
House vacation rentals in Centreville
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Top-rated house rentals in Centreville
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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.
4.95 out of 5 average rating, 310 reviews
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.
4.91 out of 5 average rating, 116 reviews
River House on the Choptank
Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.
4.93 out of 5 average rating, 126 reviews
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.
4.97 out of 5 average rating, 131 reviews
Cozy 3-bedroom home w/ Hot tub & firepit
This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.
4.98 out of 5 average rating, 193 reviews
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.
4.99 out of 5 average rating, 149 reviews
The Patriot House-Chestertown, MD
Welcome to the Patriot House in Chestertown, Maryland. We recently renovated this beautiful home with a "Mad Men" Mid-Century modern vibe throughout. This is Two Units that combine together with connecting door for a total of 6 bedrooms and 3 remodeled bathrooms. You are renting entire first and second floors. Two kitchen and two living rooms. Wide front porch is perfect for cocktails or morning coffee. 2 blocks to Washington College and Downtown. We do not rent to undergrad students.
4.96 out of 5 average rating, 135 reviews
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views
4.96 out of 5 average rating, 117 reviews
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!
4.93 out of 5 average rating, 362 reviews
Cozy 2 bedroom home on wooded private lane
Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.
4.97 out of 5 average rating, 144 reviews
Cozy 1920's Bungalow Near Water/Local Attractions
Updated 1920's bungalow near all Rock Hall has to offer. Blocks away from the Bay, marinas and center of town. Coffee shop, grocery and other shops 2 blocks away. Walk to several restaurants. Cozy and very comfortable. Quiet street, and peaceful at night. This house is an ideal Rock Hall location. This home is well stocked, so most condiments, coffee, tea, sodas and water are included. There are also many toiletry and first aid products. No need to bring soap or shampoo.
4.99 out of 5 average rating, 130 reviews
River front cottage with private dock & water fun
Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!
4.96 out of 5 average rating, 105 reviewsPopular amenities for Centreville house rentals
House rentals with a pool

Miles Aweigh
4.97 out of 5 average rating, 299 reviews
Chester Riverfront At Kent Narrows
5.0 out of 5 average rating, 326 reviews
Gorgeous, Waterfront Home Is Perfect for Families!
4.96 out of 5 average rating, 140 reviews
Gunpowder Retreat
4.98 out of 5 average rating, 149 reviews
The Little Gypsy BoHome
4.99 out of 5 average rating, 251 reviews
SM's Premier Rental Heated Pool (closes 10/27)
4.97 out of 5 average rating, 116 reviews
Bay Bliss House
5.0 out of 5 average rating, 40 reviews
Waterfront Wellness - *With Pool and Hot Tub!*
4.9 out of 5 average rating, 30 reviewsWeekly house rentals

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water
4.98 out of 5 average rating, 110 reviews
Waterfront Sanctuary only 50 Min. From DC/Balt.
4.97 out of 5 average rating, 110 reviews
Waterfront Cheerful 5 home
4.95 out of 5 average rating, 178 reviews
Waterfront CHeerful 2 with Private home
4.98 out of 5 average rating, 101 reviews
Iconic Chesapeake. Unparalleled Luxury.
5.0 out of 5 average rating, 213 reviews
Family Retreat at Historic Lansdowne Manor
5.0 out of 5 average rating, 62 reviews
Charming Haven on High
4.96 out of 5 average rating, 75 reviews
High Tide & Hound
4.97 out of 5 average rating, 95 reviewsPrivate house rentals

Bay Breeze - 3BR Waterfront Chester River Retreat
5.0 out of 5 average rating, 88 reviews
Magnolia House is for sale! Historic Chestertown
5.0 out of 5 average rating, 61 reviews
Charming Cape By The Bay!
4.95 out of 5 average rating, 91 reviews
Heart of Historic Chestertown - Church Alley
5.0 out of 5 average rating, 16 reviews
Lovely Home in Chestertown With Free EV Charging
5.0 out of 5 average rating, 100 reviews
Water Views in Rock Hall
5.0 out of 5 average rating, 71 reviews
*NewHotTub*LuxuryCoastal*CloseToWeddingVenues
4.97 out of 5 average rating, 74 reviews
Screened Porch | Near Bay Bridge & USNA | Big Yard
4.98 out of 5 average rating, 53 reviewsDestinations to explore
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- Baltimore Museum of Art
- Six Flags America
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- Annapolis City Dock
- Downtown Annapolis Partnership
- University of Maryland





