Grasonville Vacation Rentals from CA $301: Short-Term Rentals for 2026

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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

Grasonville

Jamie L.

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.

Grasonville

Robin

CA $769 total

includes taxes & fees

Sep 30 - Oct 1

A modern kitchen with dark cabinets, a white countertop, and a large window.

3. Cass-N-Reel Luxury Houseboat

Grasonville

Danny B.

CA $382 total

includes taxes & fees

Oct 8 - Oct 9

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michelle P.

CA $420 total

includes taxes & fees

Oct 4 - Oct 5

Three birds perched on a wooden structure by the water.

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

Stevensville

barbara s.

CA $1,878 total

includes taxes & fees

Sep 30 - Oct 1

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!

Stevensville

David R.

CA $1,787 total

includes taxes & fees

Sep 30 - Oct 1

A building with a gabled roof and a circular vent on the roof.

7. BAYSIDE BUNGALOW

Rock Hall

Diane V.

CA $446 total

includes taxes & fees

Sep 30 - Oct 1

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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

Stevensville

Dawn G.

CA $438 total

includes taxes & fees

Oct 5 - Oct 6

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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

Rock Hall

lisa p.

CA $416 total

includes taxes & fees

Oct 4 - Oct 5

A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

10. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

CA $514 total

includes taxes & fees

Oct 1 - Oct 2

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

11. First Floor Studio Apartment in Historic Chestertown

Chestertown

"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"

Charr

CA $225 total

includes taxes & fees

Sep 30 - Oct 1

A two-story house with a red roof, a brick chimney, and a small porch.

12. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...

Suzanne R.

CA $1,494 total

includes taxes & fees

Oct 1 - Oct 2

A kitchen with wooden cabinets, a dining table, and a refrigerator.

13. Family Retreat at Lansdowne Manor

Centreville

Emily C.

CA $408 total

includes taxes & fees

Sep 30 - Oct 1

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Sharon Z.

CA $710 total

includes taxes & fees

Sep 30 - Oct 1

A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

15. Charming Annapolis WaterVIEW Home

Arundel on the Bay

Whitney M.

CA $1,005 total

includes taxes & fees

Sep 30 - Oct 1

A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

16. Secluded Cozy Cottage in Historic Downtown

Historic District

Tim G.

CA $1,228 total

includes taxes & fees

Sep 30 - Oct 1

A kitchen with a wooden countertop, a stove, and a refrigerator.

17. 18th Cent. Charm in Historic Downtown Annapolis

Historic District

Maureens B.

CA $603 total

includes taxes & fees

Sep 30 - Oct 1

A bedroom with a bed, a chair, a bedside table with a lamp, a picture on the wall, and a window with curtains.

18. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

West Annapolis

Jill R.

CA $440 total

includes taxes & fees

Oct 5 - Oct 6

A kitchen with white cabinets, a marble backsplash, and a window with a view of greenery.

19. Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Historic District

Nathan A.

CA $1,213 total

includes taxes & fees

Sep 30 - Oct 1

A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

20. Dean Street's Lower Deck House!

Historic District

Nathaniel R.

CA $705 total

includes taxes & fees

Sep 30 - Oct 1

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Top Grasonville Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"V"

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"This was a fabulous hotel. Staff was excellent very helpful. We used the shuttle to go to historic downtown. Very prompt picking us up. The drivers were so helpful and very kind. A perfect hotel to stay at especially having a shuttle not having to park in the busy historic area. The best staff we have seen at hotels."

Sonesta ES Suites Annapolis

10/10 Excellent

"We stayed in the 2 bedroom and there was plenty of room. Loved that each bedroom had a bathroom. It felt more lime staying in an apartment having your own entrance. Not having to worry about breakfast was a plus, really liked that it was included. The staff was very helpful. We did use the exercise room that was small but good enough for a quick workout to start the day. We would most definitely stay again."

Find out more about Grasonville

Everything you need to know about Grasonville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Grasonville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Grasonville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Grasonville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Grasonville. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Grasonville vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Grasonville vacation rentals we have selected for you start as low as CA $301 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Grasonville rentals

At Expedia, we put the best Grasonville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Grasonville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Grasonville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Grasonville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 10 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.

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Check prices for these dates

Our top choices for Grasonville vacation rentals

1. Cass-Away Luxury Houseboat

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

3. Cass-N-Reel Luxury Houseboat

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

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

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

7. BAYSIDE BUNGALOW

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

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

10. Bayside Cottage steps from Rock Hall Harbor

11. First Floor Studio Apartment in Historic Chestertown

12. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

13. Family Retreat at Lansdowne Manor

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

15. Charming Annapolis WaterVIEW Home

16. Secluded Cozy Cottage in Historic Downtown

17. 18th Cent. Charm in Historic Downtown Annapolis

18. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

19. Historic Downtown 3BR Crabby Patty-∙Walk to USNA

20. Dean Street's Lower Deck House!

Find vacation rentals that suit your style

Top Grasonville Hotel Reviews

Graduate by Hilton Annapolis

Hyatt Place Kent Narrows & Marina

The Inn at Chesapeake Bay Beach Club

Holiday Inn Express & Suites Annapolis by IHG

Crowne Plaza Annapolis by IHG

Annapolis Waterfront Hotel, Autograph Collection

DoubleTree by Hilton Hotel Annapolis

Courtyard by Marriott Annapolis

Sonesta ES Suites Annapolis

Find out more about Grasonville

Frequently asked questions

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