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

Grasonville Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Grasonville vacation rentals

A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (48 reviews)
"Great stay"
United States
Michael V.
$265 nightly
The price is $285
Oct 25 - Oct 26
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

2. 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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
$271 nightly
The price is $292
Oct 26 - Oct 27
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A house with a blue front door, two windows, and a small porch.

3. 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.
$264 nightly
The price is $292
Oct 25 - Oct 26
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Oct 26 - Oct 27
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A building with a gabled roof and a circular vent on the roof.

5. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$286 nightly
The price is $316
Oct 23 - Oct 24
Total with taxes and fees
BAYSIDE BUNGALOW
Three birds perched on a wooden structure by the water.

6. 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, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
$1,199 nightly
The price is $1,323
Oct 25 - Oct 26
Total with taxes and fees
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

7. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
$1,126 nightly
The price is $1,244
Oct 26 - Oct 27
Total with taxes and fees
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stylish kitchen with open layout and island seating

8. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (8 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$441 nightly
The price is $503
Oct 25 - Oct 26
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
A hot tub with a white deck and railing, surrounded by trees and a house in the background.

9. 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)
"The perfect off-season get-away! "
United States
Pamela B.
$447 nightly
The price is $510
Nov 3 - Nov 4
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A waterfront walkway with a brick path, a lamp post, and a bench.

10. 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.
$423 nightly
The price is $482
Nov 2 - Nov 3
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
A bedroom with a bed, a desk, a chair, a ceiling fan, a TV, and a window.

11. 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, (43 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.
$293 nightly
The price is $333
Oct 25 - Oct 26
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
A kitchen with wooden cabinets, granite countertops, and a dining table set with blue and white dishes.

12. 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
$486 nightly
The price is $554
Oct 25 - Oct 26
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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
8.4 out of 10, Very good, (6 reviews)
"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...
United States
Michele F.
$994 nightly
The price is $1,054
Oct 24 - Oct 25
Total with taxes and fees
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

14. 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
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
$505 nightly
The price is $575
Oct 25 - Oct 26
Total with taxes and fees
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

15. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."
United States
Anonymous traveler
$319 nightly
The price is $363
Oct 28 - Oct 29
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

16. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$503 nightly
The price is $573
Nov 17 - Nov 18
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

17. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (28 reviews)
"The property was very clean nice open kitchen and comfortable rooms . Very nice experience definitely recommend."
United States
Antonio
$183 nightly
The price is $208
Oct 28 - Oct 29
Total with taxes and fees
Cute, Cozy 2-bedroom house near Annapolis with water access
A modern kitchen with a central island, built-in oven, and microwave.

18. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
$458 nightly
The price is $519
Oct 26 - Oct 27
Total with taxes and fees
Cute bungalow blocks to Stadium
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

19. 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.
$264 nightly
The price is $274
Oct 25 - Oct 26
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

20. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
$505 nightly
The price is $576
Oct 25 - Oct 26
Total with taxes and fees
Renovated Bungalow | Walk to Beach | Dog-Friendly
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Very pleasant surprise! Great price for studio apartment- way better than the Marriott I just checked out of!"
Rhonda 1-night trip
Posted 6 hours ago
Sonesta ES Suites Annapolis

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Grasonville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $208 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.