Vacation rentals with a patio in Kent Island

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Top-rated patio rentals in Kent Island

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Guest favorite

Home in Stevensville

4.94 out of 5 average rating, 196 reviews

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

Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/3 acres of outdoor living! Perfect for Families & sleeps 14. We are conveniently located to many areas/cities: Annapolis- 15 miles Baltimore- 40 Wash. DC- 45 Easton- 30 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions, including Chesapeake Beaches. This is a Non-Smoking House. Also No Pets, Parties or Large Groups (14 max.). Book Today!

Jan 26 – Feb 2

G$46,383 GYD per night

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 117 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

Jan 18 – 25

G$87,632 GYD per night

Guest favorite

Home in Chester

5.0 out of 5 average rating, 12 reviews

*Waterfront Sunset Bayview* sleeps 6

Welcome to our beautiful, completely renovated waterfront home in the heart of Kent Island! Our home has magnificent direct sunset views, that force you to stop and take it in! Our open-concept home is tastefully decorated with a blend of modern amenities and cozy charm, complete with large windows that allow natural light to fill the space along with stunning views of the Bay. Escape the hustle of everyday life and immerse yourself in the serene beauty from the comfort of your private retreat.

Sep 5 – 12

G$81,962 GYD per night

Guest favorite

Houseboat in Kent Narrows

4.97 out of 5 average rating, 71 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

Feb 19 – 26

G$32,923 GYD per night

Guest favorite

Guesthouse in Wye Mills

4.94 out of 5 average rating, 17 reviews

Adorable Lake Front 1BR Cottage-fully furnished!

This charming 1BR/ 1Bath cottage is located next to my primary residence. The cottage has its own private deck overlooking the Wye Mills Community Lake. The yard is spacious and pets are welcome. The yard is not closed in but safe for dogs who do not roam far. There is 1 queen size bed and queen pull out couch in the living room. Kitchen is equipped with basic appliances/ cooking and serving utensils and a full size washer and dryer. The bathroom has a stand up shower and basic necessities.

Oct 7 – 14

G$18,145 GYD per night

Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 10 reviews

Beachside Dream

Kick back and relax in this calm, stylish space, 4 bedroom 3 full bathroom, Sandy Beach front, stunning sunset. An hour from DMV. Wall of windows in the Living Room overlooks the evening sunsets on the Bay. Sun room with the stunning views of bay. Spacious rooms for up to 12 guests($50 charge per guest after 8 guest) 10 minute drive from popular wedding venues, Chesapeake Bay Beach Club and Silver Swan. Hotel quality linens and towels are provided, unlimited High Speed WIFI , 3- Smart TV

Jan 3 – 10

G$90,488 GYD per night

Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 103 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!

Dec 14 – 21

G$28,287 GYD per night

Guest favorite

Home in Stevensville

4.96 out of 5 average rating, 48 reviews

25-50% Off~Private Beach~Hot Tub~Fire Table~

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

Sep 13 – 20

G$114,717 GYD per night

Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 40 reviews

Modern Island Escape by the Bay

Welcome to Island Time! We think you are going to love it here! This home has just gone through a renovation completed in 2023. We went with the Island theme starting with our massive Kitchen Island, which serves as the hub of the house. Right off the kitchen is our back deck that spans the length of the house and over looks the paver patio, fire pit below. We are centrally located to all the wedding venues, restaurants, and Bay Bridge access to Annapolis, DC, and beyond.

Oct 9 – 16

G$49,901 GYD per night

Guest favorite

Cottage in Stevensville

4.93 out of 5 average rating, 15 reviews

Cozy, Waterfront Getaway “The Great Nest”

Looking for a relaxing, 'away from it all' getaway with close proximity to Annapolis, DC & Baltimore (about 5 minutes from Bay Bridge). This special property sits ON the water known as Warehouse Creek. Enjoy morning coffee on the patio overlooking the water or by the fountain pond and wine in the evenings under the stars. Nature lovers paradise. 3 kayaks, 1 canoe, crab box traps, and fishing rods available. Try out your hand with crabbing off the dock!

May 17 – 24

G$78,000 GYD per night

Guest favorite

Guest suite in Arnold

4.94 out of 5 average rating, 118 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Yes, the hot tub IS open! 24/7/365 :-) Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Jul 15 – 22

G$36,623 GYD per night

Guest favorite

Guest suite in Annapolis

4.97 out of 5 average rating, 117 reviews

Great reviews! Pool, DT, stadium, goats, and more!

Welcome to our private guest suite in walking distance to the Navy-Marine Corps Memorial Stadium. Enjoy the indoor pool (June-September), furnished deck and patio, wood-burning stove and more. Have access to community piers, waterfront parks, and soft launches on the Severn River. The sights and sounds of downtown Annapolis are minutes away. All while being centrally located between Washington DC, Baltimore, and the Eastern Shore.

Jan 8 – 15

G$34,680 GYD per night