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12 Sep - 14 Sep
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19 Sep - 21 Sep
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3 Oct - 5 Oct
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31 Oct - 2 Nov

Vacation Homes in Grasonville

Our top choices for Grasonville vacation homes

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (32)
"We had 14 family members join us to celebrate my son’s graduation from the Naval Academy. The house is clean, the rooms were great, the property was beautiful, and it was close to USNA. Our family loved the open concept. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Fridge, microwave, oven, stovetop

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

10.0 out of 10, Exceptional, (40)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Marina

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (231)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Bay views with kayaks, bikes, fire pit, crabbing and more
Fridge, microwave, oven, stovetop

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (21)
"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."
Bay views with kayaks, bikes, fire pit, crabbing and more
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Property grounds

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Large 2 bedroom house with private parking in a nice neighborhood
Smart TV, books

Large 2 bedroom house with private parking in a nice neighborhood

9.4 out of 10, Exceptional, (28)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
The price is AED 624
AED 1,382 total
includes taxes & fees
1 Oct - 2 Oct
Large 2 bedroom house with private parking in a nice neighborhood
Private Cottage on gated estate
Property grounds

Private Cottage on gated estate

10.0 out of 10, Exceptional, (29)
"Convenient and great price. If you have you have younger children they will love the play area."
Private Cottage on gated estate
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA
River Front, Private Single Family Home
Property grounds

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (19)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Marina

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (29)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Entire Townhouse in Rock Hall
Exterior

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (31)
"Exactly what we expected. What wasn’t expected is how quiet and serene that entire town is. "
Entire Townhouse in Rock Hall
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Fridge, microwave, oven, stovetop

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (27)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Fridge, microwave, oven, stovetop

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10.0 out of 10, Exceptional, (12)
"The host was amazing. The property was as described and was perfect for our group. "
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Outdoor dining

Luxury Waterfront Executive Family Home Annapolis with All Amenities

10.0 out of 10, Exceptional, (2)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities
25-50% Off~Private Beach~Hot Tub~Fire Table~
Terrace/patio

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (28)
"Cute little cottage with great views and very comfortable for a small family. "
25-50% Off~Private Beach~Hot Tub~Fire Table~
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Exterior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

9.2 out of 10, Wonderful, (39)
"Great location"
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Annapolis Home Near Beach & Quiet Waters Park!
Terrace/patio

Annapolis Home Near Beach & Quiet Waters Park!

Annapolis Home Near Beach & Quiet Waters Park!
Serene Waterfront Cottage with dock and gorgeous views.
Fridge, microwave, dishwasher, coffee/tea maker

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Dining

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"The property is everything it claims to be & more. Awesome location on the bay. Great accommodations. So peaceful. We had a wonderful time. Would highly recommend! "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Historic Annapolis Home 1.5 blocks from center of town.
Terrace/patio

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (40)
"Perfect accommodations for girls weekend. Close to everything, very walkable. "
Historic Annapolis Home 1.5 blocks from center of town.
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
"Great location - easy to walk to most anywhere. Parking a bit expensive but overall experience was great "
Jason 2-night trip
Posted 21 hours ago
Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"There were two great guys at the bar; they were fun, friendly, and good company. The staff at the front desk was very knowledgeable and friendly."
Michele 3-night trip
Posted 3 days ago
Graduate by Hilton Annapolis