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Compare 657 Vacation Homes in Queenstown with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (211)
"Everything was just as advertised!! Very charming house in a perfect location. Wonderful gas fireplace in the living room, cute back patio, everything we needed and more! This house was absolutely spotless!! A to the cleaning people!! John was a wonderful host! Went out of his way to check on us and offer any assistance if we needed it. We "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (182)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

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

9.6 out of 10, Exceptional, (27)
"Nice and peaceful stay for a quick local getaway. "
The price is AED 377
AED 1,022 total
includes taxes & fees
22 Apr - 23 Apr
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (35)
"Great wx and weekend visit to the Naval Academy. Walking distance to everything and neighborhood was a nice getaway from main street "
Historic Annapolis Home 1.5 blocks from center of town.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (34)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

2.5 star property
10.0 out of 10, Exceptional, (5)
"A great location and plenty of room for visiting groups to be in and out. Clean and well provisioned. Parking was a great feature as well."
Steps to USNA Gate 3 at historic Gatehouse, on-site parking

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (196)
"great time"
PERFECT LOCATION in the heart of history

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

10.0 out of 10, Exceptional, (1)
"As advertised. Great views, dock and decks. Inside is modern, functional and very clean. No complaints whatsoever."
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Clean, Spacious, and exactly as advertised! "
The price is AED 353
AED 1,009 total
includes taxes & fees
20 Apr - 21 Apr
Relax on Kent Island in 3 Bedroom Home w/Waterview

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AED 716
AED 1,394 total
includes taxes & fees
18 Apr - 19 Apr
The Cottage

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (47)
"Our stay was incredible! The house is beautiful, it is super spacious with tons of perfect places to congregate and hang out. The rooms were all extremely comfortable and the beds had high quality mattresses that made sleeping so enjoyable. The views and sunsets were spectacular and our group loved spending our evenings enjoying the hot tub. The house’s location is perfect as it is not only right on the water but it’s just under one mile from the (albeit super tiny) town of Rock Hall. I’d love...
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (40)
"Our group of longtime friends from different states wanted a convenient location to meet for a weekend getaway. The Eastern Shore was a good location and this property was a wonderful and comfortable place for our group. The house was spacious and had plenty of areas for members of the group to enjoy all together or in smaller conversation groups. Our group meals were easy to prepare in the large and well-equipped kitchen. The dining room easily accommodated our group for our dinners and the...
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (16)
"Loved the house, we were glad to be able to book it on short notice for a large group! Beds were insanely comfortable, and the house had everything we needed. It was clean, comfortable, and a fantastic location. Only downside is that the common areas (living room/kitchen/dining area) are a bit small if you have a larger group (8). Overall a great stay and would stay again!!"
7 mins away from Downtown Annapolis

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.6 out of 10, Exceptional, (15)
"This property is perfect for a weekend getaway. The location is unbeatable, and the house is amazing! Clean, well-appointed and beautiful. The property manager was also wonderful to work with. You won't be disappointed."
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (85)
"Gorgeous views and surroundings"
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Walk to Everything House

10.0 out of 10, Exceptional, (78)
"Great location. Loved being near town and the Blue Crab. "
Walk to Everything House

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (110)
"I visited my midshipman and I couldn’t have asked for a better place! Very comfortable & spacious-yet not too big. It was as if we were home. Location was awesome. Mike was great with immediate communication-especially in preparing us with info well before our check in day! I would definitely stay here again! "
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (58)
"We had a wonderful stay at this property and would return in the future. Thank you!"
Recently Renovated Annapolis Home - Conveniently Located
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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Other property types in Queenstown

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

10.0 out of 10, Exceptional, (211)
"Everything was just as advertised!! Very charming house in a perfect location. Wonderful gas fireplace in the living room, cute back patio, everything we needed and more! This house was absolutely spotless!! A to the cleaning people!! John was a wonderful host! Went out of his way to check on us and offer any assistance if we needed it. We "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (23)
"Our weekend stay at Julia’s Arc was truly the perfect weekend!!! The location is perfect and the boat is so clean, cozy, beautifully decorated, and generously stocked. We felt so calm and happy during our whole stay. The top deck is a perfect spot to have a cup of coffee or watch the sunset. Plus, the host, Julia was so accommodating and sweet. We really hope to go back soon! "
Chesapeake Houseboat Getaway on Kent Island, Maryland

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (182)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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.