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 $295 per night (USD)
VRBO
KENT ISLAND - Everything The Narrows has to offer you!
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Welcome to our exquisite two-story retreat on Kent Island, designed to captivate with its modern allure and exclusive fe ...
From $295 per night (USD)
VRBO
From $345 per night (USD)
Expedia
Chester River Waterfront Cottage (Love Point Bay)
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private 2 bedroom 1 bathroom waterfront cottage on the Chester River. Enjoy the solitude that this property offers, incl ...
From $345 per night (USD)
Expedia
From $699 per night (USD)
VRBO
Love Point Luxury Waterfront
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Get away from the city and enjoy the waterfront views from the property that is nestled down a private road. Perfect for ...
From $699 per night (USD)
VRBO
From $700 per night (USD)
Expedia
Queenstown Waterfront | Boat Ramp | Pool | Private Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
This 3,600 square foot, 4-bedroom, 3.5-bathroom Wye River waterfront was designed with your comfort in mind, the open fl ...
From $700 per night (USD)
Expedia
From $1700 per night (USD)
VRBO
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Imagine waking up to a back and front yard nature surrounded by pine trees and a Olympic pool. Home with all glass door ...
From $1700 per night (USD)
VRBO
From $619 per night (USD)
VRBO
River Lodge, Casual Riverfront setting
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
The River Lodge sits on the scenic Chester River located 5 miles outside of Chestertown. It's the perfect little get ...
From $619 per night (USD)
VRBO
From $460 per night (USD)
VRBO
Beautiful Chesapeake Bay Views -pet friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Maryland’s Chesapeake bay is an ever changing panorama of spectacular sunsets, teeming wildlife, graceful sailboats, and ...
From $460 per night (USD)
VRBO
From $607 per night (USD)
VRBO
Away at the Bay: New Home on the Chesapeake Bay!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to Away at the Bay! A new build, 4 bedroom house right on the Chesapeake Bay. Very family friendly, and in walki ...
From $607 per night (USD)
VRBO
From $550 per night (USD)
VRBO
The Lazy River House
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Welcome to this freshly renovated, waterfront home on the Chester River. Gorgeous sunsets, picturesque views of the Rive ...
From $550 per night (USD)
VRBO
From $425 per night (USD)
VRBO
Wye River Cape
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
At "Our Cove on the Wye" this is truly Chesapeake Country and your family memories can be made here. Canoe, kayak or ...
From $425 per night (USD)
VRBO
From $1500 per night (USD)
VRBO
Blake House Historic Estate with Private Inn
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Summary: Blake House represents one of the oldest colonial homes in Maryland, built by British settler, Charles Blake, o ...
From $1500 per night (USD)
VRBO
From $750 per night (USD)
VRBO
Great waterfront house in Grasonville
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Modern Contemporary waterfront house with grand kitchen open floor plan 3 levels overlooking Bay on Eastern shore just m ...
From $750 per night (USD)
VRBO
From $202 per night (USD)
VRBO
Owl Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You won’t forget your time in this romantic, memorable treehouse. A renovated 19th century carriage house, Owl Cottage ...
From $202 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Country Estate in Historic District
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath. Our house ...
From $264 per night (USD)
Expedia
From $98 per night (USD)
VRBO
First Floor Studio Apartment in Historic Chestertown
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everyt ...
From $98 per night (USD)
VRBO
From $329 per night (USD)
VRBO
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Chester River Dreams, offers spectacular views of the Chester River from the Family room, Kitchen, & Dining room, Deck, ...
From $329 per night (USD)
VRBO
From $275 per night (USD)
VRBO
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Beautiful1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic C ...
From $275 per night (USD)
VRBO
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Expedia
Historic downtown Chestertown Home. #1 Location.
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Your family and guests will experience the best of Chestertown in this family friendly and historic home. 2 Blocks from ...
