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Queen Anne's County Holiday Rentals

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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.
Vacation Rentals

Stevensville

Stevensville

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Queen Anne's County holiday rentals

A deck with a view of a marina, including boats and docks.

1. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
Cass-N-Reel Luxury Houseboat
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 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is AU$447
includes taxes & fees
23 Nov - 24 Nov
Relax on Kent Island in 4 Bedroom Home w/Waterview
A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (51 reviews)
"Great stay"
United States
Michael V.
The price is AU$447
includes taxes & fees
23 Nov - 24 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"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...
United States
Miriam G.
The price is AU$404
includes taxes & fees
30 Nov - 1 Dec
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A kitchen with wooden cabinets, a stove, and a dining table with chairs.

5. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is AU$450
includes taxes & fees
24 Nov - 25 Nov
Family Friendly Cozy 3 Bedroom Duplex
An outdoor patio with a brick wall, a grill, and metal chairs.

6. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is AU$433
includes taxes & fees
16 Nov - 17 Nov
Family Retreat at Lansdowne Manor
A beach with a wooden fence and a pier in the distance.

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

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Great stay, exactly as advertised, Donna was great!"
United States
Sam C.
The price is AU$1,805
includes taxes & fees
1 Dec - 2 Dec
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A beach with a wooden fence and a pier in the distance.

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

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is AU$1,805
includes taxes & fees
1 Dec - 2 Dec
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A two-story house with a red roof, a brick chimney, and a small porch.

9. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.6 out of 10, Excellent, (7 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is AU$1,436
includes taxes & fees
16 Nov - 17 Nov
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

10. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (134 reviews)
"Easy to find and good parking. Nice quiet neighborhood. Has refrigerator and microwave. Excellent hot water. Thanks"
United States
Donna G.
The price is AU$224
includes taxes & fees
16 Nov - 17 Nov
First Floor Studio Apartment in Historic Chestertown
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!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (36 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AU$431
includes taxes & fees
21 Nov - 22 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A person sitting on a wooden deck by a calm body of water, surrounded by greenery.

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (34 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is AU$174
includes taxes & fees
18 Nov - 19 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
A house with a front porch, a pathway leading to the entrance, and a bicycle parked outside.

13. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Great hosts… come to Rock Hall every year and found this cute cottage…will def come here every year. Great place"
United States
Nanci H.
The price is AU$437
includes taxes & fees
16 Nov - 17 Nov
BAYSIDE BUNGALOW
A spacious room with a large sliding glass door leading to a deck, a sofa, a chair, and a small table.

14. Bay Sunsets for Two • Rooftop Fire Pit

Bay Sunsets for Two • Rooftop Fire Pit
Pasadena
10.0 out of 10, Exceptional, (4 reviews)
"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"
United States
Charles W.
The price is AU$636
includes taxes & fees
19 Nov - 20 Nov
Bay Sunsets for Two • Rooftop Fire Pit
A beach with a wooden pier extending into calm waters, surrounded by greenery and a clear sky.

15. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 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 AU$675
includes taxes & fees
16 Nov - 17 Nov
Pool Loft Suite | Bay Access & Beach Passes
A living room with two grey sofas, a coffee table, and a ceiling fan.

16. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is AU$477
includes taxes & fees
16 Nov - 17 Nov
Cambridge Apt in Walkable Neighborhood
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

17. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is AU$225
includes taxes & fees
29 Nov - 30 Nov
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Living area

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

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
The price is AU$611
includes taxes & fees
30 Nov - 1 Dec
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A wooden cabin with a glass door, a deck, and a dock extending into calm water.

19. Houseboat Suite for Two near Annapolis

Houseboat Suite for Two near Annapolis
Arnold
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."
United States
Anonymous traveller
The price is AU$549
includes taxes & fees
19 Nov - 20 Nov
Houseboat Suite for Two near Annapolis
A bedroom with a bunk bed, a single bed, a desk, and a chair.

20. Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
9.6 out of 10, Exceptional, (25 reviews)
"We enjoy this place!!!"
United States
nahum f.
The price is AU$357
includes taxes & fees
23 Nov - 24 Nov
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
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 holiday rentals that suit your style

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Condos
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Top Queen Anne's County Hotel Reviews

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

Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels

10/10 Excellent

The Inn at Perry Cabin is a beautiful, luxurious hotel in a lovely setting. Our room was elegant and comfortable we had turn down service each night with cookies and slippers left for us. The staff is helpful and friendly. There are fresh flowers and plants throughout the hotel and the grounds are beautifully landscaped. The only negative is that they charge $50 a day to use the fitness facilities! Surprising at a very expensive hotel.
Australia
2revs
Reviewed April 17, 2015
Inn at Perry Cabin

Find out more about Queen Anne's County

Everything you need to know about Queen Anne's County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Queen Anne's County holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Queen Anne's County holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Queen Anne's County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Queen Anne's County holiday rentals we have chosen for you start as low as AU$173 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 holiday 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 holiday.

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.