Holiday rentals in Stevensville
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Quick stats about holiday rentals in Stevensville
Total holiday rentals
Explore 50 holiday rentals in Stevensville
Nightly prices starting at
Stevensville holiday rentals start at $91 SGD per night before taxes and fees
Verified guest reviews
Over 2,090 verified reviews to help you choose
Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities
Holiday rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 of Stevensville holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Stevensville rentals
4.9 Average rating
Stevensville stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated holiday rentals in Stevensville
Guests agree: these stays are highly rated for location, cleanliness and more.
Private | Near BayBridge | Wedding Venue Proximity
Welcome to your Kent Island getaway! This thoughtfully decorated, private guesthouse is minutes from the Bay Bridge, offering the perfect retreat for families, couples, or friends. Skip the hotel and relax in a fully stocked home with plenty of space, a large backyard for activities, and cozy touches throughout. Whether you're here for a wedding, visiting the Naval Academy or DC, or simply exploring the Eastern Shore, you'll love the comfort, convenience, and local charm this home has to offer.
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.
Cheerful & Spacious Shore Life Beauty!
Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
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.
Beautiful Kent Island Getaway with Pool
PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.
Kent Island Waterfront Home with Amazing Sunsets
Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Relax in this Stylish Coastal-Country Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups! We're 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 or Parties & 14 max guests (8 max adults). Book Today!
Quaint Waterfront- access, Private Shorehouse-unit
Location is everything in this comfy and affordable private unit located on the Chester River and Winchester Creek with water views. Also enjoy the hosts private water front amenities such as fishing at our private pier, boating, kayaking, paddle boarding or simply relax at the waterfront for morning coffee and sunrises or enjoy the fire pit in the evening. The community playground and beach are just steps away. Close proximity to restaurants, shopping, trails, and wedding venues.
Kent Island Waterfront/ Entire Home
Beautiful fully renovated creek-view home in Stevensville, less than 15 minutes from venues, restaurants, bars, and marinas. Features 2 bedrooms: a king master suite and a second room with queen and bunk beds. Enjoy 2 full bathrooms with rain showers, a modern kitchen with all essentials, dining area, 2 living rooms, huge 85” TV, and covered patio overlooking beautiful Thompson Creek. Stores and outlets only minutes away. Perfect for relaxing and beautiful sunsets views!
Cozy home with Screened Porch, Min from Weddings
Tastefully updated 3 bedroom home with everything you need to enjoy Kent Island! Home is conveniently located within minutes from a beach at Terrapin Park, the Cross Island Trail, and Downtown Stevensville. Downtown is home to a few great restaurants and has a new ice cream shop! Other popular destinations, such as Chesapeake Beach Club, Kent Narrows and Annapolis, are within a 10-15 min drive! Come visit us for crab season and enjoy life at the Chesapeake Bay!
Waterfront-View of Bay from your Bed
Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.
Spacious4BR home with waterviews
Welcome to Love Point Lookout! A recently updated 4 bedroom home in a centralized, quiet, location and no shortage of amazing views of the Chesapeake Bay! This home will fulfill the needs of every family member, regardless of age, for your ideal getaway. With a convenient location just miles from the Bay Bridge, Kent Narrows, and Annapolis, the local attractions are just the beginning for this prime location.
Popular amenities for Stevensville holiday rentals
Other great holiday rentals in Stevensville
Waterfront Modern Guest Barn
Chesapeake Houseboat Getaway
Heron Roost
Away at the Bay: New Home on the Chesapeake Bay!
Bayview Bungalow - Water view, EV charging station
Beachside Dream
Island Blue Getaway
*NewHotTub*LuxuryCoastal*CloseToWeddingVenues
When is the best time to visit Stevensville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $279 SGD | $324 SGD | $346 SGD | $354 SGD | $422 SGD | $432 SGD | $422 SGD | $446 SGD | $417 SGD | $422 SGD | $326 SGD | $324 SGD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 14°C | 8°C | 4°C |
Frequently Asked Questions
What are the best places to stay in Stevensville?
Stays around Stevensville's Main Street, residential neighborhoods, and waterfront areas are often recommended for their easy access to local shops and outdoor spaces. Vacation rentals offer a variety of options, including pet and family friendly choices.
What are the best things to do in Stevensville with kids?
Kids often enjoy exploring waterfront parks, visiting playgrounds, and participating in seasonal community events around Stevensville. Kayak rentals, nature trails, and local ice cream shops provide engaging options for families.
