Queen Anne's County holiday homes

We found 928 holiday rentals — enter your dates for availability
Select from 89 homes, 14 cottages and other holiday rentals in Queen Anne's County to find one that's perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a fireplace. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Popular Queen Anne's County destinations on Bookabach

Holiday rentals with weekly discounts – Queen Anne's County

Showing deals for:20 Nov - 27 Nov

Exterior Rear of House and Dock
Porch Dining Table
Swimming Pool
Kitchen
Exceptional
(34 reviews)

Waterfront Home near Annapolis, MD

Galesville

8% off
NZ$22,575
for 7 nights, 1 home
NZ$3,225 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Interior
The view off of the point, breathtaking.
Pool
Another view from above.
Exceptional
(45 reviews)

Grandview- Main House

Bozman

25% off
NZ$8,085
for 7 nights, 1 home
NZ$1,155 per night
includes taxes & fees
Grandview- Main House
Exterior
Terrace/patio
Kitchen - Granite Island
The Green Bedroom View
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
NZ$16,949
for 7 nights, 1 home
NZ$2,421 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
View from Pier back to house!
Pool
screened porch
View from Foyer into Great Room
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
NZ$13,762
for 7 nights, 1 home
NZ$1,966 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Sitting area overlooking Burley Creek
Enjoy screened in porch with dining table and sitting area
West-facing screened porch with bar area and café lights for night ambience
Lawn for yard games along the waterfront, or simply relax in the shade
Exceptional
(62 reviews)

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis

8% off
NZ$9,147
for 7 nights, 1 home
NZ$1,307 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Room
Property grounds
Beach
Living area
Exceptional
(92 reviews)

Chesapeake Bay Cottage

Churchton

8% off
NZ$4,131
for 7 nights, 1 cottage
NZ$590 per night
includes taxes & fees
Chesapeake Bay Cottage
Private kitchen
Interior
Exterior
Exterior
Exceptional
(14 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

8% off
NZ$7,173
for 7 nights, 1 home
NZ$1,025 per night
includes taxes & fees
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Interior
Exterior
3rd floor suite; queen and 2 twins; en-suite bath, sitting area, deck access.
Dining
Exceptional
(5 reviews)

Grand home located right on Main St, walk to Chesapeake Bay & great restaurants

Rock Hall

8% off
NZ$9,614
for 7 nights, 1 home
NZ$1,373 per night
includes taxes & fees
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
PUBLIC BEACH/PARK 2 MILES AWAY
SCREENED PORCH
DINING ROOM SEATS 10-14 W/LEAFS
FAMILY ROOM W/FIREPLACE & FLAT SCREEN TV
Exceptional
(45 reviews)

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Annapolis

12% off
NZ$11,290
for 7 nights, 1 home
NZ$1,613 per night
includes taxes & fees
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Dining room
New Kitchen 2022
Interior
Exterior
Exceptional
(64 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
NZ$6,261
for 7 nights, 1 home
NZ$894 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Delightful front garden welcomes you when approaching house from driveway
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Exceptional
(162 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
NZ$3,721
for 7 nights, 1 home
NZ$532 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Property grounds
Living area
Interior
Interior
Exceptional
(15 reviews)

Waterfront 4 BR home with private pier and boat dock

Grasonville

8% off
NZ$9,277
for 7 nights, 1 home
NZ$1,325 per night
includes taxes & fees
Waterfront 4 BR home with private pier and boat dock
Exterior
Private kitchen
Living area
Dining
Excellent
(9 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
NZ$6,103
for 7 nights, 1 home
NZ$872 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Dining
Pool
Living area
Exterior
Exceptional
(57 reviews)

Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!

Annapolis

15% off
NZ$5,765
for 7 nights, 1 home
NZ$824 per night
includes taxes & fees
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
Marina
Terrace/patio
Living room with wood fireplace and second TV with basic channels
upstairs bedroom w/ King size bed and space for queen air mattress
Exceptional
(92 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena

8% off
NZ$6,461
for 7 nights, 1 home
NZ$923 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Separate entryway with electronic keypad.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Local artwork is displayed and for sale, if you wish to take a memory home.
Twin size sofa/futon for a 3rd person.
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

8% off
NZ$2,883
for 7 nights, 1 apartment
NZ$412 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Living area
Dining
Interior
Private kitchen
Exceptional
(10 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
NZ$6,249
for 7 nights, 1 cottage
NZ$893 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Sit and stay a while!
View down the lane
Living Room with flat screen TV and sleeper sofa
Dining Room - Seats 6
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
NZ$3,359
for 7 nights, 1 cottage
NZ$480 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Property grounds
Exterior
Dining
Living area
Exceptional
(20 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman

8% off
NZ$4,999
for 7 nights, 1 cottage
NZ$714 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Light and bright dining room with space for 6 (plus a high chair).
Light and bright dining room with space for 6 (plus a high chair).
Light and bright dining room with space for 6 (plus a high chair).
Comfortable family room with reclining sofa, Smart TV and remote controlled window shades.
Exceptional
(8 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
NZ$5,655
for 7 nights, 1 home
NZ$808 per night
includes taxes & fees
Cozy Cottage with Beach Access
Property grounds
Pool
Interior
Private kitchen
Exceptional
(216 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville

12% off
NZ$5,601
for 7 nights, 1 room
NZ$800 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Exterior detail
Be ready to float! Bring your own inner tubes  and tennis shoes!
Living area
Living area
Exceptional
(143 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
NZ$3,470
for 7 nights, 1 cottage
NZ$496 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Property grounds
Front gardens
Interior
House front
Exceptional
(63 reviews)

Beautiful Retreat Located in Rock Hall - walk to everything!

