A calm lake surrounded by dense green trees.

Queenstown Holiday Rentals

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Our top choices for Queenstown holiday rentals

1. 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 NZ$708
includes taxes & fees
17 Sept - 18 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

2. 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 NZ$524
includes taxes & fees
20 Aug - 21 Aug
BAYSIDE BUNGALOW

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (122 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is NZ$269
includes taxes & fees
31 Aug - 1 Sept
First Floor Studio Apartment in Historic Chestertown

4. 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)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is NZ$559
includes taxes & fees
17 Sept - 18 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!

5. 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 traveller
The price is NZ$580
includes taxes & fees
20 Aug - 21 Aug
Newly restored apartment in the heart of Chestertown

6. 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 NZ$479
includes taxes & fees
20 Aug - 21 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

7. 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, (76 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is NZ$2,389
includes taxes & fees
15 Sept - 16 Sept
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

8. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is NZ$2,382
includes taxes & fees
16 Sept - 17 Sept
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

9. 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, (53 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is NZ$551
includes taxes & fees
31 Aug - 1 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

10. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (3 reviews)
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United States
Maria S.
The price is NZ$1,959
includes taxes & fees
30 Aug - 31 Aug
Waterfront Escape with Pool Nature Lover Paradise

11. 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 NZ$717
includes taxes & fees
17 Sept - 18 Sept
Bayside Cottage steps from Rock Hall Harbor

12. 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 NZ$703
includes taxes & fees
2 Sept - 3 Sept
Family Retreat at Lansdowne Manor

13. 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, (13 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is NZ$1,226
includes taxes & fees
24 Aug - 25 Aug
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

14. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (15 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is NZ$1,030
includes taxes & fees
20 Aug - 21 Aug
Turnbridge Manor

15. 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 NZ$814
includes taxes & fees
1 Sept - 2 Sept
Wren Retweet- Country Estate in Center of C’Town

16. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is NZ$1,094
includes taxes & fees
25 Aug - 26 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

17. 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 NZ$663
includes taxes & fees
20 Aug - 21 Aug
Waterfront Oasis of Annapolis Star

18. 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 NZ$475
includes taxes & fees
20 Aug - 21 Aug
Secluded Cottage in Middle of Chestertown

19. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful property and very clean with full amenities. We had a wonderful day. Thank you for everything."
United States
David S.
The price is NZ$1,167
includes taxes & fees
20 Aug - 21 Aug
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

20. 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 NZ$853
includes taxes & fees
30 Aug - 31 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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

Find out more about Queenstown

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Queenstown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Queenstown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Queenstown. Seeing all the best attractions is bound to make you fall in love with Queenstown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Queenstown short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there holiday rentals in Queenstown?

Yes, there are holiday rentals in Queenstown close to Rufus M and Loraine Hall Todd Performing Arts Center, or you can select a more secluded option if you're looking for 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 are some of the best holiday rentals that Queenstown has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Queenstown is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Queenstown?

Expedia has 6 holiday 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 holiday rental in Queenstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Queenstown. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family trips.