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Queenstown vacation rentals

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Top-rated vacation rentals in Queenstown

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Apartment in Grasonville

4.89 out of 5 average rating, 174 reviews

Halcyon house. Lovely views on MD eastern shore.

This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to some restaurants.

Jan 29 – Feb 5

€ 173 per night

Houseboat in Grasonville

4.99 out of 5 average rating, 116 reviews

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

Dec 30 – Jan 6

€ 211 per night

Guest suite in Arnold

4.96 out of 5 average rating, 565 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Jul 1 – 8

€ 119 per night

Home in Grasonville

4.94 out of 5 average rating, 225 reviews

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

Nov 3 – 10

€ 505 per night

Home in Queenstown

4.81 out of 5 average rating, 143 reviews

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

Nov 12 – 19

€ 936 per night

Apartment in Greenwood

4.97 out of 5 average rating, 479 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Dec 13 – 20

€ 78 per night

Guesthouse in Annapolis

4.9 out of 5 average rating, 206 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Dec 10 – 17

€ 114 per night

Casa particular in Chestertown

4.93 out of 5 average rating, 102 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Jan 12 – 19

€ 139 per night

Apartment in Frederica

4.97 out of 5 average rating, 258 reviews

Smokefree Lakeside Relaxation

Quiet smoke free lakefront Carriage House studio over garage with separate entrance. Mini Fridge, microwave, dishes. Use of fire pits, canoe, SUP, dock. Lake is fishable and swimmable. Flatscreen HDTV with Premium Channels. WiFi to use with your own device or use my laptop in unit. 45 min from beach. 20 minutes to Dover. 4 parks with walking paths within 10 miles. Close to Dover Air Force Base but not in flight path. Well behaved social pets with responsible owners are welcome!

Apr 4 – 11

€ 91 per night

Guest suite in Chestertown

4.99 out of 5 average rating, 191 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Sep 13 – 20

€ 147 per night

Guesthouse in Easton

4.99 out of 5 average rating, 545 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

Mar 21 – 26

€ 150 per night

Apartment in Chester

4.97 out of 5 average rating, 234 reviews

Cozy Waterfront Apartment Chester, MD

*We live on the property* Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. Plus an easy to assemble blow up air mattress to sleep an additional two. WiFi included. Private porch to sit & enjoy beautiful water views!

Sep 15 – 22

€ 171 per night

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Popular amenities for Queenstown vacation rentals

Laptop-friendly workspace

Air conditioning

Other great vacation rentals in Queenstown

Home in Annapolis

4.99 out of 5 average rating, 198 reviews

Cape St Claire waterfront getaway

Nov 13 – 20

€ 153 per night

Tiny home in Cambridge

4.99 out of 5 average rating, 156 reviews

Blackwater Refuge House on The Farm, water access

Aug 23 – 30

€ 112 per night

Cottage in Saint Michaels

4.99 out of 5 average rating, 136 reviews

La Casita on Harris Creek, St. Michaels

Jun 2 – 9

€ 545 per night

Apartment in Pasadena

4.99 out of 5 average rating, 547 reviews

Sea Dreamer aka Phenomenal Hospitality

Feb 21 – 28

€ 100 per night

Apartment in Crownsville

4.98 out of 5 average rating, 164 reviews

“River Sweet" Private Apartment

Aug 13 – 20

€ 133 per night

Guesthouse in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Jul 18 – 25

€ 135 per night

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Dec 17 – 24

€ 128 per night

Farm stay in Madison

4.98 out of 5 average rating, 163 reviews

Madison Nature Getaway

Jul 10 – 17

€ 127 per night

Other great vacation rentals in Queenstown

Guesthouse in Stevensville

5.0 out of 5 average rating, 207 reviews

Waterfront Getaway - View of bay from your bed

Sep 25 – Oct 2

€ 289 per night

Guest suite in Chestertown

4.99 out of 5 average rating, 131 reviews

Chestertown - Eastern Shore Getaway

Sep 30 – Oct 7

€ 138 per night

Apartment in Essex

4.97 out of 5 average rating, 223 reviews

A place unique on sue creek

Aug 3 – 10

€ 105 per night

Cottage in Annapolis

4.94 out of 5 average rating, 314 reviews

Wright’s Cottage, Pets Welcome!

Oct 9 – 16

€ 183 per night

Guesthouse in Wye Mills

4.94 out of 5 average rating, 16 reviews

Adorable Lake Front 1BR Cottage-fully furnished!

Oct 15 – 22

€ 101 per night

Guesthouse in Queenstown

4.9 out of 5 average rating, 20 reviews

Waterfront Getaway

Jan 21 – 28

€ 191 per night

Barn in Queenstown

5.0 out of 5 average rating, 41 reviews

Waterfront Modern Guest Barn

Oct 21 – 28

€ 645 per night

Guesthouse in Centreville

4.84 out of 5 average rating, 74 reviews

Centreville Cottage

Oct 6 – 13

€ 162 per night

Destinations to explore