Search Vacation Homes in Grasonville

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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Vacation Homes in Grasonville

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, (220)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (49)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
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, (28)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Dining

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

10.0 out of 10, Exceptional, (102)
"Had a wonderful, peaceful stay."
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
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, (25)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Fridge, microwave, oven, stovetop

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

9.6 out of 10, Exceptional, (12)
"Wonderful location and just perfect for our family! "
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Fridge, microwave, oven, stovetop

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.8 out of 10, Exceptional, (20)
"Loved the stay, easy and functional for a larger group to get together in Annapolis. "
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Adorable waterside cottage with pool Beach community
Outdoor pool

Adorable waterside cottage with pool Beach community

9.4 out of 10, Exceptional, (39)
"This was a wonderful place to stay! My husband, dog, and I enjoyed our time, the pool and location near the beach were wonderful."
Adorable waterside cottage with pool Beach community
PERFECT LOCATION in the heart of history
Exterior

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (201)
"Great weekend at this property in Annapolis! Location is within walking distance to restaurants and shopping!"
PERFECT LOCATION in the heart of history
Private Cottage on gated estate
Property grounds

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Fridge, microwave, oven, stovetop

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.8 out of 10, Exceptional, (8)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is SARĀ 3,996
SARĀ 6,180 total
includes taxes & fees
23 Jun - 24 Jun
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Outdoor dining

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

10.0 out of 10, Exceptional, (44)
"Cool house within walking distance to beach, restaurant and marinas"
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Wright's Cottage- Pet's Welcome & EV Charging
TV, offices

Wright's Cottage- Pet's Welcome & EV Charging

9.8 out of 10, Exceptional, (11)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is SARĀ 525
SARĀ 1,506 total
includes taxes & fees
26 Jun - 27 Jun
Wright's Cottage- Pet's Welcome & EV Charging
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Fridge, microwave, oven, stovetop

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

10.0 out of 10, Exceptional, (4)
"Thank you for a beautiful stay! Well appointed kitchen, comfortable beds and a pristine lot. "
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (61)
"We had a wonderful stay at this property and would return in the future. Thank you!"
Recently Renovated Annapolis Home - Conveniently Located
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, (37)
"Perfect accommodations for girls weekend. Close to everything, very walkable. "
Historic Annapolis Home 1.5 blocks from center of town.
Cozy Annapolis Cottage
Terrace/patio

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (9)
"We're in the process of selling our home and used this place as our home away from home while the listing went live. It was cozy and had everything that we needed to feel like we could rest up after the difficult process of prepping our house. And a safe, fenced in yard for our dogs. It was perfect, thank you! "
Cozy Annapolis Cottage
Searenity Stays, a Cozy Home
Marina

Searenity Stays, a Cozy Home

10.0 out of 10, Exceptional, (29)
"Our stay was very comfortable here. The kitchen was well stocked for cooking, the beds were comfortable, plenty of towels, and very clean. We would definitely stay here again."
Searenity Stays, a Cozy Home
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.8 out of 10, Exceptional, (8)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!
NEW Spacious 5BDR house on serene Kent Island - close to all the hot spots!
Smart TV, fireplace

NEW Spacious 5BDR house on serene Kent Island - close to all the hot spots!

NEW Spacious 5BDR house on serene Kent Island - close to all the hot spots!
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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