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$582
includes taxes & fees
23 Mar - 24 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
The price is AU$599
includes taxes & fees
20 Mar - 21 Mar
40' Bristol sailboat with spectacular views

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$861
includes taxes & fees
11 Mar - 12 Mar
Turnbridge Manor
9.6 out of 10, Exceptional, (108 reviews)
"Every thing was great"
United States
lesia k.
The price is AU$227
includes taxes & fees
11 Mar - 12 Mar
First Floor Studio Apartment in Historic Chestertown
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$578
includes taxes & fees
23 Mar - 24 Mar
Waterfront Oasis of Annapolis Star
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is AU$454
includes taxes & fees
11 Mar - 12 Mar
Large 2 bedroom house with private parking in a nice neighborhood
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is AU$622
includes taxes & fees
11 Mar - 12 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AU$359
includes taxes & fees
11 Mar - 12 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!

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$1,094
includes taxes & fees
31 Mar - 1 Apr
Fisher House: Steps From USNA + Covered Parking!
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$677
includes taxes & fees
23 Mar - 24 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
10.0 out of 10, Exceptional, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AU$405
includes taxes & fees
11 Mar - 12 Mar
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is AU$915
includes taxes & fees
23 Mar - 24 Mar
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is AU$695
includes taxes & fees
23 Mar - 24 Mar
Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (4 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is AU$501
includes taxes & fees
23 Mar - 24 Mar
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
10.0 out of 10, Exceptional, (2 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is AU$939
includes taxes & fees
11 Mar - 12 Mar
Golden Anchor Retreat; Lux Living! - Sleeps 7
8.0 out of 10, Very good, (3 reviews)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is AU$616
includes taxes & fees
11 Mar - 12 Mar
Fabulous 5-bedroom house with AC in charming Annapolis
9.2 out of 10, Wonderful, (5 reviews)
The price is AU$816
includes taxes & fees
11 Mar - 12 Mar
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is AU$500
includes taxes & fees
1 Apr - 2 Apr
Bayside Cottage steps from Rock Hall Harbor
9.4 out of 10, Exceptional, (20 reviews)
"Great place, excellent location!"
United States
Joseph C.
The price is AU$2,006
includes taxes & fees
11 Mar - 12 Mar
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is AU$813
includes taxes & fees
11 Mar - 12 Mar
Secluded Cozy Cottage in Historic Downtown
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$359 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?

Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit: This highly rated holiday home rental in Grasonville offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Grasonville?

Choose from 12 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.