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Compare 533 Vacation Homes in Sherwood with updated reviews, rates, and availability.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Grill no longer works

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (87)
"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Enjoy the sunset from Long Wharf Marina across the street

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

10.0 out of 10, Exceptional, (6)
"This stay was perfect. The location was charming and safe, and the home was clean and cozy. Jennifer was a very accommodating and responsive host."
The price is SAR 657
SAR 1,473 total
includes taxes & fees
16 Dec - 17 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Bay views with kayaks, bikes, fire pit, crabbing and more
Living room with tv and gas fireplace

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (17)
"Very clean, everything as described. Awesome host, communication an A+. Would definitely stay again, if we are in the area."
Bay views with kayaks, bikes, fire pit, crabbing and more
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Exterior

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (3)
"The house was very clean and was great for our home base while visiting family in St. Michael’s. The owner was very response and friendly. The house included all basic amenities and then some! The owner really took the time and care preparing this place for guests. Downtown Cambridge is a short drive and a cute little town with shops and restaurants. We didn’t have a ton of time to explore downtown but plan to on our next stay! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Recently Renovated Annapolis Home - Conveniently Located
Single Family Home With Parking for two small or one larger vehicle.

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (56)
"This house is so cute and comfortable. Everything was perfect and better than described. It is within walking distance of some delicious restaurants. Our host was amazing and answered all questions very quickly."
Recently Renovated Annapolis Home - Conveniently Located
3 Story Stunner in Murray Hill <1 mile from USNA!

3 Story Stunner in Murray Hill <1 mile from USNA!

10.0 out of 10, Exceptional, (18)
"Very nicely renovated property in the heart of downtown Annapolis. Highly recommend for groups / families and very kid friendly. Great location to walk to all that Annapolis has to offer. "
The price is SAR 856
SAR 3,405 total
includes taxes & fees
4 Dec - 5 Dec
3 Story Stunner in Murray Hill <1 mile from USNA!
Your Annapolis Adventure Starts Here!!
Annapolis Adventure Awaits - Book Now For March 2023 Festivities!

Your Annapolis Adventure Starts Here!!

10.0 out of 10, Exceptional, (136)
"My family and I love staying here! It's clean, beautiful, spacious, and comfortable. It's home away from home. I love all the special touches--lots of cozy blankets, the beautiful decor, the comfortable beds. And, of course, it's close to anything you want to do in Annapolis or the surrounding areas. During this stay, we were able to enjoy the patio, which was especially wonderful to be able to do in November. My favorite spot is the sitting area next to the kitchen; it's a perfect place to...
Your Annapolis Adventure Starts Here!!
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Amazing Location

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (108)
"We have stayed at this property multiple times since we have a son at the Naval Academy. This place is beautiful, well appointed and comfortable. The hosts are very responsive and they go out of their way to make their guests feel extra special- we will be back. "
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Welcome to Annapolis Heron House

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (71)
"House is exceptionally clean. Hosts are very responsive to questions. House is very well supplied and convenient to most of Annapolis. House is as advertised. "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Charming Historic Townhouse Steps From USNA
Interior

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (20)
"We had the best time at this rental — it was accessible, cozy, stocked with things like good toilet paper (silly, but we noticed and appreciated!), and in an amazing location! Absolutely recommend! "
Charming Historic Townhouse Steps From USNA
Waterfront Home on the Chesapeake Bay!
Private Pier

Waterfront Home on the Chesapeake Bay!

10.0 out of 10, Exceptional, (23)
"Very nice getaway for a family reunion group of 8 while we visited our son at the USNA. Location is 35 min from US Naval academy; perfect to feel like he's really getting off the Yard. Having such a huge yard really offered lots to do (corn hole, frisbee, etc.). The incredible water views drew us all back home every night, along with the gorgeous sunsets. Had really nice weather so we took advantage of the 3 kayaks and paddled around the marina. Bikes were convenient too, as well as small...
Waterfront Home on the Chesapeake Bay!
Edgewater/Mayo Getaway!
Room

Edgewater/Mayo Getaway!

9.8 out of 10, Exceptional, (10)
"We only stayed one night but the house was perfect for our needs. The main family room/kitchen area was perfect for all of us to comfortably sit together, and the bedroom layout was great for two families (two “wings”). The hosts were super responsive and accommodating. Would just suggest two hairdryers (one in each bathroom - if there was a second, we did not see it) and shower soap. The bed in the primary bedroom was very comfortable and everything went smoothly. "
The price is SAR 762
SAR 2,052 total
includes taxes & fees
1 Dec - 2 Dec
Edgewater/Mayo Getaway!
La Maison - Stunning waterfront views with pool
Tranquil retreat on the South River - private dock

La Maison - Stunning waterfront views with pool

10.0 out of 10, Exceptional, (90)
"Gorgeous, serene and well-appointed property! It was very comfortable for our group of four women. Highly recommend for a family or friends."
La Maison - Stunning waterfront views with pool
Charming brick home with patio, WiFi, AC, & W/D - walk to everything

Charming brick home with patio, WiFi, AC, & W/D - walk to everything

8.8 out of 10, Excellent, (19)
"Loved this location as EVERYTHING is walkable - St John's college, USNA, the capitol and Main Street. One skinny parking place was appreciated and reasonable for a standard size vehicle (not super truck or SUV). Enjoyed the older character of the home and modern conveniences as well as small outdoor space that was very nicely landscaped with flowers. "
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
Situated on a quiet street in West Annapolis, the home is walkable to shops, restaurants and Navy Stadium.

Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard

10.0 out of 10, Exceptional, (16)
"Very clean, great location - easily walkable for a USNA reunion to stadium and alumni center!"
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home
2-story, riverfront home with private dock, inviting deck & dog-friendly yard

2-story, riverfront home with private dock, inviting deck & dog-friendly yard

9.6 out of 10, Exceptional, (12)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Living Area

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (32)
"We were able to walk to most places we wanted to go in town. The house was a little small but everything we needed was there and the property managers were easy to reach. We had a great time!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Charming Home in Annapolis, MD !

Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!

9.6 out of 10, Exceptional, (106)
"We were in town for a sailing event and the house was in a perfect location for us. "
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
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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Other property types in Sherwood

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home
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.