Queen Anne's County holiday rentals

We found 928 holiday rentals — enter your dates for availability
Select from 87 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 Stayz

Holiday rentals with weekly discounts – Queen Anne's County

Showing deals for:6 Nov - 13 Nov

Kitchen
Kitchen
Kitchen
Exterior
Exceptional
(27 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

12% off
AU$3,368
for 7 nights, 1 room
AU$481 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Outdoor dining
Private kitchen
Room
Dining
Exceptional
(20 reviews)

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis

16% off
AU$7,610
for 7 nights, 1 home
AU$1,087 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
The Green Bedroom View
Terrace/patio
Great Room
Exterior
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
AU$14,442
for 7 nights, 1 home
AU$2,063 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Upstairs Hall
Porch Dining Table
Swimming Pool
Kitchen
Exceptional
(33 reviews)

Waterfront Home near Annapolis, MD

Galesville

8% off
AU$19,129
for 7 nights, 1 home
AU$2,733 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
View from Pier back to house!
Pool
Dining table- seats 10!
screened porch
Exceptional
(145 reviews)

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

Easton

8% off
AU$11,192
for 7 nights, 1 home
AU$1,599 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Exterior
Interior
Exterior
Interior
Exceptional
(13 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

8% off
AU$6,014
for 7 nights, 1 home
AU$859 per night
includes taxes & fees
Charming Home located minutes from the Naval Academy and Downtown Annapolis
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Delightful front garden welcomes you when approaching house from driveway
Exceptional
(161 reviews)

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

Sherwood

10% off
AU$3,150
for 7 nights, 1 home
AU$450 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Exterior
Pool
Interior
Living area
Exceptional
(228 reviews)

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis

8% off
AU$4,635
for 7 nights, 1 home
AU$662 per night
includes taxes & fees
Stunning Waterfront Cottage in the Sailing Capital of the World!
Room
Quiet, tree-filled neighborhood. The apartment is above the garage.
Separate entryway with electronic keypad.
Twin size sofa/futon for a 3rd person.
Exceptional
(20 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

7% off
AU$2,497
for 7 nights, 1 apartment
AU$357 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Exterior
Private kitchen
Dining
Living area
Excellent
(8 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
AU$5,105
for 7 nights, 1 home
AU$729 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Property grounds
Living area
Interior
Room
Exceptional
(14 reviews)

Waterfront 4 BR home with private pier and boat dock

Grasonville

8% off
AU$7,363
for 7 nights, 1 home
AU$1,052 per night
includes taxes & fees
Waterfront 4 BR home with private pier and boat dock
Dining
Pool
Living area
Exterior
Exceptional
(56 reviews)

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

Annapolis

16% off
AU$4,790
for 7 nights, 1 home
AU$684 per night
includes taxes & fees
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
Living Room with flat screen TV and sleeper sofa
View down the lane
Dining Room - Seats 6
Custom kitchen
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,866
for 7 nights, 1 cottage
AU$409 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Living room with wood fireplace and second TV with basic channels
Terrace/patio
Marina
outdoor space
Exceptional
(91 reviews)

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

Pasadena

8% off
AU$5,351
for 7 nights, 1 home
AU$764 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Dining room
New Kitchen 2022
Exterior
Property grounds
Exceptional
(64 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
AU$5,346
for 7 nights, 1 home
AU$764 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Living Room
Kitchen
Family Room
Coffee Station
Exceptional
(89 reviews)

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown

17% off
AU$3,176
for 7 nights, 1 home
AU$454 per night
includes taxes & fees
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Private kitchen
Dining
Private kitchen
Living area
Exceptional
(10 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$4,729
for 7 nights, 1 cottage
AU$676 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Water view from the kitchen
Property grounds
Private kitchen
Dining
Exceptional
(29 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
AU$6,851
for 7 nights, 1 home
AU$979 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Living area
Be ready to float! Bring your own inner tubes and tennis shoes!
Living area
Interior
Exceptional
(143 reviews)

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

Bozman

12% off
AU$2,938
for 7 nights, 1 cottage
AU$420 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
kitchen
Outdoor dining
dining area
Marina
Exceptional
(37 reviews)

This is truly a Baydream!

Rock Hall

8% off
AU$2,954
for 7 nights, 1 home
AU$422 per night
includes taxes & fees
This is truly a Baydream!
Private kitchen
Pool
Interior
Property grounds
Exceptional
(214 reviews)

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

Stevensville

12% off
AU$4,698
for 7 nights, 1 room
AU$671 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Exterior
Exterior
Aerial view
Exterior
Exceptional
(23 reviews)

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

Rock Hall

8% off
AU$2,493
for 7 nights, 1 home
AU$356 per night
includes taxes & fees
In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!
Dining
Exterior
Private kitchen
Living area
Exceptional
(19 reviews)

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

Tilghman

8% off
AU$4,154
for 7 nights, 1 cottage
AU$593 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Interior
Front gardens
Private kitchen
Property grounds
Exceptional
(62 reviews)

Beautiful Retreat Located in Rock Hall - walk to everything!

Rock Hall

13% off
AU$3,137
for 7 nights, 1 home
AU$448 per night
includes taxes & fees
Beautiful Retreat Located in Rock Hall - walk to everything!

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)
  • Crow Farm and Vineyard (20.5 mi / 33 km)
  • Bay Hills Golf Club (22.1 mi / 35.5 km)
  • Maryland Renaissance Festival (28.2 mi / 45.4 km)
  • South River Golf Links (28.5 mi / 45.8 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. Stayz 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 Stayz 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 Stayz 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 Stayz 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 Stayz.
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 Stayz, 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 Stayz'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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