House holiday rentals in Centreville

Rachel's BnB

A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

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.

Waterfront Chesapeake Bay Sunrises & Fishing Pier!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Quaint in the Heart of Annapolis

Quaint 2 bedroom, 1 bath home located in the heart of historic Annapolis. Completely remodeled with free off-street parking. Located towards the end of a safe, quiet, dead end road, less than 3 miles from downtown Annapolis, the Naval Academy, the Annapolis Mall, St. John’s College, and the Navy-Marine Corps Memorial Stadium. Walk downtown or to the Annapolis Town Center, restaurants, shops, and so much more! -Wi-Fi -2 free parking spaces -Keurig Coffee -TV -Toothbrushes/Paste -Shampoo/Soaps

Hist. home one block from town center /NFL Ticket

19th century home. NFL Sun Ticket! 55” TV in family room, 2 more. 1st floor primary with full bath. Hi speed internet. Pets welcome! In the historic district of Chestertown, 3 block walk from Wash College and the waterfront. 2 primary bedroom suites (one on 2nd floor with king ) 2 bedrooms with queens. 100% cotton, 1000 thread count sheets and luxury mattresses. Loft connected to a 2nd story bedroom with queen bed. Fenced yard, acre of gardens. Fire pit. Weber grill

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.

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.

Beautiful Baycation Stay

This Baycation stay is perfect for friends and family looking for a waterfront stay just 25 minutes from BWI Airport, Downtown Baltimore and Downtown Annapolis. Offering amenities like kayaks, crabbing, paddle boards, firepit, WiFi with all streaming services and toiletries to make sure you have everything in case you forget. There is a home office space set up! Kitchen stocked for home cooking, relaxing, and a guest book for eating out.

Jewell on the Chesapeake

626 Hills Point on Brannocks Bay off of the Chesapeake Bay is one of the most peaceful beautiful places on the Eastern shore. Our recently renovated 3 bedroom single bath home sits on 3 acres of pristine waterfront with a new 80 ft private dock, with 300 ft of Chesapeake shoreline. The perfect place for kayaking, paddle boarding, fishing, crabbing, boating or just relaxing watching the wildlife.

Beautiful, quiet waterfront house. Lots of room!

Quiet retreat with a beautiful waterfront view for the whole family and more. Many fun amenities! Minutes from many great restaurants and a drive-in theater. Thirty minutes to the football or baseball stadiums. Fourty minutes from BWI Airport. Fourteen minutes from White Marsh with shopping and many more restaurants galore.

Duchess of Kent: Walk to downtown & College

Location location location! We absolutely love the proximity of our house to campus, the historic district, and the river. Chestertown is charming and there are fun little shops and restaurants around every corner. Our home is cozy and perfect for entertaining. We hope you enjoy it as much as we do!