Holiday Homes in Grasonville

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Find holiday rentals that suit your style

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Apartments
Apartments
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Cottages
Cottages

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Grasonville holiday homes

A kitchen with wooden cabinets, a stove, and a dining table with chairs.

1. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is €279
includes taxes & fees
11 Dec - 12 Dec
Family Friendly Cozy 3 Bedroom Duplex
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is €293
includes taxes & fees
23 Nov - 24 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

3. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is €252
includes taxes & fees
15 Nov - 16 Nov
Relax on Kent Island in 4 Bedroom Home w/Waterview
An outdoor seating area with tables and chairs, umbrellas, and a view of the water.

4. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Great stay, exactly as advertised, Donna was great!"
United States
Sam C.
The price is €1,148
includes taxes & fees
6 Dec - 7 Dec
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A building with a gabled roof and a circular vent on the roof.

5. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is €273
includes taxes & fees
14 Nov - 15 Nov
BAYSIDE BUNGALOW
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

6. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is €1,138
includes taxes & fees
1 Dec - 2 Dec
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A beach with chairs and a pier in the background.

7. 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, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is €430
includes taxes & fees
16 Nov - 17 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A two-story house with a red roof, a brick chimney, and a small porch.

8. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.6 out of 10, Excellent, (7 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is €887
includes taxes & fees
23 Nov - 24 Nov
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

9. 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, (44 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is €288
includes taxes & fees
15 Nov - 16 Nov
Large 2 bedroom house with private parking in a nice neighborhood
A kitchen with wooden cabinets, a dining table, and a refrigerator.

10. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is €261
includes taxes & fees
15 Nov - 16 Nov
Family Retreat at Lansdowne Manor
A sandy beach with a boat docked on the left and calm water.

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (31 reviews)
"Great stay"
United States
Guillaume P.
The price is €183
includes taxes & fees
15 Nov - 16 Nov
Cute, Cozy 2-bedroom house near Annapolis with water access
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

12. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is €523
includes taxes & fees
17 Nov - 18 Nov
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

13. 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 €484
includes taxes & fees
30 Nov - 1 Dec
Annapolis Retreat - 7 mins from downtown Annapolis!
A wooden dock extending into a calm body of water with boats docked at the end.

14. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (87 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is €375
includes taxes & fees
16 Nov - 17 Nov
Cozy 2br home w/ parking in downtown Annapolis
A backyard patio with a round table and chairs, surrounded by a gravel area.

15. 5 bedroom house with EV charger Near Downtown Annapolis

5 bedroom house with EV charger Near Downtown Annapolis
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"In town for a regatta, exactly what we required. "
United States
Jacob V.
The price is €542
includes taxes & fees
15 Nov - 16 Nov
5 bedroom house with EV charger Near Downtown Annapolis
A spacious living room with a large sofa, a coffee table, and a chandelier. There is a kitchen in the background with a dining area.

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

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (10 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is €543
includes taxes & fees
17 Nov - 18 Nov
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
A living room with a grey sofa, a painting of sailboats, a dining table with chairs, and a lamp.

17. Historic 2BR + Loft Home in Downtown Annapolis

Historic 2BR + Loft Home in Downtown Annapolis
Historic District
Historic 2BR + Loft Home in Downtown Annapolis
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

18. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 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 €474
includes taxes & fees
14 Nov - 15 Nov
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

19. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is €695
includes taxes & fees
14 Dec - 15 Dec
Family Home on Mayo Peninsula | Deck | Sleeps 10
A two-story house with a stone pathway leading to the front door, surrounded by lush greenery and other houses.

20. Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
9.8 out of 10, Exceptional, (12 reviews)
"The home was well stocked with all the items needed to cook and spotless. Very comfortable and easy walk to the Navy stadium. Enjoyed our stay and all that Annapolis has to share. "
United States
Veronica D.
The price is €792
includes taxes & fees
15 Nov - 16 Nov
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
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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Learn more about Grasonville

Fresh Chesapeake Bay seafood awaits at waterfront restaurants where you can watch boats dock with the day's catch. Explore nearby Kent Narrows' maritime heritage or rent kayaks to paddle through peaceful Eastern Shore marshlands teeming with herons and osprey.

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