Grasonville Holiday Rentals

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Our top choices for Grasonville holiday rentals

9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$611
includes taxes & fees
2 Feb - 3 Feb
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed the stay"
United States
Kedra B.
The price is AU$541
includes taxes & fees
26 Jan - 27 Jan
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
The price is AU$617
includes taxes & fees
28 Jan - 29 Jan
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
The price is AU$4,518
includes taxes & fees
23 Jan - 24 Jan
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is AU$239
includes taxes & fees
29 Jan - 30 Jan
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AU$386
includes taxes & fees
28 Jan - 29 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AU$396
includes taxes & fees
22 Jan - 23 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!

Holiday Home in Denton

Turnbridge Manor
9.8 out of 10, Exceptional, (12 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is AU$894
includes taxes & fees
3 Feb - 4 Feb
Turnbridge Manor
10.0 out of 10, Exceptional, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AU$426
includes taxes & fees
22 Jan - 23 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Holiday Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$412
includes taxes & fees
25 Jan - 26 Jan
BAYSIDE BUNGALOW
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is AU$977
includes taxes & fees
22 Jan - 23 Jan
Chesapeake Cottages- 2 Quaint Waterfront Retreats
10.0 out of 10, Exceptional, (8 reviews)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
HGTV quality, private guest suite, country getaway with hot tub & fire pit
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AU$717
includes taxes & fees
3 Feb - 4 Feb
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.4 out of 10, Exceptional, (36 reviews)
"Just as advertised. Clean and quiet."
United States
Robert B.
The price is AU$457
includes taxes & fees
25 Jan - 26 Jan
Large 2 bedroom house with private parking in a nice neighborhood
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is AU$802
includes taxes & fees
26 Jan - 27 Jan
Fabulous 5-bedroom house with AC in charming Annapolis

Holiday Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (14 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is AU$1,160
includes taxes & fees
2 Feb - 3 Feb
Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$596
includes taxes & fees
25 Jan - 26 Jan
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is AU$642
includes taxes & fees
25 Jan - 26 Jan
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
2.0 star property
The price is AU$340
includes taxes & fees
25 Jan - 26 Jan
Cute, Cozy 2-bedroom house in near Annapolis with water access
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful property! Water on two sides, lots of outdoor space , we had 11 people from 2-92 years staying for almost a week and had a great time. Wonderful sitting areas and screened porch. We crabbed, kayaked, had a campfire grilled. Relaxing getaway"
United States
Jody P.
The price is AU$1,081
includes taxes & fees
18 Feb - 19 Feb
Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
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$412 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?

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: This holiday home rental outside of Grasonville is located on the beach, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Grasonville?

Choose from 13 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 Club 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.