Vacation rentals in Stevensville

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Top-rated vacation rentals in Stevensville

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Guest favorite

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.

Oct 14 – 21

$169 per night

Guest favorite

Home in Stevensville

4.94 out of 5 average rating, 191 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!

Dec 14 – 21

$242 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.

Oct 31 – Nov 7

$146 per night

Guest favorite

Guest suite in Arnold

4.96 out of 5 average rating, 562 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

$98 per night

Guest favorite

Houseboat in Grasonville

4.99 out of 5 average rating, 115 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!

Feb 11 – 18

$150 per night

Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 100 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine. Travel just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered patio on main level and 12' x 52' three season room on the upper level.

Mar 10 – 17

$833 per night

Guest favorite

Home in Grasonville

4.94 out of 5 average rating, 224 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

Sep 14 – 21

$481 per night

Guest favorite

Cottage in Annapolis

4.94 out of 5 average rating, 312 reviews

Wright’s Cottage, Pets Welcome!

We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!

Aug 22 – 29

$131 per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 205 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.

Oct 26 – Nov 2

$85 per night

Guest favorite

Guest suite in Stevensville

4.97 out of 5 average rating, 145 reviews

Kent Island Haven - A Waterfront Getaway

Located across the bay from Annapolis, Kent Island Haven is a convenient and beautiful alternative to a hotel. Near shopping, nature areas, and walking trails; as well as the fine restaurants and water-oriented features of the Eastern Shore. Convenient to Baltimore, DC, Easton and St. Michaels. This 600 square foot 1 BR/1 BA in-law apartment has a private entrance and full kitchen. Watch the ships and ospreys from the living room. Enjoy the waterside hammock, pier, patio, and garden.

Mar 27 – Apr 3

$164 per night

Guest favorite

Home in Annapolis

4.99 out of 5 average rating, 197 reviews

Cape St Claire waterfront getaway

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

Nov 13 – 20

$126 per night

Guest favorite

Cottage in Stevensville

4.94 out of 5 average rating, 130 reviews

Cottage on the Bay - Kent Island

Chesapeake Bay Waterfront home on Kent Island! Enjoy year round big sky and water views from the comfort of the screened porch & family room. Fish & crab from the pier (shared with our aunt & uncle next door) or take a dip in the bay. Open concept living and rear bedroom/rec room are perfect for relaxing and having fun with family & friends. Close to popular wedding venues, local marinas & charter fishing boats, restaurants, Tiki bars, beaches, golfing, parks, &bike trails

Aug 20 – 27

$536 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Stevensville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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 favorite

Home in Stevensville

4.85 out of 5 average rating, 48 reviews

Cheerful & Spacious Shore Life Beauty!

Feb 20 – 27

$207 per night

Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 23 reviews

Chesapeake Cottage

Jul 10 – 17

$184 per night

Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 39 reviews

Modern Island Escape by the Bay

Dec 27 – Jan 3

$208 per night

Guest favorite

Home in Chester

5.0 out of 5 average rating, 10 reviews

*Waterfront Sunset Bayview* sleeps 6

Dec 16 – 23

$341 per night

Guest favorite

Houseboat in Stevensville

4.96 out of 5 average rating, 26 reviews

Chesapeake Houseboat Getaway

Sep 23 – 30

$298 per night

Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 7 reviews

Gable’s Landing on the River.

Oct 31 – Nov 7

$404 per night

Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 79 reviews

Kent Island Waterfront Home with Amazing Sunsets

Nov 10 – 17

$440 per night

Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 7 reviews

Beachside Dream

Dec 29 – Jan 5

$375 per night

Show all

Quick stats about vacation rentals in Stevensville

Total rentals	40 properties
Wifi availability	40 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	30 properties are a good fit for families
Total number of reviews	1.5K reviews

Frequently Asked Questions

Are there family-friendly vacation rentals in Stevensville?
Stevensville has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Stevensville have wifi?
Absolutely! We offer over 30 house rentals with wifi in Stevensville. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Stevensville have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Stevensville. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Stevensville have free parking?
Absolutely! We offer over 20 house rentals with free parking in Stevensville. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Stevensville?
Yes! Work meets play with ease at over 20 vacation rentals in Stevensville featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Stevensville have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Stevensville. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Stevensville?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Stevensville?
Four-legged friends are welcome in Stevensville. Choose from more than 10 vacation rentals for guests traveling with pets.

Vacation rentals in Stevensville

Top-rated vacation rentals in Stevensville

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Stevensville vacation rentals

Stay near Stevensville's top sights

Other great vacation rentals in Stevensville

Home in Stevensville

Guesthouse in Stevensville

Home in Stevensville

Home in Chester

Houseboat in Stevensville

Home in Stevensville

Home in Stevensville

Home in Stevensville

Quick stats about vacation rentals in Stevensville

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there family-friendly vacation rentals in Stevensville?

Do house rentals in Stevensville have wifi?

Do house rentals in Stevensville have air conditioning?

Do house rentals in Stevensville have free parking?

Are there vacation rentals with a dedicated workspace in Stevensville?

Do house rentals in Stevensville have a kitchen?

What are the most popular amenities for House Rentals in Stevensville?

Are there pet-friendly vacation rentals in Stevensville?

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