Search Vacation Homes in Grasonville

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Vacation Homes in Grasonville

Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville
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.
$395 nightly
The price is $419
Dec 9 - Dec 10
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville
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.
$240 nightly
The price is $254
Dec 11 - Dec 12
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville
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
$234 nightly
The price is $248
Dec 9 - Dec 10
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Property grounds
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Queen Anne
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
$338 nightly
The price is $358
Dec 22 - Dec 23
Total with taxes and fees
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

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.
$420 nightly
The price is $445
Dec 15 - Dec 16
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Property grounds
Turnbridge Manor

Turnbridge Manor

Denton
9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
$613 nightly
The price is $650
Dec 29 - Dec 30
Total with taxes and fees
Turnbridge Manor
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard

Cape Saint Claire
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.
$469 nightly
The price is $498
Dec 9 - Dec 10
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
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.
$257 nightly
The price is $272
Dec 9 - Dec 10
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood

Arnold
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.
$285 nightly
The price is $324
Dec 9 - Dec 10
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$376 nightly
The price is $429
Dec 9 - Dec 10
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
4 bedrooms, desk, iron/ironing board, travel crib
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Homewood
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.
$402 nightly
The price is $458
Dec 9 - Dec 10
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Marina
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Historic District
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.
$268 nightly
The price is $306
Dec 9 - Dec 10
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.

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
$494 nightly
The price is $563
Dec 15 - Dec 16
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium

Admiral Heights
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.
$460 nightly
The price is $520
Dec 15 - Dec 16
Total with taxes and fees
Cute bungalow blocks to Stadium
TV, offices
Wright's Cottage- Pet's Welcome & EV Charging

Wright's Cottage- Pet's Welcome & EV Charging

Annapolis
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.
$327 nightly
The price is $372
Dec 10 - Dec 11
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$262 nightly
The price is $278
Jan 1 - Jan 2, 2026
Total with taxes and fees
BAYSIDE BUNGALOW
Property grounds
New! Stylish downtown home w/awesome outdoor area!

New! Stylish downtown home w/awesome outdoor area!

Stevensville
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.
$502 nightly
The price is $532
Dec 25 - Dec 26
Total with taxes and fees
New! Stylish downtown home w/awesome outdoor area!
Fridge, microwave, oven, stovetop
Fisher House: Steps From USNA + Covered Parking!

Fisher House: Steps From USNA + Covered Parking!

Historic District
10.0 out of 10, Exceptional, (13)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
$532 nightly
The price is $569
Dec 9 - Dec 10
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!
TV, books, offices
Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10

Edgewater
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$502 nightly
The price is $537
Jan 5 - Jan 6, 2026
Total with taxes and fees
Holly Hill Haven - Sleeps 10
Terrace/patio
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Eastport
$277 nightly
The price is $316
Dec 9 - Dec 10
Total with taxes and fees
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."
Paul 1-night trip
Posted 8 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

Find out more about Grasonville

Grasonville Vacation Homes information

Number of reviews
370
Accommodation
646 Vacation Homes
Lowest Price
$248
Highest Price
$650

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