Click For Pricing
Expedia
From $350 per night (USD)
VRBO
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The privacy of a waterfront home welcomes you to pause and enjoy the beauty of the Chester River. Water views from every ...
From $350 per night (USD)
VRBO
From $235 per night (USD)
VRBO
Chestertown's Pet-Friendly Little Red Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our darling, historic cottage, recently featured on Chestertown's Historic House Tour, is comfortable, pet-friendly and ...
From $235 per night (USD)
VRBO
From $1194 per night (USD)
VRBO
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Bedrooms:
7
Bathrooms:
6
Sleeps:
14
Welcome to Riverfront Retreat, a beautiful and spacious home where your family will be able to relax and enjoy the best ...
From $1194 per night (USD)
VRBO
From $710 per night (USD)
VRBO
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Eagle Point Farm located on Maryland's beautiful Eastern Shore, a 90 minute drive from Washington DC, Philade ...
From $710 per night (USD)
VRBO
From $175 per night (USD)
VRBO
Carriage House Hideaway in Middle of Chestertown
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens ...
From $175 per night (USD)
VRBO
From $68 per night (USD)
Expedia
Guest Suite for up to 2 in a Victorian on the Chester River
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Our lovingly-restored Millington Manor is the original home of the local doctor, built in 1868. Our small town has a liq ...
From $68 per night (USD)
Expedia
From $286 per night (USD)
VRBO
Newly restored apartment in the heart of Chestertown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of al ...
From $286 per night (USD)
VRBO
From $143 per night (USD)
VRBO
2 Beds, 2.5 Baths, Perfect Downtown Location
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Quaint and charming, our home away from home in historic Chestertown features 2 bedrooms and 2.5 bathrooms and can accom ...
From $143 per night (USD)
VRBO
From $564 per night (USD)
VRBO
Short Drive to Downtown Easton and St. Michaels | Pool | Newly Renovated | Priva
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Eastern Shore Vacation Rentals presents Sky View. The impressive 4BR, 3.5BA Wye River Sanctuary waterfront estate is cre ...
From $564 per night (USD)
VRBO
From $675 per night (USD)
VRBO
Historic Stepne Manor on Maryland's Eastern Shore
Bedrooms:
4
Bathrooms:
5
Sleeps:
15
Accommodations: Manor House - Five Bedrooms (including one Private Suite), three and one-half Baths, Sitting Room, Den, ...
From $675 per night (USD)
VRBO
From $325 per night (USD)
VRBO
Hidden gem with water and golf course views! Bike ride to downtown!
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Relax by the fire pit and watch the sun set over the pond and golf course! If you like birdwatching, we have amazing gre ...
From $325 per night (USD)
VRBO
From $160 per night (USD)
Expedia
Historic Downtown Garden Oasis with Private Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesth ...
From $160 per night (USD)
Expedia
From $400 per night (USD)
VRBO
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our charming Chestertown Home! This beautiful house offers a comfortable and inviting space for your stay. W ...
From $400 per night (USD)
VRBO
From $217 per night (USD)
Expedia
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape to this stylish, private, waterfront home. Fish or kayak off a private dock on the Chester River and enjoy the vi ...
From $217 per night (USD)
Expedia
$Loft at Fountain Park - Prime Downtown Location\n$
Click For Pricing
VRBO
Loft at Fountain Park - Prime Downtown Location\n
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Perhaps the best apartment in Chestertown. This unique residence blends old-world charm with contemporary luxury and boa ...
Click For Pricing
VRBO
From $643 per night (USD)
VRBO
Victorian Hideaway: Beautiful Exterior, Modern interior
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet ...
From $643 per night (USD)
VRBO
From $775 per night (USD)
VRBO
Breathtaking waterfront home on the Chester River
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Private, one-of-a-kind waterfront home on the Chester River minutes from historic Chestertown. Drive through a gated ent ...
From $775 per night (USD)
VRBO

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Queen Anne's Area Rentals

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Results: 135 Rentals