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Vacation rentals in Henderson

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Henderson

Guests agree: these stays are highly rated for location, cleanliness, and more.

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A light-filled living area features blue paneled walls and contrasting wooden accents. A spacious sectional sofa and a classic armchair are situated around a low coffee table. The open layout provides visibility towards the kitchen and dining space, enhancing the feeling of connectivity.
Home in Centreville
4.73 out of 5 average rating, 98 reviews

Historic Centreville Home

Historic and very charming home! Built in 1881 with modern touches. 1200 sq feet home. Fully fenced-in, spacious backyard. Very open kitchen/living room area with passthrough to view TV from kitchen. Tree house w/electricity! Approximately 300 yard walk from the Wharf (public landing). Four kayaks and two paddle boards available for your own use! 80 yard walk to the most popular restaurant in town, Doc's. Walking distance to downtown Centreville and Millstream Park trail. Fireplace does not work

Top guest favourite
The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.
Apartment in Greenwood
4.97 out of 5 average rating, 633 reviews

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)

Superhost
A small porch features two teal rocking chairs positioned in front of a beige exterior with red shutters. The entrance is marked by two red doors, with light illuminating the area and a porch railing leading the way.
Apartment in Dover
4.76 out of 5 average rating, 62 reviews

Farm house Oasis

Relax with the whole family at this peaceful place to stay. This 1st floor unit, located on a gated farm, has 2 bedrooms and 1 bathroom and can sleep up to 6 people. If you enjoy the outdoors then this is the place for you. We have walking paths for you to enjoy and make sure to say hi to the animals as you walk by. Sit out on the front porch and watch the sunset or sit out by the pond and watch it there. This unit is 10 minutes from the nearest shopping. Do not enter barns or pastures.

Top guest favourite
A spacious studio interior features a king bed positioned near a sloped ceiling. A seating area includes a gray sofa and a recliner, complemented by a coffee table. A wooden dining table is set for two, and large windows provide ample natural light.
Apartment in Chestertown
4.96 out of 5 average rating, 254 reviews

Chestertown Private cottage with NFL Sun Ticket

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.

Top guest favourite
Home in Centreville
5 out of 5 average rating, 48 reviews

Lansdowne Manor | Firepit | BBQ | Pets | 198 Mbps

Historic country manor located in a private tranquil setting, surrounded by mature trees & nature. ★ "An absolutely amazing property—graceful, historical, and very well cared for." ☞ Deck w/ BBQ + fire pit + dining ☞ Spacious backyard w/ lush views ☞ Fully equipped + stocked kitchen ☞ Parking → driveway (4 cars) ☞ Onsite washer + dryer ☞ 55” + 43” smart TVs ☞ 198 Mbps wifi ☞ Pet friendly 9 mins → DT Centreville (cafes, dining, shopping) 13 mins → Tuckahoe State Park hiking trails

Top guest favourite
A spacious home is presented, featuring a combination of stone and siding on the exterior. Large windows provide ample natural light, while a covered porch offers a welcoming entrance. The surrounding landscape consists of open fields and a clear blue sky.
Home in Harrington
5 out of 5 average rating, 14 reviews

Welcome to the Redbird Retreat!

Escape to this secluded home with stunning views, abundant wildlife, and tranquil ponds. Situated on a working farm. The spacious home features three bedrooms, including a king suite, a queen room, and a full-size bunk bed. Enjoy two fireplaces, a large kitchen with an island, cozy reading nooks, and a large deck overlooking farmland. Perfect for relaxation or adventure, with nearby Harrington Raceway and Casino. Experience peace, comfort, and nature all in one beautiful location.

Top guest favourite
A cabin nestled among tall trees presents a rustic appearance. A flowering garden features pink blooms and lush greenery, complementing a wooden fence. The cabin's dark exterior contrasts with the vibrant natural surroundings, creating a serene atmosphere.
Cabin in Greenwood
4.93 out of 5 average rating, 14 reviews

Mast Cabin

Enjoy a peaceful stay in our cabin set in the edge of the woods. The cabin is 100 feet from our house, and has its own gravel driveway along the woods. We are located in a rural area on 8 acres . You are welcome to explore and enjoy our property. We are located 30 miles from Delaware beaches. When requesting to book, please include a brief message telling us who is coming (max 2 guests) and the purpose for your travel plans. Requests without this basic info won’t be approved.

Top guest favourite
A single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.
Home in Greensboro
4.96 out of 5 average rating, 112 reviews

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.

Top guest favourite
A comfortable sitting area features a green sofa, two blue armchairs, and a wooden rocking chair. Natural light filters through a large window draped with sheer curtains, illuminating the warm wooden paneling and area rug. A round coffee table sits in the center.
Guesthouse in Camden
5 out of 5 average rating, 38 reviews

The little backyard guest house

A little hideaway only a few miles away from Dover, Dover Air Force Base, Dover Speedway and Dover Downs. The beaches are only 45 mins away with great restaurants and shopping. This AirBnB is located in the historic district of Camden situated in the backyard of a private home. You have your own private building! There are stairs up to the deck as the guest house is on the second floor. Please note there is no WiFi or TV.

Guest favourite
An open-plan attic-style space features a well-equipped kitchen area with white cabinetry and modern appliances. A comfortable sofa bed and a coffee table are arranged beside a large window, allowing natural light to fill the room. Light blue walls complement the wooden ceiling beams.
Apartment in Camden
4.92 out of 5 average rating, 24 reviews

Cozy & Spacious Studio Apartment

Enjoy a short drive to downtown Camden or the city of Dover. Visit local attractions such as the John Dickinson Plantation, Bombay Hook National Wildlife Refuge, Biggs Museum of American Art, and the Delaware Agriculture Museum. For a night out, try your luck at Bally's. Take a day trip to the beaches in Rehoboth or historic Lewes or travel north to see the Longwood Gardens or the beautiful estate at Winterthur.

Guest favourite
A comfortable living area features two dark brown sofas positioned around a glass-top coffee table. Natural light filters through sheer curtains, illuminating the space. A potted plant and decorative wall art enhance the ambiance, while a wall clock adds a functional element.
Apartment in Dover
4.88 out of 5 average rating, 166 reviews

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.

Guest favourite
The studio apartment features a spacious layout with a king bed and a bunk bed. Light-colored walls complement the wooden flooring. A flat-screen TV is mounted on one wall, with a dresser and bedside table positioned nearby. Natural light illuminates the room through recessed lighting.
Apartment in Frederica
4.97 out of 5 average rating, 75 reviews

The Indian Point B&B

A cozy 1 bedroom studio apartment with a full bathroom and kitchen located in downtown Frederica, DE. This space has its own private entrance so that you can come and go as you please. This apartment is 2.5 miles from Delaware Turf Sports Complex, 9 miles to Dover Air Force Base and 30 miles from Delaware beaches. Route 1 freeway access is an easy 1/2 mile from the apartment.

Popular amenities for Henderson vacation rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Caroline County
  5. Henderson