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

Grasonville Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Grasonville vacation rentals

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

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
The price is AED 292
AED 1,018 total
includes taxes & fees
14 Oct - 15 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is AED 432
AED 1,145 total
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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)
The price is AED 455
AED 1,079 total
includes taxes & fees
13 Oct - 14 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A building with a gabled roof and a circular vent on the roof.

4. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AED 735
AED 1,159 total
includes taxes & fees
12 Oct - 13 Oct
BAYSIDE BUNGALOW
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
The price is AED 364
AED 583 total
includes taxes & fees
12 Oct - 13 Oct
First Floor Studio Apartment in Historic Chestertown
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)
The price is AED 2,935
AED 5,092 total
includes taxes & fees
11 Oct - 12 Oct
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, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is AED 2,571
AED 4,630 total
includes taxes & fees
11 Oct - 12 Oct
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A kitchen with wooden cabinets, a dining table, and a refrigerator.

8. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is AED 844
AED 1,054 total
includes taxes & fees
12 Oct - 13 Oct
Family Retreat at Lansdowne Manor
A beach with chairs and a pier 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.
The price is AED 845
AED 1,851 total
includes taxes & fees
9 Nov - 10 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

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

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A wooden dock extending into a calm body of water with boats docked at the end.

11. 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.
The price is AED 918
AED 1,746 total
includes taxes & fees
20 Oct - 21 Oct
Cozy 2br home w/ parking in downtown Annapolis
A spacious living area with a dining table, sofa, and a kitchen in the background.

12. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
The price is AED 826
AED 1,297 total
includes taxes & fees
12 Oct - 13 Oct
Newly restored apartment in the heart of Chestertown
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
8.0 out of 10, Very good, (5 reviews)
The price is AED 2,645
AED 3,870 total
includes taxes & fees
11 Oct - 12 Oct
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

14. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
The price is AED 1,322
AED 2,239 total
includes taxes & fees
13 Oct - 14 Oct
Turnbridge Manor
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

15. 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, (18 reviews)
The price is AED 1,372
AED 2,531 total
includes taxes & fees
12 Oct - 13 Oct
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

16. 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, (42 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 AED 529
AED 1,256 total
includes taxes & fees
12 Oct - 13 Oct
Large 2 bedroom house with private parking in a nice neighborhood
Stylish kitchen with open layout and island seating

17. 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.
The price is AED 834
AED 1,943 total
includes taxes & fees
9 Nov - 10 Nov
Pool Loft Suite | Bay Access & Beach Passes
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

18. 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 AED 674
AED 1,006 total
includes taxes & fees
9 Nov - 10 Nov
Secluded Cottage in Middle of Chestertown
A deck with outdoor furniture, a potted plant, and a house in the background.

19. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is AED 808
AED 1,133 total
includes taxes & fees
19 Oct - 20 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

20. 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 AED 703
AED 1,874 total
includes taxes & fees
22 Oct - 23 Oct
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Nice"
James 1-night trip
Posted 18 hours ago
Historic Inns of Annapolis

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.