Queen Anne's County Vacation Rentals from CA $296: Short-Term Rentals for 2026

A pier extending into a body of water with a large bridge in the background.

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Top Cities in Queen Anne's County

A pier extending into a body of water with people fishing, a clear sky, and distant land with a bridge.

A white house, a horse grazing, and a field of yellow flowers.

Our top choices for Queen Anne's County vacation rentals

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

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

Stevensville

Michelle P.

CA $399 total

includes taxes & fees

Oct 18 - Oct 19

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!

Stevensville

Rebecca B.

CA $415 total

includes taxes & fees

Oct 21 - Oct 22

A deck with outdoor furniture, a potted plant, and a house in the background.

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

Chestertown

"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...

Miriam G.

CA $444 total

includes taxes & fees

Oct 28 - Oct 29

Three birds perched on a wooden structure by the water.

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

Stevensville

barbara s.

CA $1,875 total

includes taxes & fees

Oct 18 - Oct 19

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

5. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

David R.

CA $1,786 total

includes taxes & fees

Oct 21 - Oct 22

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

6. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...

Michele F.

CA $1,495 total

includes taxes & fees

Oct 21 - Oct 22

A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing a view of greenery.

7. Welcome to the secluded waterfront oasis

Millington

Destiny H.

A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

8. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena

Maria D.

CA $665 total

includes taxes & fees

Oct 18 - Oct 19

Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

9. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Arnold

Chris A.

CA $564 total

includes taxes & fees

Oct 28 - Oct 29

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

10. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

CA $225 total

includes taxes & fees

Oct 19 - Oct 20

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

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

Rock Hall

lisa p.

CA $409 total

includes taxes & fees

Oct 17 - Oct 18

A building with a gabled roof and a circular vent on the roof.

12. BAYSIDE BUNGALOW

Rock Hall

Diane V.

CA $448 total

includes taxes & fees

Oct 22 - Oct 23

A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

13. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

CA $393 total

includes taxes & fees

Oct 26 - Oct 27

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

14. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

CA $178 total

includes taxes & fees

Oct 19 - Oct 20

A spacious living area with a dining table, sofa, and a kitchen in the background.

15. Newly restored apartment in the heart of Chestertown

Chestertown

Susan A.

CA $497 total

includes taxes & fees

Oct 18 - Oct 19

Stylish kitchen with open layout and island seating

16. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

CA $693 total

includes taxes & fees

Oct 19 - Oct 20

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.

17. Turnbridge Manor

Denton

Jessica H.

CA $877 total

includes taxes & fees

Oct 28 - Oct 29

A hallway with wooden flooring, a door on the right, and a window at the end.

18. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

CA $685 total

includes taxes & fees

Oct 27 - Oct 28

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

19. Beachcomber Suite

Kent County

"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...

Lisa E.

CA $307 total

includes taxes & fees

Oct 26 - Oct 27

A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

20. Turtle Cove Room

Kent County

CA $285 total

includes taxes & fees

Oct 26 - Oct 27

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Top Queen Anne's County Hotel Reviews

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."

Historic Inns of Annapolis

10/10 Excellent

"The convenience to downtown was the biggest plus for me. The Maryland Inn is on Main street so shopping and dining are an easy walk. I was in town for the Annapolis boat show so walking to and from the show was a fairly easy commute. The hotel was very clean, my room was well maintained each day. The only issue I had was the TV was not working but upon notification, it was fixed right away. Otherwise I'd say the only other thing that visitors will be surprised with is Check in is located at another hotel (all tied to same company), so there is a short walk to this property if you are getting dropped off. Overall impression - This is an OLD historic building and hotel - actually a meeting spot for the Annapolis Ghost Tours :-). So set your expectations for that, it is not an upscale, modern resort hotel experience. For me, it was perfect, and much better than some of the rental houses I've stayed in over the years. If you're excited about historic places and buildings, this will be a great experience for you."

St Michaels Inn

10/10 Excellent

"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."

Find out more about Queen Anne's County

Everything you need to know about Queen Anne's County 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 Queen Anne's County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Queen Anne's County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Queen Anne's County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Queen Anne's County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Queen Anne's County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Queen Anne's County vacation rentals we have selected for you start as low as CA $296 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Queen Anne's County rentals

At Expedia, we put the best Queen Anne's County 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 Queen Anne's County 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 Queen Anne's County 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 Queen Anne's County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Room 1

Change your mind

Treat yourself

Be picky

Top Cities in Queen Anne's County

Stevensville

Centreville

Our top choices for Queen Anne's County vacation rentals

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

2. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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

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

5. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

6. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

7. Welcome to the secluded waterfront oasis

8. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

9. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

10. First Floor Studio Apartment in Historic Chestertown

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

12. BAYSIDE BUNGALOW

13. Secluded Cottage in Middle of Chestertown

14. Guest Suite for up to 2 in a Victorian on the Chester River

15. Newly restored apartment in the heart of Chestertown

16. Pool Loft Suite | Bay Access & Beach Passes

17. Turnbridge Manor

18. Wren Retweet- Country Estate in Center of C’Town

19. Beachcomber Suite

20. Turtle Cove Room

Find vacation rentals that suit your style

Top Queen Anne's County Hotel Reviews

The Inn at Chesapeake Bay Beach Club

Rod 'N' Reel Resort

Historic Inns of Annapolis

Microtel Inn & Suites by Wyndham Dover

Holiday Inn Express Annapolis East-Kent Island by IHG

Hilton Garden Inn Annapolis Downtown

Hyatt Place Kent Narrows & Marina

St Michaels Inn

Sonesta ES Suites Annapolis

Find out more about Queen Anne's County