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Luxury Townhome w/free parking

Welcome to this luxurious, updated and stylish home that is centrally located, yet tucked away in a peaceful area with inside & outside dining. This 2 bed/1.5 bath home is has beautiful lighting, laminated floors, high ceilings, large rooms w/king bed & comfortable sofa for reading or relaxing in the master bedroom. The second room has 2 full beds. The kitchen is updated with all the necessary appliances and utensils that even a chef would enjoy and flows into the classy living/dining area.

Connection Pointe•River views•Quiet•Peaceful

Connection Pointe is a great getaway for your family vacation or to reconnect with friends, you will be sure to enjoy this beautiful property that sits right along the Sassafras River, it is quiet and peaceful with amazing views from the house and the screened in deck. Come enjoy the sounds of nature as you take time to relax and refocus! There is no boat access to the river from the property. There is a fairly steep bank going down to the river, so please be mindful of this with children.

Stunning 2BR Cottage w/River views

Cozy Riverside Cottage in Scenic Hacks Point on the Bohemia 2BR | 1.5BA | Steps from the Water | Family-Friendly Escape the everyday and unwind in this charming riverside cottage with views of the Bohemia River. Whether you're looking for a weekend getaway, a week-long family retreat, or a beautiful place to stay while attending a nearby event or wedding, our 2-bedroom, 1.5-bathroom cottage offers the perfect blend of comfort and charm with direct access to the beautiful Bohemia River.

Quiet Country Relaxing Farm

Forget your worries in this spacious and serene space. This 3 bedroom 2 bath home is set way out in the country surrounded by state hunting lands .With some farm animals on the property now and then .So much wild life. Lots of deer and turkeys to name a few . Would be a perfect place to stay during hunting season with a short walk out the front door you will be deep in the state hunting lands .Also just up the road is Double Tap Tavern cold drinks and amazing food. High speed internet

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 historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Hunter's Lodge

Escape to our charming countryside cottage nestled on a picturesque farm on the Eastern Shore and just a stone’s throw from Delaware. Surrounded by rolling fields, this cozy retreat offers the perfect blend of rustic charm and modern comfort. Enjoy morning coffee on the porch, explore nearby towns and outdoor experiences. With easy access to local attractions, you can experience farm life while being close to charming towns and beautiful landscapes. Your serene getaway awaits!

Long Beach Cottage, Hot Tub, Beachfront

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Delightful 12x16 Glamping Gazebo/Tent

Rustic/Glamping Gazebo/Tent situated privately on our property (backyard) of 1.5 acres in a residential neighborhood. As it says Rustic and “Glamping”..meaning an upgraded camping experience, but by no means can we offer the same comfort temperature wise as an indoor setting. A fun stop for the night, or enjoy a full evening with a movie and firepit. Also, there are plenty of restaurants to choose from in the area, as well several local breweries.

Carriage House Studio -Secluded "Treehouse" Escape

Escape to a hidden sanctuary in Chestertown. Perched on the 2nd floor of a historic building, this private 800 sq ft carriage house feels like a luxury treehouse with canopy views, fully screened from the outside world. Perfect for a romantic getaway or solo retreat, it blends total privacy with town-center access. Enjoy a fireplace, premium linens, off-street parking, and full access to over an acre of breathtaking private gardens.

Bohemia Bungalow

Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Private off street parking for 2 cars.

The Peaceful Getaway (with private pool & hot tub)

Kick back and relax at this charming peaceful getaway, the perfect place to enjoy with friends and family! This beautiful 2 story spacious house is back off a dead end road, but still only minutes from the main highway. It’s very private with a beautiful in ground pool and hot tub behind the house! And also lots of space for outdoor cooking. Please no pets