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Compare 546 Vacation Homes in Grasonville with updated reviews, rates, and availability.

Pet-Friendly Home on Chester River w/ Dock!
Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.0 out of 10, Wonderful, (2)
"no kettle no cutting board"
Pet-Friendly Home on Chester River w/ Dock!
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, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Calloway Drive Retreat | House in Shady Side

Calloway Drive Retreat | House in Shady Side

9.2 out of 10, Wonderful, (5)
"We had lots of room to relax and hang out. The kitchen is very well appointed and we definitely could have cooked if we chose to. We enjoyed walking with nice views of the ocean. We especially enjoyed the osprey hanging out near their nest right off the pier."
Calloway Drive Retreat | House in Shady Side
Dollhouse in Central Historic St Michaels
Front of House

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (46)
"This was a comfortable home, and a nice location. We were staying mostly for business, so didn’t do much in town, but the main restaurant and shopping areas are two short blocks away. We did use the nearby nature trail to walk our dogs. The only concerns others might have with the house, and the reason for four stars instead of five, were: minimal kitchen equipment (few pots/pans etc.), steep narrow stairs to the second floor, and low water pressure in the shower. That said, none of these things...
Dollhouse in Central Historic St Michaels
Private Waterfront Woods | Dock, Kayaks, Views

Private Waterfront Woods | Dock, Kayaks, Views

9.6 out of 10, Exceptional, (16)
"Enjoyed the location and proximity to the city. Water view and firepit enjoyable. Disappointed that the dock and kayaks not easily accessible. House needs some tlc (we provided a list of easy repairs/maintenance needed.) Love to know why the ceiling fans and lights go on and off randomly."
Private Waterfront Woods | Dock, Kayaks, Views
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, (73)
"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
Waterfront family resort Lodge with private pier, game room and bar
The Twin Ponds Lodge sits on over 7 acres of private waterfront property.

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (23)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Living/Kitchen

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (13)
"We very much enjoyed our stay. The house is exactly as described and we would stay here again if we are in Annapolis again. The house has everything you need with a fully equipped kitchen, smart tvs in every room, and the beds are very comfortable. There is so much parking and the house is walking distance to everything in downtown Annapolis and the Naval Academy. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Brand New Spacious Luxury Home
Welcome to Bay Ridge - a 4-bedroom and 4.5-bath luxury home in Eastport - 1-mile to downtown

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (3)
"From communication to check-in and cleanliness, this VRBO has plenty of room and modern amenities. What put this over the top was that a party member left the wallet at the VRBO, and the renters went and retrieved the wallet and met us to return it. They went above and beyond to help us. It has a good backyard and can park 3-4 cars in the driveway; this VRBO has everything. Easily five stars"
Brand New Spacious Luxury Home
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront with private pier and great views

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Relax on Kent Island in 3 Bedroom Home w/Waterview
Room

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (32)
"Perfect for our weekend stay. Checkin was easy and communication with the owner was great! Definitely would stay again. Kentmoor restaurant was awesome. Filled with locals who were friendly and welcoming! Food was great!"
The price is SAR 296
SAR 958 total
includes taxes & fees
5 Jan - 6 January 2025
Relax on Kent Island in 3 Bedroom Home w/Waterview
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Exterior

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (102)
"Awesome House Awesome neighborhood Awesome Host(ess). 10 out of 10"
The price is SAR 1,502
SAR 1,948 total
includes taxes & fees
12 Jan - 13 January 2025
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Walk to Everything House
Front of House

Walk to Everything House

10.0 out of 10, Exceptional, (74)
"House was centrally located in town. We parked the car and walked! Beds were very comfortable it was wonderful to have seperate beds for everyone. Well stocked kitchen. Washer & dryer a plus. We will be back. "
Walk to Everything House
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
FAMILY ROOM W/FIREPLACE & FLAT SCREEN TV

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

9.8 out of 10, Exceptional, (27)
"Felt like home as soon as we walked in...except it was CLEANER than home :-) Comfortable, spacious, well-stocked. Hosts were attentive & quick to answer messages. Great experience!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
5/17/2022- Just updated!!

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (24)
"The Ranch at Royal Oak was a fantastic property. The property was exactly as advertised - gorgeous waterfront estate with a large lawn. Incredibly peaceful. We were looking for a getaway to hit pause and just relax and the ranch Royal Oak was exactly what we needed. Marissa was a great host - incredibly responsive, check in instructions are very clear.and easy to follow. I highly recommend this property for your next getaway."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Bennett House (entire):Haven in Historic Annapolis
First floor kitchen

Bennett House (entire):Haven in Historic Annapolis

10.0 out of 10, Exceptional, (12)
"Great place, wonderful location "
Bennett House (entire):Haven in Historic Annapolis
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Beach

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (62)
"Bigger, nicer and newer than it looks in the pics; a pleasant surprise. Great location, we’d go again. "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Historic Annapolis Home 1.5 blocks from center of town.
Exterior

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (29)
"We loved our weekend here! The house was just as described. Location was perfect to be able to walk to everything downtown, yet far enough away that it was quiet. Loved the charm of the house, bed was very comfortable, and it had everything we needed. We would definitely return! "
Historic Annapolis Home 1.5 blocks from center of town.
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 Grasonville

Cass-Away Luxury Houseboat
Miscellaneous

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (89)
"This is a great getaway place!! Very nice on the water. Lots to do in the area! Tiki Bars restaurants must stop while traveling or vacationing!"
Cass-Away Luxury Houseboat
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, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.