Holiday houses in Henderson

4.92 out of 5 average rating, 210 reviews

Guest suite in Lincoln

Nicencozy, near DE Turf, Bayhealth, beaches, AFB

Stay in peace at this smoke-free, quiet abode. Within 10 mins of Milford (Bayhealth Sussex, Walmart, shopping, pharmacies, restaurants, etc.). 15 mins: DE Turf, Milton, breweries. 20-30 mins: Bowers Bch, Pickering Bch, Sports at the Bch, Dover & Georgetown, theaters & casinos. 30-45 mins: other beaches and outlets. Please review Guide Book and House Manual after booking, and call us after a last minute booking, so we can tell you how to get in. Snacks, water, etc. provided while supplies last.

Guest suite in Chestertown

4.99 out of 5 average rating, 225 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

4.93 out of 5 average rating, 129 reviews

Home in Denton

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.

4.97 out of 5 average rating, 583 reviews

Apartment in Greenwood

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)

4.97 out of 5 average rating, 235 reviews

Apartment in Chestertown

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.

4.96 out of 5 average rating, 305 reviews

Apartment in Frederica

Smokefree Lakeside Relaxation

Quiet smoke free lakefront Carriage House studio over garage with separate entrance. Mini Fridge, microwave, dishes. Use of fire pits, canoe, SUP, dock. Lake is fishable and swimmable. Flatscreen HDTV with Premium Channels. WiFi to use with your own device or use my laptop in unit. 45 min from beach. 20 minutes to Dover. 4 parks with walking paths within 10 miles. Close to Dover Air Force Base but not in flight path. Well behaved social pets with responsible owners are welcome!

5 out of 5 average rating, 110 reviews

Apartment in Chestertown

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!

4.97 out of 5 average rating, 33 reviews

Barn in Dover

The Barn

Welcome to the Barn. It can host up to 4 guests. The bedroom is private with a queen size bed, a closet and a tv. In the living room there is a sleeper sofa that converts to a queen size bed. The living room tv can be enjoyed throughout as the space is open. Step out onto the porch and enjoy the sunrise in the morning and the horses throughout the day. The barn is only 35 miles to the beaches and only 12 miles to DE Turf. Within 1 mile you will find stores, dog parks and playgrounds.

4.99 out of 5 average rating, 137 reviews

Apartment in Frederica

Entire 1-Bedroom apt. - Private entrance in home

This centrally located, clean, 2nd floor apartment in our home is the perfect place to rest. Features very large bedroom with a new king bed with a hybrid mattress, and spacious living room with a queen size pull out couch. Well equipped kitchen with toaster oven, electric skillet, countertop burner, microwave, and coffee makers. Only 3 mi. to DE Turf, 15 mi. to Dover, and 30 mi. to the beaches! There are open stairs, so not appropriate for small children. Well-behaved pets welcome.

4.97 out of 5 average rating, 95 reviews

Home in Greensboro

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.

Superhost

Apartment in Dover

4.87 out of 5 average rating, 268 reviews

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

4.88 out of 5 average rating, 121 reviews

Guesthouse in Dover

Country Guest House

Relax with the whole family at this peaceful place to stay on the farm. You will see horses, cows, goats, chickens & ducks. Family friendly. Animals roam the property & are safe to pet. You will hear many farm noises such as roosters crowing, cows mooing & more. This home is located in the country & a min of 5 miles from stores and shopping. Full kitchen, 1 full bathroom & 1 queen bed included. Upon request Queen Air Mattress or Twin Bed can be provided.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Henderson holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Henderson

Private room in Millington

5 out of 5 average rating, 268 reviews

Guest Suite in a Victorian on the Chester River

AnielaRating, 5 stars2 weeks ago

Our stay was perfect - like a luxury suite for a portion of the cost and no worries about other people around you making noise. Teddi is very nice and the place was super clean. Would definitely stay again and recommend!

4.91 out of 5 average rating, 23 reviews

Private room in Smyrna

Private suite with own entrance/Bathroom

NicoleRating, 5 stars2 days ago

Highly recommended staying at Yessica's! Stayed 2 night for a sports tournament with my son and felt incredibly safe in a very clean , spacious and comfortable private entrance room ! Next lacrosse tournament in the area I'll be definitely booking here again !

5 out of 5 average rating, 11 reviews

Guesthouse in Greenwood

Guest Suite, Private Entrance

GabrielleRating, 5 stars1 week ago

We stayed at Heather’s for a tournament at the DE Turf Sports Complex. It was an extremely convenient spot, very quiet and clean. We were very grateful for the bottled water and snack basket!

4.93 out of 5 average rating, 15 reviews

4#Lux King sz BR private Bathroom

MarthaRating, 5 stars3 weeks ago

Place was lovely and clean - Roxana communicated quickly whenever we had a question. We would stay here again.

4.83 out of 5 average rating, 71 reviews

Downtown Dover/DSU/King sz/FreeParking/Confort

MannyRating, 5 stars1 month ago

Mariela's place was perfect for what I needed. Definitely will be back!

5 out of 5 average rating, 37 reviews

Private room in Smyrna

Modern King size bedroom Wi-Fi, parking, kitchen

CarolineRating, 5 stars3 weeks ago

Lovely place, clean, bed is super comfy. Each room locks separately so remember to bring phone to bathroom or memorize the security code. The refrigerator is in your room which is super helpful as I had medicine to store. Although your room is private the space is shared with others. It’s luck of draw on the other people. First night there was a loud obnoxious couple , 2nd night super quiet.

4.99 out of 5 average rating, 193 reviews

'Room J' for 1-2 guests in "Black Horse Inn"

AndrewRating, 5 stars2 days ago

What a great host! They made us feel right at home and rolled out the red carpet for us. Great conversation and great privacy when needed. Good decision to stay with Renate and Bob. Will definitely stop in the next time we are in the area.