Holiday houses in Betterton

Ruby's Sea Glass Cottage near Betterton Beach

The whole family will enjoy this cute cottage in the center of Betterton. You can walk to the beach to find sea glass or watch the sunset! There is also a park nearby for kids and adults to enjoy. This house has an adorable kitchen! There are three bedrooms on the second floor, one bathroom on the first floor and three beautiful outdoor porches to unwind. There's parking for 2 vehicles. Kids items upon request. *Furniture and decor may need to be replaced and can change from listing photos.

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested the day of your arrival.

Chestertown - Eastern Shore Getaway

This century-old three-story home is in the beautiful historic district of Chestertown on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue. (NOTE - Airbnb adjusts our rate according to the current demand for rooms)

Cottage By the Chesapeake

This cozy cottage on the Eastern Shore of Maryland sits on a spacious private lot a five minute walk to Betterton Beach! Relax on the screened-in porch or fully-furnished living room after a day at the beach, or cook a homemade dinner in our fully-equipped kitchen. The community of Betterton offers tennis courts, covered outside picnic tables with grills, a brand new playground, and of course...THE BEACH! For a change of pace or a night out, Chestertown, Maryland is only a short drive away.

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.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & 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

Private cozy cottage - center of Chestertown .

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

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!

Baybreeze Cottage

A quiet oasis at the end of a private Lane. A stone's throw from the beach (at end of road and one block down). Huge screened in porch with comfortable seating, wonderful bay breezes, and sunsets over the bay. Inside is cozy and comfortable! Sleeping Arrangements: Bedroom 1: 1 x Queen Bed Bedroom 2: 2x Twin Beds Livingroom: pull out Sofa (Queen Size) Full bathroom with walk in shower Fully stocked kitchen and dining table. Additional dining table on screen porch