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Queen Anne's County Vacation 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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Queen Anne's County vacation 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
The price is CA $127
CA $366 total
includes taxes & fees
Nov 12 - Nov 13
Cass-N-Reel Luxury Houseboat
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is CA $135
CA $409 total
includes taxes & fees
Nov 10 - Nov 11
Charming Coastal/Country Home w/3 Acres & Sauna!
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

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 CA $195
CA $481 total
includes taxes & fees
Nov 23 - Nov 24
Relax on Kent Island in 4 Bedroom Home w/Waterview
An outdoor seating area with tables and chairs, umbrellas, and a view of the water.

4. 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 CA $980
CA $1,765 total
includes taxes & fees
Dec 1 - Dec 2
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

5. 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 CA $278
CA $389 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A kitchen with wooden cabinets, a dining table, and a refrigerator.

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 CA $322
CA $371 total
includes taxes & fees
Nov 8 - Nov 9
Family Retreat at Lansdowne Manor
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

7. 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 CA $980
CA $1,765 total
includes taxes & fees
Dec 1 - Dec 2
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A kitchen with wooden cabinets, a stove, and a dining table with chairs.

8. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is CA $378
CA $437 total
includes taxes & fees
Nov 10 - Nov 11
Family Friendly Cozy 3 Bedroom Duplex
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
8.4 out of 10, Very good, (6 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 CA $1,009
CA $1,404 total
includes taxes & fees
Nov 9 - Nov 10
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, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $139
CA $211 total
includes taxes & fees
Nov 9 - Nov 10
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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $182
CA $404 total
includes taxes & fees
Nov 17 - Nov 18
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A garden with a wooden bridge, lush greenery, and a variety of plants.

12. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is CA $257
CA $368 total
includes taxes & fees
Nov 8 - Nov 9
Secluded Cottage in Middle of Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

13. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is CA $315
CA $451 total
includes taxes & fees
Nov 8 - Nov 9
Newly restored apartment in the heart of Chestertown
A building with a gabled roof and a circular vent on the roof.

14. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $280
CA $402 total
includes taxes & fees
Nov 8 - Nov 9
BAYSIDE BUNGALOW
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

15. 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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is CA $95
CA $163 total
includes taxes & fees
Nov 9 - Nov 10
Guest Suite for up to 2 in a Victorian on the Chester River
A calm waterfront with boats docked, a bridge in the background, and autumn foliage along the riverbank.

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

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A covered porch with a wooden bench, potted plants, and a decorative railing.

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

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is CA $427
CA $611 total
includes taxes & fees
Nov 8 - Nov 9
Wren Retweet- Country Estate in Center of C’Town
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.

18. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is CA $505
CA $823 total
includes taxes & fees
Nov 9 - Nov 10
Turnbridge Manor
A two-story house with a porch, two windows, and a door.

19. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Denton
10.0 out of 10, Exceptional, (15 reviews)
"The house was perfect, welcoming and comfortable, will be coming back again"
United States
Dallas S.
The price is CA $318
CA $496 total
includes taxes & fees
Dec 1 - Dec 2
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Stylish kitchen with open layout and island seating

20. 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 CA $272
CA $653 total
includes taxes & fees
Nov 9 - Nov 10
Pool Loft Suite | Bay Access & Beach Passes
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 vacation rentals that suit your style

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Top Queen Anne's County Hotel Reviews

A two-story house with a porch, a front door, and a small garden area.
The Wildset

The Wildset

The Wildset
Downtown St. Michaels

10/10 Excellent

Our stay at the Wildset was amazing! The room was beautiful and clean. The staff were available at all hours and did the most to ensure our stay was special. The hotel has lots of small touches that truly make the experience like bikes, a cafe with coffee and drinks, and smore's kits in the evenings.
Canada
Mairi
Reviewed August 11, 2026
The Wildset

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 $95 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.