Rock Hall

13% off
NZ$4,203
for 7 nights, 1 home
NZ$600 per night
includes taxes & fees
Beautiful Retreat Located in Rock Hall - walk to everything!
Living area
Exterior
Exterior
Exterior
Exceptional
(23 reviews)

In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!

Rock Hall

8% off
NZ$2,949
for 7 nights, 1 home
NZ$421 per night
includes taxes & fees
In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!

Find the perfect holiday rental for your Queen Anne's County getaway

Learn about the unique charm of Queen Anne's County with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Queen Anne's County

Are you hoping to discover attractions to visit while you're in the area? Venture out of your holiday home and experience everything that Queen Anne's County has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Queenstown Harbor Golf (6.5 mi / 10.5 km)
  • St. Michaels Winery (19.9 mi / 32 km)
  • Bay Hills Golf Club (22.1 mi / 35.5 km)
  • Maryland Renaissance Festival (28.2 mi / 45.4 km)
  • Paul Reed Smith Guitars (13.8 mi / 22.2 km)
  • Hog Neck Golf Course (15 mi / 24.1 km)

Exploring the natural features in Queen Anne's County

Whether you're an active traveller or just want to take in the scenery, Queen Anne's County is a great place to get out in nature. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Eastern Neck National Wildlife Refuge (8.4 mi / 13.5 km)
  • Chesapeake Bay Environmental Center (10.8 mi / 17.4 km)
  • Northern Chesapeake Bay (15.8 mi / 25.5 km)
  • Sandy Point Beach (17.7 mi / 28.5 km)
  • Bay Ridge Beach (21.9 mi / 35.3 km)
  • Betterton Beach (22.7 mi / 36.6 km)

Frequently asked questions

What is the best area to stay in Queen Annes County when booking a holiday home?
Stevensville is one of the more in-demand areas to find a holiday home in Queen Annes County. Looking for some fun things to see and do here? Take time to visit Matapeake State Park and Love Point State Park.
What is the most popular type of holiday home accommodation in Queen Annes County?
Based on our data, houses are the most in-demand property type in Queen Annes County. But that goes without saying, everyone's idea of an awesome trip isn't going to be the same. Bookabach has holiday homes with every size, shape and budget in mind, and we'll help you locate the perfect match.
How much does it cost to rent a holiday home in Queen Annes County?
Length of stay, property type and time of year are among the factors that can determine the price of a holiday home. Simply add your travel dates to find your perfect match. From cosy cabins to sprawling luxury villas, all Bookabach holiday homes provide incredible value.
How much does it cost to rent a beach house in Queen Annes County?
The average price for a holiday home by the beach in Queen Annes County depends on when you're visiting the area and the size and style of property you're looking for. You can quickly and easily find prices on Bookabach by entering your travel dates. Then use the handy filter tool to select the number of bedrooms and amenities important to you, like WiFi, a pool and air conditioning.
What are popular home amenities in Queen Annes County?
When it comes to home amenities that people search for in Queen Annes County, a microwave oven, a dryer and a fridge are at the top of the list. With Bookabach holiday homes, you'll have options to suit your taste and style, whether you're on a trip with friends, relatives or even pets.
Are there large group holiday homes in Queen Annes County?
Take your pick of 20 holiday homes in Queen Annes County that can sleep 10 or more guests. Whether you're organising a family trip or a special event, there's plenty of room to get your loved ones together under one roof.
What are the top attractions for families in Queen Annes County?
Keep the kids amused at these popular family-friendly attractions in Queen Annes County:
  • Queenstown Premium Outlets
  • Queenstown Harbour Golf Club
  • Chesapeake Bay Environmental Centre
Can I find two-bedroom holiday homes in Queen Annes County?
Select from seven two-bedroom properties in Queen Annes County. Put your little ones in the second room or maybe fill it with a couple of your nearest and dearest friends. There's plenty of space for whoever's fortunate enough to be coming along for the ride.
Are there holiday homes with WiFi in Queen Annes County?
You can choose from 42 holiday homes with WiFi in Queen Annes County. If you'd like to disconnect from daily life while on holiday, but still want to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How old do you have to be to rent a holiday home in Queen Annes County?
The minimum age is usually 16, 18 or 21. It can change from one property to another on Bookabach, so check the rules of your preferred Queen Annes County stay before making a booking.
How long can I rent a holiday home in Queen Annes County for?
It's down to the Queen Annes County property. To look at a list of options offering extended stays, simply type your dates and number of people into Bookabach's search page. You can look forward to having the whole place to yourself, along with amenities such as a fully-equipped kitchen, air conditioning and a yard where the kids can play. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.

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