Holiday rentals in Crumpton

4.95 out of 5 average rating, 141 reviews

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

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

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, 128 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

Flat 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

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!

4.93 out of 5 average rating, 58 reviews

Home in Kennedyville

Comfy and Cozy on the Eastern Shore

Tucked in a quiet, family oriented neighborhood on Maryland's Eastern Shore, this is perfect for a weekend get away or a hunting trip. Bright, cheery bedrooms and a well equipped kitchen. 7 miles from Chestertown will have you enjoying the unique shops, restaurants, and waterfront. Relax on the patio after grilling out. By booking, you agree to follow all rules. Home is not appropriate for children under 8. Guest assumes responsibility for any and all injuries children may experience.

4.97 out of 5 average rating, 236 reviews

Flat 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

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!

Serviced apartment in Chestertown

5 out of 5 average rating, 110 reviews

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, 121 reviews

Guest house 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.

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Other great holiday rentals in Crumpton

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.

4.93 out of 5 average rating, 45 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

MaxRating, 5 stars3 weeks ago

This was my second time staying here with my family and dogs. We absolutely love the property and area! We enjoyed kayaking and are dogs enjoyed swimming and playing along the river. Ina was a great host and was responsive to our needs. It was a great experience and vacation!

5 out of 5 average rating, 32 reviews

Home in Joppatowne

Two bedroom small ranch with beautiful forest view

KatherynRating, 5 stars3 days ago

We had a perfect stay! The house is very clean and neat. Had every amenity we could have needed. We stayed in town for a nearby lacrosse tournament for 3 nights. It was a perfect place to unwind at the end of the day with great AC! Having laundry on site was particularly helpful. Highly recommend!

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.

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.