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House vacation rentals in Kent Island

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Top-rated house rentals in Kent Island

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Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

"Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take a kayak out after breakfast to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acre in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home (w. 1GB hi-speed internet).

Home in Mechanicsville

4.92 out of 5 average rating, 12 reviews

Modern luxury waterfront - Fall retreat

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

Home in Deale

4.96 out of 5 average rating, 25 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Home in St Michaels

4.85 out of 5 average rating, 118 reviews

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Home in Rock Hall

5 out of 5 average rating, 81 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

Home in Baltimore

4.97 out of 5 average rating, 144 reviews

Full house in “coolest neighborhood in America”

Small but cozy single family in Northern Baltimore, located in the very sought after Hampden neighborhood. 5 minute walk to “the Avenue” and 34th Street lights at Xmas. Directly across the street is a Walgreen’s, MOM’s Organic Market, gym, restaurants, UPS Store, etc. A private driveway, manicured back yard w/ hardscape, fire pit and tons of indoor amenities offer a convenient and relaxing stay in this quaint Baltimore hood. Cleaned by COVID-trained professionals after each reservation.

Home in Edgewater

4.9 out of 5 average rating, 20 reviews

South River Beach Front House

New 2024 Renovated Stunning WATERFRONT South River Beach home!! BEST WATERFRONT LOCATION!!! with heated POOL on the river side & deck 10' from waters edge. Beach, 125' private pier for crabbing & fishing. Comm w/ beach, pier, tennis & basketball courts. (1) Main LVL: entry foyer, sunroom, stunning kitchen, dinning area, & living room w/FP. Main level owners suite w/full bath, & 1/2 bath. (2) Upper level: 2 bedrooms w/ full bath & upper LVL sitting area & sun deck w/expansive river views

Home in Cambridge

4.98 out of 5 average rating, 121 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Come relax at our casual, pristine waterfront home. We offer 4 bedrooms w/7 beds for 10 guests. We are nestled in a small neighborhood on the beautiful Choptank River. We provide bikes, kayaks, paddleboards & yard games. Just want to relax? Enjoy hanging in the hammock or kick back on the waterfront w/a private pier. Try fishing off the pier or simply chill on the back deck or patio. At night hang out by the firepit. Explore downtown Cambridge - it's a short walk/bike ride to town.

Home in Cambridge

4.94 out of 5 average rating, 119 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Home in Annapolis

5 out of 5 average rating, 119 reviews

Luxury Waterfront Annapolis/ Private Beach & Dock

Stunning Contemporary Home recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.

Home in Annapolis

4.93 out of 5 average rating, 117 reviews

Eastport Haven House

Welcome to our custom Craftsman in the exclusive Maritime Eastport section of Annapolis. Surrounded by the city's best restaurants ( Ruth's Chris, ChartHouse , Vin 909 and many many others )and home to some very famous neighbors it's one one of the most desirable locations in town. A short stroll across a quaint drawbridge and your downtown for shopping USNA . Very spacious home with 4 bedrooms 4 baths , parking for 4 cars and a pool table. Truly a million plus dollar property !

Home in Annapolis

4.92 out of 5 average rating, 106 reviews

Historic Downtown House with Off Street Parking

Spacious living with all the modern amenities. Prime location - 1 block from the water, restaurants, and shops. Park your car off street (up to 3 cars) and you won't need it again! Gourmet kitchen fully stocked and ready for entertaining, enjoy the outdoor space. The whole group will enjoy easy access to everything from this centrally located place.

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Popular amenities for Kent Island house rentals

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House rentals with a pool

Home in Edgewater

4.92 out of 5 average rating, 138 reviews

House in Edgewater Maryland

Home in Woolford

5 out of 5 average rating, 114 reviews

Starboard on McKeil Point, w/heated pool & hot tub

Home in Queenstown

4.81 out of 5 average rating, 155 reviews

Bay Breeze Retreat

Home in Cambridge

4.96 out of 5 average rating, 111 reviews

Waterfront, Fabulous Home for Families with Pool!

Home in Severn

4.86 out of 5 average rating, 139 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

Home in Fort Washington

4.94 out of 5 average rating, 128 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

Home in Tracys Landing

4.99 out of 5 average rating, 195 reviews

The Little Gypsy BoHome

Home in Stevensville

5 out of 5 average rating, 124 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Weekly house rentals

Home in Baltimore

4.73 out of 5 average rating, 22 reviews

Townhouse 3 Bedrooms/2 Baths/ Gated Free Parking

Home in Wye Mills

4.91 out of 5 average rating, 11 reviews

⇚Family Getaway⇛| Lakeside + A Nature View |

Home in Washington

4.95 out of 5 average rating, 172 reviews

Beautiful Capitol Hill Row House

Home in Washington

4.92 out of 5 average rating, 50 reviews

Light-Filled Victorian Town-Home

Home in Shady Side

5 out of 5 average rating, 143 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Home in Cambridge

4.95 out of 5 average rating, 223 reviews

Great Historic Cambridge Home With Parking!

Home in College Park

4.82 out of 5 average rating, 169 reviews

Spacious relaxing home by DC, CP, woods & lake

Home in Deale

4.98 out of 5 average rating, 103 reviews

140ft Dock, Pet-Friendly 8 Acre Waterfront Oasis !

Private house rentals

Home in Washington

5 out of 5 average rating, 8 reviews

New Cozy Home In NW DC Sleeps 12

Home in North Beach

5 out of 5 average rating, 14 reviews

Stunning North Beach Getaway w/ Inground Pool

Home in Rock Hall

4.94 out of 5 average rating, 35 reviews

Rockfish Keeper

Home in Edgewater

4.98 out of 5 average rating, 52 reviews

Entire Beach House with Pool and Hot Tub

Home in Arnold

4.81 out of 5 average rating, 26 reviews

Entire Private 2 bedrooms house, nice neighborhood

Home in Centreville

4.63 out of 5 average rating, 92 reviews

Peaceful Acres Guest House (A Nature's Getaway)

Home in Pasadena

5 out of 5 average rating, 38 reviews

Waterfront CHeerful 2 with Private home

Home in Washington

4.98 out of 5 average rating, 106 reviews

Charming Bloomingdale Row Home with Deck & Parking

Destinations to explore