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

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups. 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 & 14 max guests. Book Today!

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.

The Fitz Inn

Arrive by boat or car to our cozy 1 BD/1BA private 500 sq ft cottage! Enjoy wineries, restaurants, bars & waterfront activities & return to the peaceful Fitz Inn. Sip coffee at sunrise & wine at sunset on Cox Creek (Benton's Pleasure area). Ideal for 2 guests, but can accommodate 4. Listing has AIRBNB exemption from hosting animals, including service & emotional support ones (please see property description for more details). No smoking. Flexible reschedule option with $100 administrative fee.

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

Holiday Escape to the Riverside

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!

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!

Lark's Nest on the Chester River

Escape to this stylish, private, waterfront home. Fish or kayak off a private dock on the Chester River and enjoy the views and dine alfresco on the oversized deck. Centrally located just 20 minutes from all of the events, eateries, shops and galleries in Historic Chestertown. Perfect, family and pet-friendly home for Washington College students, parents and alumni. Book today for your family reunion, wedding parties, or romantic get-away!

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

This unique apartment above the 3 car garage sleeps 4 and is part of the elegant house sitting on 17 private acres in historic Wye Mills with access to a lake. This place is perfect for kayaking, fishing and an overall countryside experience abundant with wildlife. Wye Mills is home to the historic Old Wye Grist Mill which is still in operation as it has been since 1682! Come experience lakeside apartment living.