Holiday rentals in Henderson

Totally Renovated historic house near town center

19th century home. 55” TV in family room, 2 more. 1st floor primary with full bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, 3 block walk from Wash College and the C'town 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 queens Fenced yard, acre of gardens. Fire pit. New Weber grill

Mallard Landing Townhouse

Welcome to Maryland’s Eastern Shore and your own private townhouse in a quiet and peaceful neighborhood. You’ll be conveniently located less than an hour to the beaches, with short travel to Easton, Dover, D.C. and Baltimore. But why bother traveling when your in the beautiful historic town of Denton and all it has to offer with many up and coming stores, restaurants, and many other sights to enjoy including the Choptank River, Martinak State Park, Tuckahoe State Park, and historic downtown.

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

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.

Cozy Apartment B 5GWiFi SmartTV Netflix

Private newly remodeled apartment with Cottage Style decore. Large bathroom with tub. Double fully encased bed with fresh white linens Smart TVs with Hulu, Netflix and local channels. 5G WiFi and smart chargers on night stands Very clean and sanitized bathroom. Full outdoor grill and fire pit Back yard has a small container pond, bird bath and feeder note: The apartments are separated by a locked door on both sides in the front bedroom Each apartment has a separate entrance

Blue Heron Farm Waterfront Chalet

Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of the Chester River. Tucked away on a 126 acre fourth-generation organic farm, the River Chalet is a peaceful and private getaway situated just 15 minutes from historic Chestertown. This recently restored 3-bedroom, 2 bath home features a giant wrap-around deck overlooking the river and floor-to-ceiling windows with serene waterfront views.

Cozy apartment in a quiet Amish country setting

Relax in our fully furnished 1 bedroom (and a spare room with a futon for extra bedding ) 1 bath, living room, and kitchenette apartment, with a private ground level entrance, in a peaceful Amish country setting. The unit is 5 miles away from the Dover city limits. While here, be sure to enjoy shopping at Byler’s Store, a local destination stop featuring a deli, bakery, grocery and gift shop.

The Hepburn-Hot Tub & Fire Pit

The Hepburn is a beautifully renovated and decorated by home by Harlow Grey Homes. This meticulously restored glass cabin is located on over an acre of private grounds on a serene 75 acre lake. Firewood included! The separate seven-person hot tub is OPEN for the season. The private pool + built-in spa is closed and is set to reopen mid May 2025