What are some of the best things to do in Stevensville?
Explore historic Main Street, enjoy local art galleries, and stroll waterfront parks around Stevensville. Seasonal farmers markets and visits to kayak-friendly marinas are frequently suggested for guests seeking fresh flavors and outdoor activity.
How is the weather in Stevensville?
Stevensville has cool winters around 25–47°F (-4–9°C), and warm, humid summers near 68–89°F (20–32°C). Rain is spread throughout the year; pack layers and a waterproof jacket for comfort.
When is the best time to visit Stevensville?
Late spring through early fall is often recommended for visiting Stevensville, with mild temperatures from 53–89°F (12–32°C) and more outdoor activities. This season also sees frequent festivals and appealing waterfront events.
What are the best places to visit in Stevensville?
Explore historic Main Street with its preserved architecture, visit waterfront parks, or wander local art galleries and markets around Stevensville. Kayak marinas are often suggested for those interested in water activities.
What are some hiking trails in Stevensville?
Stevensville has several nature trails and waterfront paths suitable for hiking and leisurely walks. Parks around the area often have shaded routes and birdwatching spots.
What are some family activities we can do in Stevensville?
Families can explore waterfront parks, rent kayaks, attend seasonal festivals, or enjoy ice cream shops around Stevensville. Nature trails and community events create opportunities for shared experiences.
What are some of the best day trip ideas from Stevensville?
Day trips from Stevensville often include exploring neighboring historic towns, visiting Chesapeake Bay beaches, or touring state parks and wineries around the region. Outdoor activities and cultural sites are frequently suggested.
Are there any pet friendly accommodations available in Stevensville?
Many accommodations in Stevensville are pet friendly, especially vacation rentals near the waterfront and residential neighborhoods. Parks and walking paths make it easy to spend time outdoors with your pet.
What are some local tips for visiting Stevensville?
Locals often recommend exploring Main Street early for quiet shops, packing comfortable shoes for waterfront walks, and sampling seasonal seafood dishes. Early spring and fall bring smaller crowds and distinct regional flavors.
What is Stevensville known for?
Stevensville is known for its Chesapeake Bay waterfront, historic Main Street, and local seafood traditions. The area also has a strong boating culture and preserved Victorian-era architecture.
What are the best hidden gems to explore in Stevensville?
Discover local art studios, tucked-away coffee shops, and small historical museums around Stevensville. Waterfront walking paths and lesser-known marinas offer quiet spots to enjoy the bay.
What are the best foods to try in Stevensville?
Stevensville has fresh Chesapeake Bay seafood such as Maryland blue crabs and oysters, along with seasonal produce and locally made desserts. Steamed crabs and ice cream from local shops are frequently suggested by residents.
What should I bring for a trip to Stevensville?
Bring comfortable walking shoes, a waterproof jacket, and layers for changing temperatures in Stevensville. If you plan to explore waterfronts or parks, consider a hat, sunscreen, and reusable water bottle.
What is the nightlife in Stevensville like?
Nightlife in Stevensville features laid-back bars, waterfront restaurants, and occasional live music venues around Main Street. The scene is often relaxed, with a focus on local flavors and community gatherings.
What are the most popular events or festivals in Stevensville?
Stevensville has events like Kent Island Day in late spring, which highlights local heritage and arts, as well as a community farmers market featuring regional produce and crafts. Smaller waterfront gatherings sometimes celebrate the area's music and seafood traditions.
Are there family friendly vacation rentals in Stevensville?
Stevensville has many family friendly vacation rentals, especially in residential and waterfront neighborhoods. Options often include backyard space, proximity to playgrounds, and flexible layouts for groups.
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- Rentals with a patio Stevensville
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- Rentals with a firepit Stevensville
- Family-friendly rentals Stevensville
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- Georgetown University
- National Mall
- M&T Bank Stadium
- The White House
- Nationals Park
- Walter E Washington Convention Center
- District Wharf
- National Museum of Natural History
- Baltimore Convention Center
- Oriole Park at Camden Yards
- Federal Hill Park
- FedExField
- Johns Hopkins University
- Sandy Point State Park
- Arlington National Cemetery
- National Museum of African American History and Culture
- Capital One Arena
- The Anthem
- Washington Monument
- Georgetown Waterfront Park
- Betterton Beach
- National Harbor
- CFG Bank Arena
- Howard University