Search Vacation Homes in Grasonville

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Grasonville vacation homes

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

Vacation Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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
22 Dec - 23 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Property grounds
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Vacation Home in Queen Anne

Adorable two-bedroom retreat close to Easton, Denton, Centreville
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
The price is AED 694
AED 1,316 total
includes taxes & fees
22 Dec - 23 Dec
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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 194
AED 825 total
includes taxes & fees
14 Dec - 15 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Vacation Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
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 377
AED 1,061 total
includes taxes & fees
21 Dec - 22 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!
Property grounds
Turnbridge Manor

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 2,414 total
includes taxes & fees
29 Dec - 30 Dec
Turnbridge Manor
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Vacation Home in Centreville

HGTV quality, private guest suite, country getaway with hot tub & fire pit
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 1,628 total
includes taxes & fees
17 Dec - 18 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Vacation Home in Rock Hall

Chesapeake Bay Harbor View in a central location to events/restaurants
2.5 star property
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
23 Dec - 24 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Vacation Home in Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is AED 529
AED 1,566 total
includes taxes & fees
12 Dec - 13 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

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 657
AED 1,975 total
includes taxes & fees
16 Dec - 17 Dec
Neptune by the Water - Pet Friendly Fenced Yard
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Vacation Home in Arnold

Large 2 bedroom house with private parking in a nice neighborhood
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
14 Dec - 15 Dec
Large 2 bedroom house with private parking in a nice neighborhood
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in Annapolis

Charming Pet-Friendly Stay - Near Bay & Beaches.
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.
Outdoor dining
BAYSIDE BUNGALOW

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
1 Jan - 2 January 2026
BAYSIDE BUNGALOW
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

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
14 Dec - 15 Dec
Cute bungalow blocks to Stadium
TV, offices
Wright's Cottage- Pet's Welcome & EV Charging

Vacation Home in Annapolis

Wright's Cottage- Pet's Welcome & EV Charging
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
TV, books, offices
Holly Hill Haven - Sleeps 10

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 654
AED 1,966 total
includes taxes & fees
6 Jan - 7 January 2026
Holly Hill Haven - Sleeps 10
4 bedrooms, desk, iron/ironing board, travel crib
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Vacation Home in Homewood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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 744
AED 1,798 total
includes taxes & fees
15 Dec - 16 Dec
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Property grounds
New! Stylish downtown home w/awesome outdoor area!

Vacation Home in Stevensville

New! Stylish downtown home w/awesome outdoor area!
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 810
AED 1,847 total
includes taxes & fees
25 Dec - 26 Dec
New! Stylish downtown home w/awesome outdoor area!
Interior
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!

Vacation Home in Historic District

Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
The price is AED 496
AED 2,583 total
includes taxes & fees
15 Dec - 16 Dec
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Vacation Home in Arundel on the Bay

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AED 926
AED 2,027 total
includes taxes & fees
19 Dec - 20 Dec
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Terrace/patio
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Vacation Home in Eastport

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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great"
stephen 3-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis