Vacation rentals in Crumpton

4.95 out of 5 average rating, 141 reviews

An open staircase with wooden steps leads to a second-floor catwalk, surrounded by large windows offering views of the outdoors. Natural light fills the space, illuminating the warm wood tones of the staircase and the nearby lush greenery visible through the glass.

Farm stay in Chestertown

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Guest suite in Chestertown

An enclosed screened porch is illuminated with soft, warm lighting, creating a welcoming atmosphere. Multiple windows offer expansive views, while a seating area is visible inside. Stairs lead up to the porch, surrounded by lush greenery and brick accents.

4.98 out of 5 average rating, 165 reviews

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)

Guest suite in Chestertown

Two comfortable adirondack chairs are positioned on a wooden deck, facing a scenic view of a tidal creek surrounded by trees. A small black table sits between the chairs, offering a space for refreshments while enjoying the natural surroundings.

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.

4.97 out of 5 average rating, 129 reviews

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.

4.94 out of 5 average rating, 178 reviews

Cottage in Charlestown

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

4.97 out of 5 average rating, 587 reviews

A white pygmy goat balances on a wooden plank set atop a spiral post, surrounded by autumn foliage. A white fence separates the goat from the grassy area, while leaves cover the ground beneath, showcasing the colors of fall.

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)

Casa particular in Chestertown

An inground pool is surrounded by brick paving, with several lounge chairs positioned nearby. The pool's turquoise water is partially shaded by a large tree, providing a serene outdoor setting. Lush green grass and a wrought-iron fence are visible in the background.

4.92 out of 5 average rating, 148 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

4.97 out of 5 average rating, 236 reviews

A wooden bridge crosses over a lush green landscape, leading towards a two-story building nestled among trees. The property is surrounded by vibrant greenery and features a variety of foliage, creating a serene outdoor environment.

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.

5 out of 5 average rating, 26 reviews

Two Adirondack chairs are positioned invitingly on a wooden dock that extends over the calm water. The dock features sturdy posts and a seamless surface, reflecting the surrounding greenery and serene atmosphere of the riverside.

Home in Millington

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!

5 out of 5 average rating, 110 reviews

A private rooftop deck is presented with a round table and two ornate chairs, surrounded by potted plants. The view features abundant trees and the river in the background, creating a serene outdoor space.

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!

4.88 out of 5 average rating, 122 reviews

An outdoor patio features a shaded table and chairs under a large red umbrella. The landscape includes open grassy areas, with trees in the background. A pathway leads from the patio toward the lush greenery, connecting to other buildings in the distance.

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.

Superhost

5 out of 5 average rating, 4 reviews

Relaxing Waterfront - Golf Course & Sunset Views

Our home away from home in Chestertown is truly an extraordinary property. Water and golf course views from every room. And wildlife! Some of the birds and animals we've seen: - blue herons - bald eagles - ospreys - ducks - turtles - otters Inside, there's room enough for 8, with 3 bedrooms and 3 full bathrooms, including one of each on the main level. Just one mile from downtown Chestertown, and a short walk to Chester River Yacht & Country Club

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Popular amenities for Crumpton vacation rentals

Kitchen

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Crumpton

A spacious two-story home is surrounded by lush green lawn and mature trees. A stone path leads to its welcoming entrance. Large windows reflect sunlight, offering views of the nearby water. The serene setting is enhanced by the gentle presence of the surrounding nature.

4.99 out of 5 average rating, 107 reviews

Entire River Front Home - 4 Bedrooms 4.5 Baths

JeanneRating, 5 stars13 months ago

We had a wonderful stay at this beautiful place. Our extended family and dogs thoroughly enjoyed the private and peaceful location. Bobs place was provisioned very well. We appreciated the numerous coffee cups, wine glasses, etc. it felt very much like staying with family. Lovely art throughout too.

5 out of 5 average rating, 33 reviews

A modern kitchen space features a dark granite countertop with seating, highlighted by stylish light fixtures. The dining area includes a round table with four chairs, situated beside large windows that allow natural light to fill the room.

Home in Joppatowne

Two bedroom small ranch with beautiful forest view

JosefinaRating, 5 stars2 days ago

This listing was immaculately clean, beautifully decorated and very organized. The area was quiet and beautiful. Neighbors in the area very nice. They offered all the basic and necessary amenities needed and more. Our overall experience was GREAT and we definitely would rent this location again.

Home in Millington

4.9 out of 5 average rating, 39 reviews

The Grey Goose by the Chester River

BaraniRating, 5 stars11 months ago

I couldn't have asked for a better place to have a family reunion. The dining room and living room was the day center for the weekend. People were able to relax and enjoy reconnecting. I loved the treeline driveway facing the small church. Yoga on the porchnin the morning was sublime.

A welcoming front porch is featured, with a vintage-style bench resting against the wall. Windows adorned with shuttered frames allow natural light to flow in. A potted plant with vibrant flowers adds a touch of color. The porch flooring is finished with a warm red hue.

5 out of 5 average rating, 13 reviews

High Tide & Hound

RickRating, 5 stars1 week ago

One of the cuties places we have stayed. This was a perfect place and set up appropriately for our 3 year old granddaughter and our fur baby. Jessica had also left some snacks which we were so thankful for after the drive. Thanks for a wonderful experience.

5 out of 5 average rating, 37 reviews

Farm stay in Centreville

No Fees~Historic Lansdowne Manor

AndrewRating, 5 stars2 months ago

I had a wonderful stay at the Manor. Alex was an exceptional host—very responsive and accommodating throughout my visit. The manor is beautiful, featuring a charming vintage appeal perfectly complemented by modern amenities. It felt both timeless and comfortable. Conveniently, grocery stores and restaurants are just a short drive away, which made my stay even more enjoyable. Overall, it was a fantastic experience, and I would love to stay again.

4.93 out of 5 average rating, 42 reviews

A charming two-story house features a gabled roof and a welcoming entrance surrounded by vibrant greenery. Tall evergreen shrubs line the path, and a wooden porch with white railings invites guests to explore the home. Natural light filters through the windows, highlighting the house's character.

Cottage in Centreville

Captain’s Quarters - Unique home on Corsica River!

LoriRating, 5 stars10 months ago

An incredibly peaceful setting, we enjoyed time on the main floor deck watching the wild life and river! A perfect place to reflect with a good cup of coffee in hand!