The Chesapeake Bay Bridge under a brilliant blue sky on a crisp autumn day.

Grasonville Holiday Rentals

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Our top choices for Grasonville holiday rentals

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, (15 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 AU$586
includes taxes & fees
6 Aug - 7 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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$466
includes taxes & fees
4 Aug - 5 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!

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$426
includes taxes & fees
26 July - 27 July
BAYSIDE BUNGALOW

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is AU$230
includes taxes & fees
4 Aug - 5 Aug
First Floor Studio Apartment in Historic Chestertown

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, (48 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$395
includes taxes & fees
26 July - 27 July
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (15 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is AU$886
includes taxes & fees
27 July - 28 July
Turnbridge Manor

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, (26 reviews)
"Kitchen was fully stocked, apartment very clean, very nice host and parking was great"
United States
Tara K.
The price is AU$418
includes taxes & fees
26 July - 27 July
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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$521
includes taxes & fees
27 July - 28 July
Bayside Cottage steps from Rock Hall Harbor

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
25 July - 26 July
Secluded Cottage in Middle of Chestertown

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (85 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$687
includes taxes & fees
26 July - 27 July
Waterfront Oasis of Annapolis Star

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
30 July - 31 July
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is AU$845
includes taxes & fees
17 Aug - 18 Aug
Wren Retweet- Country Estate in Center of C’Town

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.
Charming Annapolis WaterVIEW Home

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$983
includes taxes & fees
4 Aug - 5 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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)
"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 AU$537
includes taxes & fees
27 July - 28 July
Large 2 bedroom house with private parking in a nice neighborhood

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, (14 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is AU$1,003
includes taxes & fees
26 July - 27 July
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is AU$1,071
includes taxes & fees
26 July - 27 July
Secluded Cozy Cottage in Historic Downtown

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, (52 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 AU$691
includes taxes & fees
26 July - 27 July
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AU$704
includes taxes & fees
10 Aug - 11 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (5 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 AU$701
includes taxes & fees
1 Aug - 2 Aug
Pool Loft Suite | Bay Access & Beach Passes
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

Find out more about Grasonville

Everything you need to know about Grasonville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Grasonville holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Grasonville holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Grasonville holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Grasonville holiday rentals we have selected for you start as low as AU$230 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Grasonville rentals

At Expedia, we put the best Grasonville holiday 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 holiday.

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 holiday rentals in Grasonville?

Yes, there are holiday rentals close to the most popular 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 holiday rentals that Grasonville has to offer?

Cute, Cozy 2-bedroom house near Annapolis with water access: This holiday home rental outside of Grasonville offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

How many holiday rentals are there in Grasonville?

Choose from 10 Expedia holiday rentals in Grasonville for a memorable holiday.

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 wider area.

What are holiday rentals like in Grasonville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Grasonville. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.