Queen Anne's Area, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Queen Anne's Area, Maryland on RentalSaver.com!

Queen Anne's Area Rentals

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From $707 per night (USD)
VRBO
Caribbean HEATED POOL Home near Matapeake Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: This exquisite Eastern Shore residence is perfect for relaxation and a quick trip to the beach or Annapolis, bo ...
From $707 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Chic 3 BR / 2 BA Cottage Near Chesapeake Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Plan your getaway on the Chesapeake Bay! Blue Heron’s Landing is on beautiful Kent Island, MD. The home is a short walk ...
From $342 per night (USD)
VRBO
$Chessie Cottage-Chesapeake Bay\nGreat views from easy single floor living!$
From $716 per night (USD)
VRBO
Chessie Cottage-Chesapeake Bay\nGreat views from easy single floor living!
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
Welcome to Chessie Cottage on The Bay! There is an intangible quality to a cottage coming from a unique combination of ...
From $716 per night (USD)
VRBO
From $567 per night (USD)
VRBO
Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Escape to the shores of Kent Island at this 3-bedroom home, just minutes from historic Annapolis and under 2 ho ...
From $567 per night (USD)
VRBO
From $252 per night (USD)
VRBO
Floating 2 bed 2 bath condo stunning views of the bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
A truly unique experience, Enjoy the stunning view of the bay and nature staying on this 40 ft yacht moored at a fishing ...
From $252 per night (USD)
VRBO
From $821 per night (USD)
Expedia
Private Peaceful Waterfront House with Pool & Hot Tub
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Family owned beautiful waterfront home with a fully stocked kitchen, dining room, master bedroom and large living areas. ...
From $821 per night (USD)
Expedia
From $484 per night (USD)
VRBO
Welcome to The Blue Crab House Stevensville Maryland Eastern Shore
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome To The Blue Crab House Full of your finest eastern shore charm in Stevensville Maryland this spacious 3 bedroo ...
From $484 per night (USD)
VRBO
From $199 per night (USD)
VRBO
Room for an Island getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy easy access to everything from this perfectly located room with water views off of Rt. 50 between the Chesapeake B ...
From $199 per night (USD)
VRBO
From $267 per night (USD)
VRBO
River Cottage, Chestertown
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Relax on the scenic Eastern Shore. We are located just off the Chester River. Step away from the hustle and bustle to ou ...
From $267 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Anchors Away!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar exp ...
From $446 per night (USD)
VRBO
From $684 per night (USD)
VRBO
Kent Island Waterfront | Pool | Stunning View
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Relax and unwind. Located on the Chesapeake Bay, this charming vacation rental features 3 bedrooms, 2 bathrooms, and a r ...
From $684 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Get ready to relax in this brilliant 3-bedroom coastal-country home in Stevensville. Remodeled and refurnished complete ...
From $318 per night (USD)
Expedia
From $572 per night (USD)
VRBO
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Bay Creek Cottage! We are excited to have you as guests and hope you enjoy your vacation on Kent Island! Plea ...
From $572 per night (USD)
VRBO
From $464 per night (USD)
Expedia
One-level waterfront home with beach and stunning views all the way to the Bay Bridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stunning views and your own sandy beach! Relax with the whole family as you watch the world sail by from the comfort of ...
From $464 per night (USD)
Expedia
From $689 per night (USD)
VRBO
Pet-Friendly Home on Chester River w/ Dock!
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Ideal for Goose & Deer Hunting Trips | Kayaks Provided | Crab Traps Calling all outdoor explorers! Lower your anchor at ...
From $689 per night (USD)
VRBO
From $1455 per night (USD)
Expedia
Guest Lodge | Private Pool | Outdoor Dining | Game Room
Bedrooms:
3
Bathrooms:
7
Sleeps:
25
Welcome to your dream escape. A one-of-a-kind Eastern Shore Gentleman's Farm that embodies elegance and tranquility. T ...
From $1455 per night (USD)
Expedia
From $1042 per night (USD)
VRBO
Spacious luxury home in charming Downtown Chestertown/Pets Welcome/Free Wifi
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Experience the charm of Chestertown, Maryland by indulging in a stay at our upscale vacation residence. Located just a s ...
From $1042 per night (USD)
VRBO
From $498 per night (USD)
VRBO
Charming 2-bedroom first floor apartment in Chestertown with Cute Outdoor Space!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This modern luxury unit boasts a first-floor apartment with two bedrooms, full access to a private back patio/outdoor sp ...
From $498 per night (USD)
VRBO
From $619 per night (USD)
VRBO
Modern Lux Upstairs apt in Chestertown/Family Friendly/Walk to Shops and Dining!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Experience the charm of Chestertown, Maryland by indulging in a stay at our upscale vacation residence. Located just a s ...
From $619 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the beauty of Kent Island from this 3-bedroom house. This fantastic property offers a king bed, a queen bed, an ...
From $458 per night (USD)
Expedia
From $422 per night (USD)
VRBO
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Remodeled in 2023, this light-filled, 2-story private home offers 2,100 sqft of stylish comfort—perfect for a relaxing g ...
