Vacation rentals in Sherwood Forest

4.96 out of 5 average rating, 408 reviews

Cottage in Annapolis

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.

4.92 out of 5 average rating, 48 reviews

Apartment in Annapolis

Tranquil apartment in the woods

Entire lower level of home converted to in-law suite with over 800 Sqft of space in 2 separate rooms. Private entrance, full size bath, kitchenette, 2 large screen TVs, premium cable service (including Netflix and Hulu) and ample seating. Suite contains a queen size bed and 2 sleeper sofas each with comfort foam mattress. The apartment is completely stocked with items you might need to make you visit enjoyable and hassle free. All towels and linens included. Check my discounts for longer stays.

4.96 out of 5 average rating, 671 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!

4.94 out of 5 average rating, 176 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. 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.

4.93 out of 5 average rating, 14 reviews

Home in Crownsville

Welcome to Heron House! Annapolis Waterfront Oasis

Heron House sits on the end of a pristine point surrounded by water everywhere you look. This enchanting waterfront retreat offers the perfect blend of tranquil charm and modern comfort and has been newly furnished and remodeled. Take in the spectacular views of the Severn River on the large deck with lounge seating and dining. Only 20 minutes by boat or by car to Annapolis’ City Dock, you can enjoy charming shops, historical tours, waterfront dining, and the Naval Academy. Bring your boat!

4.88 out of 5 average rating, 136 reviews

The Oasis - Cozy Comfort Close to Annapolis & USNA

Private first-floor guest apartment, a quiet retreat in a lovely residential neighborhood 7.5 miles to downtown Annapolis & USNA. Two bedrooms, living room, mini sit-in kitchen, bathroom, and laundry room. It’s ideal for travelers who want privacy, and a little more space than the usual stay. Sip your morning coffee in the gazebo and unwind after day trips fireside on the comfy sectional. The kitchen is ideal for enjoying light cooking or take outs. Comfy queen sized beds with crisp linens.

4.9 out of 5 average rating, 290 reviews

Guesthouse in Annapolis

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.

4.96 out of 5 average rating, 183 reviews

Guesthouse in Annapolis

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.

Guesthouse in Glen Burnie

4.93 out of 5 average rating, 344 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

4.99 out of 5 average rating, 136 reviews

Guesthouse in Annapolis

Garden View, a spacious 1 bedroom with loft.

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

5 out of 5 average rating, 28 reviews

Home in Annapolis

CJ's Cottage

Welcome to your perfect retreat, just 8 minutes from the lively scene of downtown Annapolis! This charming cottage offers a blend of cozy, traditional charm and modern comforts. The property is situated in a peaceful and private location with amenities that make this home the ideal spot for casual gatherings or simply relaxing with a good book and a glass of wine.

4.98 out of 5 average rating, 115 reviews

Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

Begin your mornings with wraparound views from the queen bed or coffee on the screened porch, with the same water views. "This cottage is a gem! Beautiful location, comfortable lodging, and a helpful host. It was perfect for two people. We can’t wait to return!" (March, 2025)

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Other great vacation rentals in Sherwood Forest

4.85 out of 5 average rating, 548 reviews

Sunny Spot Suite, Serene, Annapolis, Naval Academy

LindsayRating, 5 stars6 months ago

Sharon’s place was just as described. It was a convenient home base close to our family that we were visiting. We were very happy that our dogs were able to join us. There are a decent amount of steps down to the suite that we had to assist our senior pups with. The suite was clean and had a basic kitchen set up good for coffee in the morning or reheating take out. The location was very convenient to all local things to do. We were very happy with our stay.

5 out of 5 average rating, 8 reviews

Cozy & Modern Upper Level Suite

DebraRating, 5 stars1 week ago

The house is in a nice quite neighborhood. The check-in was easy with the detailed instructions on how to unlock the door. The house was spotless! It is very modern and beautiful.

Private room in Annapolis

4.96 out of 5 average rating, 336 reviews

Cape Cod Charm close to USNA & Annapolis - Room 2

JoeRating, 5 stars1 week ago

Beautifully decorated space, super clean, great location, and wonderful stay overall.

Apartment in Davidsonville

5 out of 5 average rating, 53 reviews

Aspen Woods

Gina MichelleRating, 5 stars2 weeks ago

I have nothing but good things to say about Donna and Ken. When we arrived, it was pouring rain. We had a long trailer with us and we needed to park it. Ken already had the doors open for us and helped my husband get the trailer parked in the rain. Then the next morning, he helped my husband get it backed out. The garage apartment was perfect. It was clean and felt like home. I absolutely love their place. It has everything that you need while you are there. It definitely is home away from home. The area that it is in is very nice. They have several nice restaurants. We plan on coming back in the future but without the trailer. Donna and Ken are wonderful host. Thank you so much for loaning your place out for others to enjoy.

Guest suite in Severna Park

4.98 out of 5 average rating, 58 reviews

Waterfront Apt Near Annapolis -Boat Slip available

JanRating, 5 stars4 weeks ago

Tom responded quickly, accommodated us on short notice and also was very helpful with recommendations in the area. The space matched my expectations perfectly, very comfortable, clean, and relaxing with beautiful landscaping and waterfront, with great attention to detail in furnishings, linens and extras. There is even a water cooler with cold and hot filtered water. I'm sad we did not get to stay long enough to enjoy the water recreation options, but hope to return for a longer stay. Highly recommend!

4.95 out of 5 average rating, 95 reviews

Guest suite in Annapolis

Annapolis Garden Suite

StacyRating, 5 stars5 days ago

Thank you for sharing your beautiful home and charger lol with us ! We will book again

4.77 out of 5 average rating, 26 reviews

Cottage in Severna Park

Colorful Round Bay Cottage

KatherineRating, 5 stars2 days ago

Jennifer’s house is one of the best AirB&B’s we have ever stayed in. The cottage was beautifully furnished, remarkably clean, and in a great location. It was spacious and comfortable. The primary bathroom has an incredibly shower. We would definitely like to return one day!