Grasonville Vacation Rentals

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Our top choices for Grasonville vacation rentals

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
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 ¥38,285
¥64,444 total
includes taxes & fees
Jan 30 - Jan 31
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Turnbridge Manor

Turnbridge Manor
Denton
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 ¥54,914
¥92,973 total
includes taxes & fees
Feb 3 - Feb 4
Turnbridge Manor

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is ¥15,101
¥24,229 total
includes taxes & fees
Feb 4 - Feb 5
First Floor Studio Apartment in Historic Chestertown

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, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is ¥18,915
¥44,633 total
includes taxes & fees
Feb 13 - Feb 14
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ¥30,508
¥46,082 total
includes taxes & fees
Jan 30 - Jan 31
BAYSIDE BUNGALOW

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, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is ¥10,708
¥37,868 total
includes taxes & fees
Feb 2 - Feb 3
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is ¥31,700
¥63,023 total
includes taxes & fees
Jan 30 - Jan 31
Waterfront Oasis of Annapolis Star

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Chestertown
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."
United States
Jason
The price is ¥42,559
¥68,881 total
includes taxes & fees
Feb 21 - Feb 22
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is ¥14,058
¥42,660 total
includes taxes & fees
Feb 8 - Feb 9
Charming Coastal/Country Home w/3 Acres & Sauna!

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, (36 reviews)
"Just as advertised. Clean and quiet."
United States
Robert B.
The price is ¥19,296
¥48,708 total
includes taxes & fees
Feb 3 - Feb 4
Large 2 bedroom house with private parking in a nice neighborhood

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is ¥23,186
¥111,467 total
includes taxes & fees
Feb 9 - Feb 10
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4
Cape Saint Claire
10.0 out of 10, Exceptional, (4 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 ¥19,068
¥59,299 total
includes taxes & fees
Jan 30 - Jan 31
Luxury Pool Loft sleeps 4

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is ¥24,864
¥83,159 total
includes taxes & fees
Feb 8 - Feb 9
Cute bungalow blocks to Stadium

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
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is ¥31,700
¥76,291 total
includes taxes & fees
Feb 3 - Feb 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Historic District
9.6 out of 10, Exceptional, (27 reviews)
"Very nice place, just two of us stayed but would fit 4 comfortably. "
United States
Brad L.
The price is ¥30,508
¥54,603 total
includes taxes & fees
Feb 1 - Feb 2
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

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 ¥26,289
¥73,965 total
includes taxes & fees
Feb 1 - Feb 2
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (74 reviews)
"Great location!"
United States
Burton S.
The price is ¥26,542
¥58,429 total
includes taxes & fees
Feb 2 - Feb 3
Cozy 2br home w/ parking in downtown Annapolis

Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy
Eastport
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is ¥37,763
¥73,654 total
includes taxes & fees
Jan 30 - Jan 31
Annapolis Gem: Stylish and Cozy

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (48 reviews)
"Convenient location, very clean, beautiful yard for a pet friendly visit. We had a great time! Would go back again. "
United States
Jackie C.
The price is ¥54,228
¥70,341 total
includes taxes & fees
Jan 30 - Jan 31
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
9.8 out of 10, Exceptional, (7 reviews)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
United States
Tom D.
The price is ¥38,285
¥59,706 total
includes taxes & fees
Feb 1 - Feb 2
Walk to the stadium! - Lighthouse on Glenwood
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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Find out more about Grasonville

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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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : You might want to consider this vacation home rental near Grasonville, which is located in the city center and has a fireplace, a patio, 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Grasonville?

Choose from 13 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 Club 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.