Holiday Homes in Queenstown

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Queenstown

Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Enjoy serene waterfront views and easy access to moorings and facilities.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (227)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Quiet Relaxing Waterfront Suisse Chalet
Guests gather at the ceremony site, surrounded by lush greenery and a serene water view.

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Enjoy cooking in this well-lit kitchen with a central island, wooden cabinetry, and stainless steel appliances.

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (112)
"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Stunning two-story home with a charming entrance, complete with a wreath-adorned door and a cozy porch.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
10.0 out of 10, Exceptional, (24)
"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
Relax by the pool surrounded by lush greenery and vintage bicycles.

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

9.2 out of 10, Wonderful, (25)
"Was the perfect spot for a nice weekend getaway with some friends."
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Enjoy cooking in this well-equipped kitchen with a dishwasher, sink, and range hood.

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

9.4 out of 10, Exceptional, (14)
"Wonderful location and just perfect for our family! "
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Overlooking the marina, the city skyline reflects off the calm water, offering a serene urban experience.

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is AU$506
includes taxes & fees
13 Aug - 14 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Relax by the serene pool surrounded by lush greenery and a comfortable bench.

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

10.0 out of 10, Exceptional, (133)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Guests can enjoy a serene waterfront view from this tranquil pier.

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Cozy Annapolis Cottage
Relax on the outdoor deck surrounded by lush greenery and trees, featuring a sofa set, wicker chair, and small table.

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (13)
"Spent 2 wonderful weeks at this cottage! Very close to walking trail and loop around Naval Stadium. Easy access to shopping dining, highly recommend!!!!"
Cozy Annapolis Cottage
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
Relax by the water's edge, where a row of chairs invites you to unwind and take in the serene views.

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

8.4 out of 10, Very good, (5)
"Relaxing weekend in Annapolis. Enjoyed the quiet and a short walk to the beach"
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
Charming Historic Annapolis Home With Two Off-street Parking Places!
Staircase leads to a warm and inviting interior with a fireplace and wooden door.

Charming Historic Annapolis Home With Two Off-street Parking Places!

10.0 out of 10, Exceptional, (190)
"A very pleasant place to hang out with family. The road traffic was a little bothersome. "
Charming Historic Annapolis Home With Two Off-street Parking Places!
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Stroll up to the charming entrance, where a brick pathway leads to a cozy home with a red door and inviting porch.

Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking

9.8 out of 10, Exceptional, (45)
"Great location to the academy and shopping"
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Relax on Kent Island in 3 Bedroom Home w/Waterview
Overlooking the marina, the city skyline shines brightly.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AU$499
includes taxes & fees
11 Aug - 12 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview
Edgewater/Mayo Gateaway w/ Hot Tub
Fridge, microwave, oven, stovetop

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (19)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
The price is AU$863
includes taxes & fees
18 Aug - 19 Aug
Edgewater/Mayo Gateaway w/ Hot Tub
St. Michaels Waterfront Home
Relax by the serene lake with a dock and a small boat, surrounded by lush greenery and comfortable Adirondack chairs.

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Enjoy a room with a sliding glass door leading to a balcony offering a water view.

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

9.8 out of 10, Exceptional, (16)
"We wanted to celebrate Easter with our two daughters who go to Loyola in Baltimore so we decided to stay in Annapolis area. We absolutely loved the house. The location and view was amazing- right on the Chesapeake bay! The house was clean and welcoming. There were so many nice little touches that made us feel welcomed. We had a great weekend celebrating Easter with our two daughters and son. The house was the perfect size for the 5 of us. "
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Enjoy a meal with a view of the ocean from this dining area with large windows.

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (43)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is AU$469
includes taxes & fees
3 Aug - 4 Aug
BAYSIDE BUNGALOW
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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