Vacation rentals in Stevensville

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Top-rated vacation rentals in Stevensville

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

Guest favourite

Apartment in Stevensville

4.97 out of 5 average rating, 239 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Aug. 16 – 23

$296 CAD per night
Guest favourite

Home in Stevensville

4.94 out of 5 average rating, 185 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!

Feb. 17 – 24

$344 CAD per night
Superhost

Apartment in Grasonville

4.89 out of 5 average rating, 173 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.

May 7 – 14

$248 CAD per night

Popular amenities for Stevensville vacation rentals

Stay near Stevensville's top sights

Terrapin Nature Park34 locals recommend
Chesapeake Bay Beach Club5 locals recommend
Hemingway's Restaurant18 locals recommend
Rams Head Shore House15 locals recommend
Stevensville Crab Shack10 locals recommend
El Jefe Mexican Kitchen & Tequila Bar16 locals recommend

Other great vacation rentals in Stevensville

Guest favourite

Home in Stevensville

5.0 out of 5 average rating, 20 reviews

Away at the Bay: New Home on the Chesapeake Bay!

Mar. 12 – 19

$792 CAD per night
Guest favourite

Home in Stevensville

5.0 out of 5 average rating, 79 reviews

Kent Island Waterfront Home with Amazing Sunsets

Nov. 1 – 8

$738 CAD per night
Superhost

Home in Stevensville

5.0 out of 5 average rating, 3 reviews

Beachside Dream

Sep. 26 – Oct. 3

$670 CAD per night
Guest favourite

Home in Stevensville

4.95 out of 5 average rating, 40 reviews

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

Oct. 5 – 12

$829 CAD per night
Guest favourite

Cottage in Stevensville

4.93 out of 5 average rating, 15 reviews

Cozy, Waterfront Getaway “The Great Nest”

Oct. 9 – 16

$553 CAD per night
Guest favourite

Home in Stevensville

4.98 out of 5 average rating, 61 reviews

Beautiful Kent Island Getaway with Pool

Nov. 12 – 19

$1,112 CAD per night
Guest favourite

Guesthouse in Chester

5.0 out of 5 average rating, 39 reviews

Waterfront Guest Cottage: Sunsets, Pool, Pier

Jan. 12 – 19

$1,011 CAD per night
Guest favourite

Home in Stevensville

5.0 out of 5 average rating, 99 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Aug. 15 – 22

$1,427 CAD per night
Guest favourite

Home in Stevensville

5.0 out of 5 average rating, 15 reviews

Impressive Waterfront Home - Pool, Pier, & Sunsets

Apr. 9 – 16

$1,695 CAD per night
Guest favourite

Home in Stevensville

5.0 out of 5 average rating, 34 reviews

The Pool House in Romancoke On The Bay

Oct. 22 – 29

$1,187 CAD per night
Guest favourite

Guesthouse in Stevensville

5.0 out of 5 average rating, 23 reviews

Chesapeake Cottage

Dec. 8 – 15

$320 CAD per night
Guest favourite

Home in Stevensville

4.97 out of 5 average rating, 95 reviews

The Kent Island House

May 2 – 9

$400 CAD per night

Quick stats about vacation rentals in Stevensville

Total rentals

30 properties

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

1.4K reviews

Destinations to explore