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Queen Anne's County Holiday Rentals

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Top Cities in Queen Anne's County

Holiday RentalsHoliday Rentals

Stevensville

Stevensville

Top Holiday Rentals Destinations in Queen Anne's County

Marina
Floating 2 bed 2 bath condo stunning views of the bay

Houseboat in Stevensville

2.0 star property
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Holiday Home in Stevensville

10.0 out of 10, Exceptional, (15)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."
United States
Kerrith D.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Marina
Cass-N-Reel Luxury Houseboat

Houseboat in Grasonville

10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Holiday Home in stevensville

10.0 out of 10, Exceptional, (197)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."
United States
David N.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Fridge, microwave, stovetop, dishwasher
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Holiday Home in Chester

10.0 out of 10, Exceptional, (126)
"This house was charming and comfortable. The view was spectacular. Neighbors and friendly. The whole place has a serene feel to it. In addition, the owners were very helpful and responsive. We will be back again!"
United States
Sue R.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Exterior
Circa 1700 Chesapeake Colonial home on the National Register.

Holiday Home in Stevensville

9.8 out of 10, Exceptional, (57)
"What a stunning place, we were delighted by this 300 year old property, the view was incredible. "
United States
Karen N.
Circa 1700 Chesapeake Colonial home on the National Register.
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home in Stevensville

9.8 out of 10, Exceptional, (42)
"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 NZ$440
includes taxes & fees
11 Dec - 12 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Interior
40' Bristol sailboat with spectacular views

Houseboat in Stevensville

2.0 star property
40' Bristol sailboat with spectacular views
Property grounds
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Holiday Home in Pasadena

9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
United States
Armando V.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

Mobile Home in Edgewater

10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
Waterfront Getaway, Dock Your Boat & Play!
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is NZ$1,151
includes taxes & fees
8 Dec - 9 Dec
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Holiday Home in Glen Burnie

8.6 out of 10, Excellent, (8)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
The price is NZ$602
includes taxes & fees
8 Dec - 9 Dec
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Smart TV, fireplace
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Holiday Home in Glen Burnie

8.0 out of 10, Very good, (2)
"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"
United States
James D.
The price is NZ$217
includes taxes & fees
7 Dec - 8 Dec
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Fridge, microwave, oven, stovetop
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Holiday Home in Historic District

9.4 out of 10, Exceptional, (19)
"Great place, excellent location!"
United States
Joseph C.
The price is NZ$2,060
includes taxes & fees
8 Dec - 9 Dec
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Holiday Home in Tracys Landing

9.8 out of 10, Exceptional, (50)
"Our week at Jacob's property was excellent. It was the perfect location for a family getaway, and Jacob was helpful and responsive."
United States
Brett F.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Holiday Home in Cambridge

9.8 out of 10, Exceptional, (7)
"Wow! What an incredible property and house. We were a group of families with small kids, and it was heaven for them playing in the pool, on the dock, on the playground, and in the expansive yard. Lots of beautiful sunsets on the patio for the grown-ups too. We never had to leave. Can't recommend highly enough. "
United States
Lea F.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Outdoor dining
BAYSIDE BUNGALOW

Holiday Home in Rock Hall

10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$523
includes taxes & fees
1 Jan - 2 Jan 2026
BAYSIDE BUNGALOW
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Cottage in Earleville

9.8 out of 10, Exceptional, (59)
"Lovely cottage, well-equipped, immaculately clean. "
United States
Mary
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Exterior
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Holiday Home in Murray Hill

2.5 star property
10.0 out of 10, Exceptional, (34)
"Absolutely perfect! Will stay again!!"
United States
Brian
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is NZ$275
includes taxes & fees
8 Dec - 9 Dec
First Floor Studio Apartment in Historic Chestertown
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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Top Queen Anne's County Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"The room was great, but the staff is where this place shines. They were great!"
Ann 2-night trip
Posted 1 day ago
Hampton Inn Baltimore/Glen Burnie

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 favorite 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 depends 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 selected for you start as low as NZ$217 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.