An aerial view of a coastal residential area with houses, docks, and a clear blue sky.

Holiday Homes in Grasonville

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Grasonville holiday homes

Exterior

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, (47 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is AU$417
includes taxes & fees
22 July - 23 July
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (41 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is AU$495
includes taxes & fees
3 Aug - 4 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$429
includes taxes & fees
21 July - 22 July
BAYSIDE BUNGALOW
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is AU$542
includes taxes & fees
27 July - 28 July
Bayside Cottage steps from Rock Hall Harbor
Interior

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, (40 reviews)
"Just was very responsive to all requests and inquiries."
United States
Vesta M.
The price is AU$530
includes taxes & fees
27 July - 28 July
Large 2 bedroom house with private parking in a nice neighborhood
Coffee/tea maker, fridge, microwave, oven

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (9 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is AU$833
includes taxes & fees
23 July - 24 July
Renovated Bungalow | Walk to Beach | Dog-Friendly
Coffee/tea maker, fridge, microwave, oven

Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (14 reviews)
"Highly recommend this property! Great location. Place is clean and host was very accommodating."
United States
Abi O.
The price is AU$337
includes taxes & fees
27 July - 28 July
Cute, Cozy 2-bedroom house near Annapolis with water access
Outdoor dining

Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (1 review)
"Great spot! Amazing amount of room. Great communication in ease of check-in"
United States
Jeffrey T.
Waterfront Escape with Pool Nature Lover Paradise
Coffee/tea maker, fridge, microwave, oven

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is AU$1,003
includes taxes & fees
21 July - 22 July
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$793
includes taxes & fees
18 Aug - 19 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
TV, fireplace

Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is AU$400
includes taxes & fees
21 July - 22 July
Secluded Cottage in Middle of Chestertown
Terrace/patio

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
The price is AU$512
includes taxes & fees
23 July - 24 July
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
TV, offices

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AU$1,003
includes taxes & fees
21 July - 22 July
Family Home on Mayo Peninsula | Deck | Sleeps 10
Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is AU$815
includes taxes & fees
21 July - 22 July
Historic Row Home in Downtown Annapolis
Exterior detail

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is AU$841
includes taxes & fees
21 July - 22 July
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Coffee/tea maker, fridge, microwave, oven

Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Very recent remodel, and all top notch. You can tell the owners put their heart and soul into this property. All the rooms have been very nicely done. Bathrooms were beautifully done. Beds were comfortable. The area is very peaceful and quiet. We really enjoyed the back yard space also. Sat at patio table and used grill. Large TV’s everywhere! We were able to sit at patio table, grill some burgers and watch Final Four games from TV in kitchen area. If you have a Midshipman, this property is...
United States
Brian S.
The price is AU$1,775
includes taxes & fees
22 July - 23 July
Luxe Row Home Steps to USNA Gate 3!
Coffee/tea maker, fridge, microwave, oven

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is AU$754
includes taxes & fees
22 July - 23 July
Cute bungalow blocks to Stadium
Beach nearby, sun-loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AU$968
includes taxes & fees
18 Aug - 19 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is AU$1,072
includes taxes & fees
3 Aug - 4 Aug
Charming Annapolis WaterVIEW Home
Coffee/tea maker, fridge, microwave, oven

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is AU$1,098
includes taxes & fees
21 July - 22 July
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Grasonville Hotel Reviews

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"I loved the hotel. The staff was fantastic. My one and only complaint if even a complaint is they could have more choices on the dinner menu."
Lena 2-night trip
Posted less than an hour ago
The Westin Annapolis

Find out more about Grasonville

Grasonville Holiday Homes information

Number of reviews
Accommodation
 Holiday Homes
Lowest Price
Highest Price