A calm lake surrounded by dense green trees.

Queenstown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Queenstown vacation rentals

Interior

1. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
The price is ￥14,408
￥48,587 total
includes taxes & fees
Sep 3 - Sep 4
Cass-Away Luxury Houseboat
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is ￥18,827
￥48,559 total
includes taxes & fees
Sep 2 - Sep 3
Charming Coastal/Country Home w/3 Acres & Sauna!
Dining

3. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is ￥40,023
￥67,879 total
includes taxes & fees
Sep 1 - Sep 2
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

4. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is ￥13,448
￥43,945 total
includes taxes & fees
Sep 1 - Sep 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach

5. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥18,859
￥46,081 total
includes taxes & fees
Sep 1 - Sep 2
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (124 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is ￥15,849
￥25,429 total
includes taxes & fees
Sep 2 - Sep 3
First Floor Studio Apartment in Historic Chestertown
Exterior detail

7. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥32,018
￥50,534 total
includes taxes & fees
Sep 1 - Sep 2
BAYSIDE BUNGALOW
Living area

8. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥37,141
￥69,236 total
includes taxes & fees
Oct 1 - Oct 2
Bayside Cottage steps from Rock Hall Harbor
Interior

9. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 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 ￥47,707
￥60,252 total
includes taxes & fees
Sep 2 - Sep 3
Family Retreat at Lansdowne Manor
Interior

10. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is ￥22,333
￥54,112 total
includes taxes & fees
Sep 1 - Sep 2
Large 2 bedroom house with private parking in a nice neighborhood
Living area

11. 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 ￥29,393
￥45,219 total
includes taxes & fees
Sep 1 - Sep 2
Secluded Cottage in Middle of Chestertown
Private kitchen

12. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 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 ￥30,833
￥78,039 total
includes taxes & fees
Sep 1 - Sep 2
Pool Loft Suite | Bay Access & Beach Passes
Pool

13. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is ￥35,300
￥68,895 total
includes taxes & fees
Sep 1 - Sep 2
Waterfront Oasis of Annapolis Star
Living area

14. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥36,020
￥56,544 total
includes taxes & fees
Sep 1 - Sep 2
Newly restored apartment in the heart of Chestertown
Living area

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is ￥30,257
￥46,327 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Marina

16. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is ￥30,656
￥81,486 total
includes taxes & fees
Sep 1 - Sep 2
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Terrace/patio

17. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Chris A.
The price is ￥32,106
￥71,458 total
includes taxes & fees
Sep 1 - Sep 2
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Terrace/patio

18. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is ￥12,391
￥41,318 total
includes taxes & fees
Sep 13 - Sep 14
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Private kitchen

19. Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Property grounds

20. 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 ￥51,350
￥80,109 total
includes taxes & fees
Sep 1 - Sep 2
Wren Retweet- Country Estate in Center of C’Town
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 Queenstown Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean room ,nice helpful staff and the shuttle service was 👍 great"
mona 1-night trip
Posted 6 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Queenstown

Search for holiday rentals in Queenstown on Expedia! You can easily find your home rentals, villas, holiday apartments in Queenstown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Queenstown!

Frequently asked questions

Are there vacation rentals in Queenstown?

Yes, we have vacation rentals in Queenstown near Rufus M and Loraine Hall Todd Performing Arts Center, or you can select a more remote option if you want a relaxing stay. Queenstown is known for its restaurants and golf courses. Make sure you have time to check out the shopping while you're in the area.

What's the top vacation rental in Queenstown?

Relax on Kent Island in a 4 Bedroom Home w/Waterview!: You might want to consider this vacation home rental near Queenstown, which offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Queenstown?

Expedia has 7 vacation rentals for your stay in Queenstown.

What’s there to see and do in Queenstown?

Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Eastern Neck National Wildlife Refuge. While here, Queenstown Premium Outlets and Queenstown Harbor Golf are other places worth a visit.

What’s a vacation rental in Queenstown like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Queenstown. Vacation rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.