GYD per night

Guest favorite

Cottage in Annapolis

4.94 out of 5 average rating, 312 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!

Aug 3 – 10

G$37,210 GYD per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 205 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.

Oct 28 – Nov 4

G$20,453 GYD 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 9 – 16

G$25,321 GYD per night

Guest favorite

Home in Annapolis

4.99 out of 5 average rating, 197 reviews

Cape St Claire waterfront getaway

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

Nov 13 – 20

G$30,047 GYD 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

G$26,400 GYD per night

Guest favorite

Guest suite in Arnold

4.94 out of 5 average rating, 114 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Yes, the hot tub IS open! 24/7/365 :-) Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Jul 30 – Aug 6

G$40,665 GYD per night

Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 104 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Oct 23 – 30

G$80,972 GYD per night

Guest favorite

Guesthouse in Grasonville

4.9 out of 5 average rating, 203 reviews

Eastern Shore Charm on Winchester Creek

My place is close to restaurants and dining and great views. You’ll love my place because of the comfy bed, the coziness, and the views. My place is good for couples, solo adventurers, and business travelers; sorry no kids. Need at least three days notice to book guest house, I like to be here when you arrive, thus schedule my social activities around bookings.

Aug 12 – 19

G$27,502 GYD per night

Guest favorite

Guest suite in Arnold

4.84 out of 5 average rating, 496 reviews

Sunny Spot Suite, Serene, Annapolis, Naval Academy

Clean, bright, private and spacious guest suite, downstairs in my home. The space is a living room, bedroom and bath. Separate entrance, complete privacy and isolation. The bedroom is dark and quiet. Disinfected and safe. Both rooms have a separate access to the bathroom. There is a lovely, lush view out the back. Self check-in.

Aug 19 – 26

G$24,528 GYD per night