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Our top choices for Grasonville vacation homes

9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AED 918
AED 1,538 total
includes taxes & fees
11 Dec - 12 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AED 234
AED 890 total
includes taxes & fees
11 Dec - 12 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is AED 278
AED 944 total
includes taxes & fees
14 Dec - 15 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
The price is AED 676
AED 1,293 total
includes taxes & fees
22 Dec - 23 Dec
Adorable two-bedroom retreat close to Easton, Denton, Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is AED 724
AED 1,635 total
includes taxes & fees
15 Dec - 16 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Vacation Home in Denton

Turnbridge Manor
9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is AED 1,469
AED 2,386 total
includes taxes & fees
29 Dec - 30 Dec
Turnbridge Manor

Vacation Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is AED 672
AED 1,992 total
includes taxes & fees
16 Dec - 17 Dec
Neptune by the Water - Pet Friendly Fenced Yard
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is AED 826
AED 1,001 total
includes taxes & fees
11 Dec - 12 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants
9.4 out of 10, Exceptional, (36)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
The price is AED 479
AED 1,191 total
includes taxes & fees
11 Dec - 12 Dec
Large 2 bedroom house with private parking in a nice neighborhood
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is AED 529
AED 1,574 total
includes taxes & fees
11 Dec - 12 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
The price is AED 694
AED 1,729 total
includes taxes & fees
16 Dec - 17 Dec
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Vacation Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
The price is AED 701
AED 1,478 total
includes taxes & fees
5 Jan - 6 January 2026
Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
The price is AED 862
AED 2,067 total
includes taxes & fees
15 Dec - 16 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (7)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is AED 536
AED 1,910 total
includes taxes & fees
15 Dec - 16 Dec
Cute bungalow blocks to Stadium
9.2 out of 10, Wonderful, (16)
"Great location, cozy cottage, good for dogs, lots to do in and around Annapolis. "
United States
Mike F.
The price is AED 680
AED 1,407 total
includes taxes & fees
15 Dec - 16 Dec
Wright's Cottage- Pet's Welcome & EV Charging

Vacation Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AED 735
AED 1,110 total
includes taxes & fees
6 Jan - 7 January 2026
BAYSIDE BUNGALOW
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
The price is AED 900
AED 1,954 total
includes taxes & fees
25 Dec - 26 Dec
New! Stylish downtown home w/awesome outdoor area!

Vacation Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (13)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is AED 1,139
AED 2,637 total
includes taxes & fees
11 Dec - 12 Dec
Fisher House: Steps From USNA + Covered Parking!

Vacation Home in Edgewater

Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AED 639
AED 1,936 total
includes taxes & fees
5 Jan - 6 January 2026
Holly Hill Haven - Sleeps 10
The price is AED 569
AED 1,168 total
includes taxes & fees
15 Dec - 16 Dec
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
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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Top Grasonville Hotel Reviews