Holiday rentals with lake access in Queen Anne's County

Waterfront Paradise w/ Pier - kayak to Chestertown

Escape to our private paradise where you can enjoy breathtaking sunsets from our pier, catch your own fish/crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars, try our outdoor sauna w/panoramic view. It's a destination you can enjoy all year. Our home is located a short bike ride to Historic Chestertown, or you can take one of our kayaks in while you enjoy the Chester River. Bedroom 1: king bed+daybed w/trundle Bedroom 2: Queen Bedroom 3: Queen & bunkbed

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.

Waterfront Getaway

Unwind at this serene and secluded getaway—perfect for couples, small groups, families or anyone looking to relax by the water. This charming one-bedroom guest house offers comfort and style with a plush king-size bed, a fully equipped kitchen with a gas stove, and a spacious living area with a queen-size pullout sofa. Step outside to your private, oversized balcony overlooking the river—an ideal spot for morning coffee, al fresco dining, or winding down with sunset views and a glass of wine.

Crab Alley | Waterfront Home + Hot Tub + Game Room

BNB Breeze Presents: Crab Alley Welcome to Crab Alley, a stunning Bayfront home nestled in the serene surroundings of Chester, Maryland. This beautiful property offers a perfect blend of relaxation and adventure, making it an ideal getaway for families or groups of friends. With its prime waterfront location, guests can enjoy breathtaking views and easy access to water activities right from the comfort of their home. - HOT TUB! - Boat Dock - Deck w/ Bay Views - Game Room - Outdoor Dining table

Pier Pleasure Retreat- Waterfront & Private Pier

Pier Pleasure Retreat is a newly renovated 4-BR, 4-BA waterfront home offering comfort, style, and stunning views of the Cox Creek. Enjoy a gourmet kitchen with a 10-foot island, spacious living areas, and breathtaking sunset views. The private dock is perfect for kayaking, fishing, and crabbing. Relax in the screened-in porch or explore nearby parks and trails. Just 3 miles from the Bay Bridge and close to top dining spots. Book your stay today and experience the ultimate waterfront getaway!

Waterfront escape & walk to historic Chestertown

Relax with the whole family or big group at our peaceful river home. Huge waterfront property. Bedroom, dining and living room river views. River and tidal beach access. Kayak, SUP or canoe. Enjoy backyard games, outdoor dining, hammock or fire pit. Massive waterfront screened-in porch with 2 dining and 2 seating areas. 10 min walk to adorable historic downtown. Festivals, art galleries, bakeries, ice cream, shops, spa & playground. This is our happy place - we hope it becomes yours!

❤️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!

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

Waterfront Modern Guest Barn

Find peace and reconnect with nature at this award winning guest barn. With its simple geometry and bucolic setting overlooking a quiet river of the Eastern Shore, this gem at the edge of a farm field could easily be mistaken for a working barn. But when you slide open the pair of two-story barn doors, you find a beautiful modern guesthouse full of light from the wall of windows facing the river. The setting is incredibly peaceful, and is a wonderful romantic escape or family getaway.

Kent Island Waterfront Home

Enjoy a delightful stay at our waterfront 2 bedroom house for your Kent Island trip. The unit is equipped with a full kitchen including cookware and essentials for all your cooking needs, microwave, Wifi, TV, security cameras. Blankets, pillows, linens and bath towels. The house is a Self-Check-in, perfectly situated near all the local Kent Island Restaurants, Shops, Wedding Venues, Public beach access, wineries and so many more attractions to enjoy. We look forward to hosting you!

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba

Come enjoy the coastal lifestyle of the Chesapeake Bay with friends & family!  **Located in the Prospect Bay Country Club just 15 minutes east of the Bay Bridge.  Relax every evening in the back yard. The setting is incredibly peaceful and a wonderful romantic escape for a family getaway. Find peace and reconnect with nature at this amazing short term rental with 45 feet of undeveloped creek view.    **This spacious home can sleep a MAX of 6 guests. 3br and 3.5 baths!**

Annapolis USNA Waterfront Cottage w/Pier & Firepit

Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier/dock! Gorgeous sunrises! Experience fresh Maryland Crabs & fish caught from your private pier & enjoy the peace, serenity, bay breezes & waterfront green space! Connect to nature and explore Meredith Creek on the Chesapeake Bay by kayak or boat! Super CLEAN & new with water views from dining, living room, kitchen and bedroom! 1.5 miles to the Beach!