A large suspension bridge spanning a wide river with a clear sky above.

Grasonville Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Grasonville vacation rentals

A modern exterior with a black door, a metal staircase, and a lantern.

1. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
The price is ￥15,439
￥48,080 total
includes taxes & fees
Sep 28 - Sep 29
Cass-Away Luxury Houseboat
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

2. 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, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is ￥38,598
￥64,644 total
includes taxes & fees
Sep 14 - Sep 15
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A modern kitchen with dark cabinets, a white countertop, and a large window.

3. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (49 reviews)
"Had a great time, great property and great location."
United States
Danny B.
The price is ￥15,439
￥43,632 total
includes taxes & fees
Oct 8 - Oct 9
Cass-N-Reel Luxury Houseboat
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is ￥18,065
￥50,013 total
includes taxes & fees
Sep 17 - Sep 18
Charming Coastal/Country Home w/3 Acres & Sauna!
A bedroom with a sloped ceiling, a bed with a striped bedspread, two red chairs, a television mounted on the wall, and a window with blinds.

5. Annapolis Charmer - Perfect Location

Annapolis Charmer - Perfect Location
Historic District
The price is ￥28,111
￥102,004 total
includes taxes & fees
Sep 15 - Sep 16
Annapolis Charmer - Perfect Location
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

6. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is ￥16,427
￥46,873 total
includes taxes & fees
Sep 16 - Sep 17
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

7. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is ￥15,207
￥24,399 total
includes taxes & fees
Sep 15 - Sep 16
First Floor Studio Apartment in Historic Chestertown
A building with a gabled roof and a circular vent on the roof.

8. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (64 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥30,722
￥48,489 total
includes taxes & fees
Sep 14 - Sep 15
BAYSIDE BUNGALOW
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

9. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is ￥130,569
￥222,787 total
includes taxes & fees
Sep 21 - Sep 22
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A spacious living area with a dining table, sofa, and a kitchen in the background.

10. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥34,562
￥54,255 total
includes taxes & fees
Sep 17 - Sep 18
Newly restored apartment in the heart of Chestertown
Three birds perched on a wooden structure by the water.

11. 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, (74 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is ￥115,793
￥204,326 total
includes taxes & fees
Sep 14 - Sep 15
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

12. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥18,095
￥44,052 total
includes taxes & fees
Sep 13 - Sep 14
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A two-story house with a red roof, a brick chimney, and a small porch.

13. 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
7.6 out of 10, Good, (4 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 traveler
The price is ￥110,599
￥161,849 total
includes taxes & fees
Sep 16 - Sep 17
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A beach with chairs and a pier in the background.

14. 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)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
The price is ￥27,095
￥69,785 total
includes taxes & fees
Sep 14 - Sep 15
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

15. 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
9.0 out of 10, Wonderful, (16 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is ￥48,387
￥92,986 total
includes taxes & fees
Sep 15 - Sep 16
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

16. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is ￥38,042
￥98,632 total
includes taxes & fees
Sep 13 - Sep 14
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
A wooden dock extending into a calm body of water with boats docked at the end.

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is ￥34,562
￥68,120 total
includes taxes & fees
Sep 13 - Sep 14
Cozy 2br home w/ parking in downtown Annapolis
A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

18. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥34,869
￥65,456 total
includes taxes & fees
Sep 28 - Sep 29
Bayside Cottage steps from Rock Hall Harbor

19. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is ￥29,585
￥74,004 total
includes taxes & fees
Sep 13 - Sep 14
Pool Loft Suite | Bay Access & Beach Passes
A two-story house with a covered patio, a garage, and a well-maintained lawn.

20. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (54 reviews)
"Great stay in Annapolis. The property is gorgeous. Everything you need for a great weekend in Annapolis. "
United States
Jennifer G.
The price is ￥58,756
￥75,738 total
includes taxes & fees
Sep 16 - Sep 17
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

8/10 Good
"Not able to stream TV. Uncomfortable bed and bedding was noticeably worn"
Margretann 1-night trip
Posted 5 hours ago
Hilton Garden Inn Annapolis Downtown

Find out more about Grasonville

Search for holiday rentals in Grasonville on Expedia! You can easily find your home rentals, villas, holiday apartments in Grasonville using one of the methods below:

  • View our selection of featured holiday rentals in Grasonville
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  • Enter your travel dates to view the best deals on holiday rentals in Grasonville while they last

Look no further and take a look at our great range of rental properties in Grasonville!

Frequently asked questions

Can I find vacation rentals in Grasonville?

Yes, there are vacation rentals close to top sights in Grasonville, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and marina in Grasonville. Leave plenty of time to check out the shops and beaches during your trip.

What are some of the best vacation rentals that Grasonville has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Grasonville vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Grasonville?

Choose from 9 Expedia vacation rentals in Grasonville for a memorable vacation.

What can I see and do in Grasonville?

While exploring the area, visit family-friendly sights like Chesapeake Bay Maritime Museum, or get outside and enjoy nature at Chesapeake Bay Environmental Center. Queenstown Harbor Golf and Queenstown Premium Outlets are a couple of places you'll find in the larger area.

What are vacation rentals like in Grasonville?

Vacation rentals are private accommodations you can reserve for a short or long stay in Grasonville. Vacation rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.