Photo by KM Moore

Queen Anne Holiday Rentals

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Check prices for these dates

Tonight
20 Jan - 21 Jan
Tomorrow
21 Jan - 22 Jan
This weekend
24 Jan - 26 Jan
Next weekend
31 Jan - 2 Feb

Holiday Rentals in Queen Anne

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

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

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Miscellaneous

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.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (113)
"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (75)
"Nice location down town. House was just as the pictures showed. "
Walk to Everything House
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (78)
"Very clean, excellent communications,"
The price is AU$258
includes taxes & fees
22 Jan - 23 Jan
First Floor Studio Apartment in Historic Chestertown
Circa 1700 Chesapeake Colonial home on the National Register.
Exterior

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (50)
"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."
Circa 1700 Chesapeake Colonial home on the National Register.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (172)
"This house was in the perfect location, central to everything in St. Michaels. I wish the furniture was more comfortable in the shared spaces for hanging out, but overall a wonderful weekend with friends. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is AU$439
includes taxes & fees
21 Jan - 22 Jan
BAYSIDE BUNGALOW
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Interior

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (32)
"Beautiful home, beautiful property! My family meets up annually and the house fit us perfectly. Plenty of room to spread out and congregate together. The home also provides so much to do with all the amenities! Thanks for the memories "
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Cass-N-Reel Luxury Houseboat
Smart TV

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
The price is AU$477
includes taxes & fees
23 Jan - 24 Jan
Cass-N-Reel Luxury Houseboat
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (33)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool

Pool and Bay Views on wrap around deck in Kent Island

9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (220)
"This was a winter getaway to a very comfortable house with all the amenities on a quiet tributary of the Chesapeake. A rare vacation for and just what we wanted. Conveniently located near St Michael’s and Easton. Communication was excellent and everything was just as described. Would go back if we get the opportunity. "
Relaxing Waterfront Cottage Near St Michaels, Maryland
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Beach

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

10.0 out of 10, Exceptional, (21)
"Convenient to restaurants and a warm, comfortable place to gather and relax after a hard, cold waterfowl hunt"
The price is AU$388
includes taxes & fees
21 Jan - 22 Jan
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
Miscellaneous

Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

8.8 out of 10, Excellent, (11)
"The location is spectacular with expansive views of the Chesapeake Bay and the Bay Bridge. The house itself is immaculate and had lots of space for our family. I would imagine it's even better in the summer when the pool is available.One caution: the playhouse is really cool but not a place to let younger kids play unsupervised."
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (33)
"Clean, Spacious, and exactly as advertised! "
The price is AU$438
includes taxes & fees
2 Feb - 3 Feb
Relax on Kent Island in 3 Bedroom Home w/Waterview
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (47)
"Nice place "
Dollhouse in Central Historic St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (116)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Outdoor pool

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
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 types of properties in Queen Anne you may be interested in

Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (472)
"Upscale facility with caring and attentive staff that go above and beyond to make you feel welcomed and comfortable. "
The price is AU$228
includes taxes & fees
2 Feb - 3 Feb
Hyatt Place Kent Narrows & Marina
St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Enjoyed the stay. It was close to town and a lot of great attractions "
The price is AU$169
includes taxes & fees
22 Jan - 23 Jan
St Michaels Inn
Inn at Perry Cabin
Breakfast, lunch, dinner served; sea views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (328)
"The property is beautiful and, the atmosphere is relaxing. I loved the fresh floral Christmas decorations."
The price is AU$615
includes taxes & fees
5 Feb - 6 Feb
Inn at Perry Cabin
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.

Frequently asked questions

Can I find holiday rentals in Queen Anne?

Yes, there are holiday rentals close to the most popular sights in Queen Anne, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Queen Anne has to offer?

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.: This holiday home rental outside of Queen Anne is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 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 patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Queen Anne?

Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Tuckahoe State Park. In the wider area, you’ll find Wye Landing and Hog Neck Golf Course.

What are holiday rentals like in Queen Anne?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Queen Anne. Holiday rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.