From $422 per night (USD)
VRBO
From $613 per night (USD)
VRBO
Pier Pleasure Retreat- Waterfront & Private Pier
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Pier Pleasure Retreat: Your Waterfront Oasis Welcome to Pier Pleasure Retreat, a newly renovated 4-bedroom, 4-bathroom ...
From $613 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy the peace and tranquility at "Outrange," Blue Heron Farm's recently updated cabin. While we are new to VRBO, we h ...
From $245 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Blue Heron Farm Waterfront Chalet
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of ...
From $360 per night (USD)
Expedia
From $129 per night (USD)
VRBO
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Wye Mills is waiting for you at this awesome 1-bedroom cottage. With WiFi, heating, a washing machine, and more, guests ...
From $129 per night (USD)
VRBO
From $556 per night (USD)
Expedia
RELAX- Eastern Shore Creek Home - 6 Guests
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Come enjoy the coastal lifestyle of the Chesapeake Bay with friends & family! **Located in the Prospect Bay Country Clu ...
From $556 per night (USD)
Expedia
From $1220 per night (USD)
VRBO
Kent Island Waterfront | Game Room | Private Dock | Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Soar above the everyday. Vacation like a legend. This waterfront oasis in Queen Anne's County offers an escape that ble ...
From $1220 per night (USD)
VRBO
From $169 per night (USD)
Expedia
Chesapeake Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
VERY CLOSE to Island wedding venues. Cottage is a private detached 1st floor dwelling and has off street parking. Queen ...
From $169 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Historic luxury townhouse in the heart of downtown Chestertown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Historic Luxury Townhouse on High Street – Heart of Downtown Chestertown Welcome to 125 High Street—an exquisitely reno ...
From $389 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Discover this lovely 2 bedroom and loft gem in Chestertown. This welcoming apartment features 3 queen beds, perfect for ...
From $253 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful Kent Island Getaway with Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a bonus room for all your family entertaining. You will lov ...
Click For Pricing
VRBO
From $632 per night (USD)
Expedia
NEW Spacious 5BDR house on serene Kent Island - close to all the hot spots!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to your serene escape on the beautiful shores of Love Point in Stevensville, MD! This spacious 5-bedroom, 3.5-b ...
From $632 per night (USD)
Expedia
From $513 per night (USD)
VRBO
River Heights Retreat with heated pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The cottage has lovely water views from the full kitchen, living room, and a stunning luxurious first floor master suite ...
From $513 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming 3BR/2BA Home on 1 Acre – Peaceful Escape Near Beaches & Trails Escape to comfort and tranquility in this beaut ...
From $330 per night (USD)
Expedia
From $1570 per night (USD)
VRBO
On-Site Boat Dock: Queenstown Home w/ Pool & Yard!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Expansive Outdoor Relaxation Space | Sunroom w/ Views | Pet Friendly w/ Fee Dive into waterfront fun when you stay at t ...
From $1570 per night (USD)
VRBO
From $555 per night (USD)
VRBO
Waterfront House: Hot Tub, Fire Pit, & Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Escape to a stunning Waterfront Getaway on Maryland's Eastern Shore! This charming house offers breathtaking wa ...
From $555 per night (USD)
VRBO
From $634 per night (USD)
VRBO
Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Charming Kent Island Retreat – 4 BR • 2.5 BA • Pool Table • Near the Water ""Brand New Construction"" Escape to the East ...
From $634 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
• Embrace historic charm in our exquisitely renovated third-floor walk-up, located in a beautiful historic building in t ...
From $313 per night (USD)
Expedia
From $460 per night (USD)
VRBO
Crab Alley | Waterfront Home + Hot Tub + Game Room
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
BNB Breeze Presents: Crab Alley Welcome to Crab Alley, a stunning Bayfront home nestled in the serene surroundings of Ch ...
From $460 per night (USD)
VRBO
From $805 per night (USD)
Expedia
Kent Island Maryland Getaway
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Wade a Minute Chester Escape to a charming waterfront retreat located in Chester, MD, this impressive 5-bedroom, 3.5 ba ...
From $805 per night (USD)
Expedia
From $544 per night (USD)
VRBO
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This newly renovated historic home leaves nothing to be desired. Between the beautiful decor, amenities, and location th ...
From $544 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Waterfront condo. Completely renovated. Walk to Kent Island's best places
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Invited to a Kent Island wedding or event -- going to a boat show or Navy football game? This waterfront condo is the pe ...
From $344 per night (USD)
Expedia
From $440 per night (USD)
VRBO
Comfortable 5 Bedroom Waterfront Home on Chesapeake Bay
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
This spacious and comfortable home on the Chesapeake Bay is the perfect location for a family vacation, reunion, or acco ...
From $440 per night (USD)
VRBO

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Queen Anne's Area Rentals

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Results: 143 Rentals