Grasonville Vacation Rentals from $150: Search Short-Term Rentals

An aerial view of a coastal residential area with houses, docks, and a clear blue sky.

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Our top choices for Grasonville vacation rentals

A kitchen with wooden cabinets, a stove, and a dining table with chairs.

1. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

$294 nightly

Nov 24 - Nov 25

Total with taxes and fees

A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

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

Stevensville

Michael V.

$285 nightly

Nov 23 - Nov 24

Total with taxes and fees

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

3. Relax on Kent Island in 4 Bedroom Home w/Waterview

Stevensville

Anthony P.

$257 nightly

Nov 15 - Nov 16

Total with taxes and fees

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

4. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

$264 nightly

Nov 21 - Nov 22

Total with taxes and fees

A house with a front porch, a pathway leading to the entrance, and a bicycle parked outside.

5. BAYSIDE BUNGALOW

Rock Hall

Diane V.

$270 nightly

Nov 15 - Nov 16

Total with taxes and fees

A beach with a wooden fence and a pier in the distance.

6. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

Sam C.

$1,122 nightly

Dec 1 - Dec 2

Total with taxes and fees

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

7. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

$136 nightly

Nov 16 - Nov 17

Total with taxes and fees

8. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

David R.

$1,141 nightly

Dec 1 - Dec 2

Total with taxes and fees

A beach with a wooden pier extending into calm waters, surrounded by greenery and a clear sky.

9. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

$405 nightly

Nov 15 - Nov 16

Total with taxes and fees

A sandy beach with lounge chairs and a small pond.

10. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Ryan C.

$414 nightly

Nov 16 - Nov 17

Total with taxes and fees

An outdoor patio with a brick wall, a grill, and metal chairs.

11. Family Retreat at Lansdowne Manor

Centreville

Emily C.

$264 nightly

Nov 15 - Nov 16

Total with taxes and fees

A two-story house with a red roof, a brick chimney, and a small porch.

12. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

Anonymous traveler

$927 nightly

Nov 16 - Nov 17

Total with taxes and fees

A calm waterfront with boats docked, a bridge in the background, and autumn foliage along the riverbank.

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

West Annapolis

Jill R.

$319 nightly

Nov 22 - Nov 23

Total with taxes and fees

A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

14. Large 2 bedroom house with private parking in a nice neighborhood

Arnold

Linda B.

$275 nightly

Nov 15 - Nov 16

Total with taxes and fees

15. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

Easton

Lynn G.

$389 nightly

Nov 30 - Dec 1

Total with taxes and fees

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

16. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

William

$462 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden cabin with a glass door, a deck, and a dock extending into calm water.

17. Houseboat Suite for Two near Annapolis

Arnold

Anonymous traveler

$321 nightly

Nov 15 - Nov 16

Total with taxes and fees

A sandy beach with a boat docked on the left and calm water.

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

Herald Harbor

Guillaume P.

$174 nightly

Nov 15 - Nov 16

Total with taxes and fees

A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

19. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Cape Saint Claire

Jennifer H.

$483 nightly

Nov 15 - Nov 16

Total with taxes and fees

A house with a stone facade, a white door with a glass panel, and a porch with two potted plants.

20. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

$466 nightly

Nov 30 - Dec 1

Total with taxes and fees

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Find vacation rentals that suit your style

Top Grasonville Hotel Reviews

A boat deck with a white bench and a view of a calm lake and distant trees.

Inn at Huntingfield Creek

Rock Hall

10/10 Excellent

George

Two Adirondack chairs facing a calm body of water with a clear sky above.

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

A two-story house with a front porch, white siding, and a black front door.

The Oaks Waterfront

Easton

10/10 Excellent

William

A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

A group of people toasting at a round table in a room with large windows and artwork on the walls.

Hummingbird Inn

Easton

10/10 Excellent

My wife and I were celebrating our 15th anniversary and the Hummingbird Inn was the perfect relaxing and romantic getaway. Eric and Michael are gracious and accommodating hosts. The Inn is gorgeous. Our room was elegant yet comfortable. There are plenty of restaurants within walking distance and lots of cool shops to check out. I also want to throw a shout out to Storm and Daughters Ice Cream which we walked to after dinner because it’s maybe the best ice cream we’ve ever had. Then back to the...

Robert

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Excellent

The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...

Richard

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

A two-story white building with a central entrance, steps, and a pink door.

134 Prince - Luxury Boutique Hotel

Annapolis

10/10 Excellent

Reyna

A church with a spire, surrounded by trees and illuminated by warm lights.

86 State Circle - Luxury Boutique Hotel

Historic District

10/10 Excellent

MARA

A large, two-story barn-style building with a covered front porch and a garage.

Kent Island Resort

Stevensville

10/10 Excellent

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

A covered outdoor area with white wicker furniture and a view of boats in the background.

Hilton Garden Inn Kent Island Marina

Grasonville

10/10 Excellent

Kathie

A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

A beach with clear water, sandy shore, and some vegetation.

Sandaway Suites & Beach

Oxford

10/10 Excellent

joseph

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

Historic Inns of Annapolis

Historic District

10/10 Excellent

Robert

Laurel Grove Inn on the South

Annapolis

10/10 Excellent

Marti

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

Parsonage Inn

Downtown St. Michaels

10/10 Excellent

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

Best Western Plus Easton Inn & Suites

Easton

10/10 Excellent

Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...

Nancy

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 $150 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.

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.

Grasonville Vacation Rentals

Check prices for these dates

Our top choices for Grasonville vacation rentals

1. Family Friendly Cozy 3 Bedroom Duplex

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

3. Relax on Kent Island in 4 Bedroom Home w/Waterview

4. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

5. BAYSIDE BUNGALOW

6. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

7. First Floor Studio Apartment in Historic Chestertown

8. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

9. Pool Loft Suite | Bay Access & Beach Passes

10. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

11. Family Retreat at Lansdowne Manor

12. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

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

14. Large 2 bedroom house with private parking in a nice neighborhood

15. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

16. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

17. Houseboat Suite for Two near Annapolis

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

19. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

20. Annapolis Retreat - 7 mins from downtown Annapolis!

Find vacation rentals that suit your style

Top Grasonville Hotel Reviews

Inn at Huntingfield Creek

10/10 Excellent

Find out more about Grasonville

Everything you need to know about Grasonville vacation rentals

Grasonville vacation rentals: An excellent choice for every season

How to find incredible deals on Grasonville rentals

Frequently Asked Questions

Can I find vacation rentals in Grasonville?

What are some of the best vacation rentals that Grasonville has to offer?

How many vacation rentals are there in Grasonville?

What can I see and do in Grasonville?

What are vacation rentals like in Grasonville?

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