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Compare 87 Vacation Homes in Crumpton with updated reviews, rates, and availability.

"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."

"Our stay was incredible! The house is beautiful, it is super spacious with tons of perfect places to congregate and hang out. The rooms were all extremely comfortable and the beds had high quality mattresses that made sleeping so enjoyable. The views and sunsets were spectacular and our group loved spending our evenings enjoying the hot tub. The house’s location is perfect as it is not only right on the water but it’s just under one mile from the (albeit super tiny) town of Rock Hall. I’d love...

"a great place to unwind. "

"From the moment we entered the property the relaxation began!! The location and history of the area was interesting. The rooms were comfortable and homey. The screened porch was the central space and the reading knook was never empty. All enjoyed kayaking and paddle boarding in the calm river water. All agreed we would like to revisit the property again. Communication with the owners was prompt and courteous. Thank you"

AED 4,064 total

includes taxes & fees

27 Apr - 28 Apr

"This house is very nice and conveniently close to Washington College. Teddi was responsive to our last minute rental. "

"Owner/host was absolutely the best communicator. Spectacular views. The suite was an added bonus. Great beds in all the rooms . The kitchen provided great space to prepare family meals together. Wonderful water pressure. Stayed at the home for a special getaway for mom's 91st birthday. She kept stating "I love this little house". This home surpassed our expectations. This stay will forever have special memories. We hope to return. jold special memories "

"We had a great time. Place was unique and good for group get together. "

"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "

"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."

"This was the best Christmas yet and on top of that, the home was amazing, great amenities, great view, great time. Thank you to the host! "

Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "

Fridge, microwave, coffee/tea maker, toaster

"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"

AED 993 total

includes taxes & fees

28 Apr - 29 Apr

"This is our second time staying at The Lighthouse and we had a wonderful time! It is perfect for three couples. The kitchen is large and fully equipped . The living room/dining room is spacious. The house was clean and ready for us. The property manager, Diane was responsive and very helpful. "

"Property was located about 500ft from my sister and brother in laws house...sister is going through home hospice..so it was really convenient "

3 bedrooms, iron/ironing board, free WiFi, bed sheets

"We booked this home for the Waterman’s Triathlon Weekend. My wife was racing and I like to have a location close to the event so we don’t have to worry about driving/parking/commuting the morning of and this location was EXACTLY what we were looking for! This home was clean, spacious and homey! We had plenty of room for both of us to work remotely for a full day, great lounging living room and the garage access was a great perk as it gave us space to store all of my wife’s triathlon gear for...

"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."

"My family enjoyed this house so much. The place is perfect for a relaxing gateway with so much peace and nature. Will definitely be back!"

"Very nice stay for us. Clean bright space. Loved the accommodation of each room with their own lock, desk, fridge and tv. Shower, no bath but otherwise prefect for our family. Felt secure with the cameras in front and back. Was thankful for this space so close to my grandmother. "

AED 946 total

includes taxes & fees

7 May - 8 May

"Our family stayed at this beautiful home for the weekend. Communication was flawless and easy. The home was perfect for family gathering in different rooms in the home (and great outdoor spaces!) as well as spacious bedrooms. Everything was clean and well, perfect. We will be coming back!"

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Other property types in Crumpton

AED 993 total

includes taxes & fees

28 Apr - 29 Apr

"Great little home away from home. A small orientation list for newcomers would be helpful. Closest groceries, gas and such. Outside of that all and all VERY pleasing. "

Recent reviews of Crumpton hotels

5/5 Excellent

"Was in Middletown for a funeral. The Hampton Inn was a convenient location. The property was clea,quiet and safe. Breakfast was free."

A verified traveler stayed at Hampton Inn Middletown

Posted 3 days ago

5/5 Excellent

"Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!"

A verified traveler stayed at Comfort Inn & Suites Chestertown

Posted 2 weeks ago

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

5/5 Excellent

Peaceful rest and relaxation!

"Clean and away from all the hustle and bustle, not to mention the views and lovely hosts! Don’t miss out on this if you want a relaxing trip, or if you do want to explore the area there’s plenty of great small towns in the area, also an easy drive to some of the most iconic cities along the Chesapeake Bay."

A verified traveler stayed at WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Posted 3 weeks ago

5/5 Excellent

Great place for a couples retreat or family

"The Inn at Huntingfield Creek is clean, well-appointed and peaceful. Management communicated prompty via texts. The Inn serves breakfast. We were looking forward to it on Sunday, in the well-appointed and cozy main lodge but, much to our dismay, the food ran out, or so we were told. Beakfast was wrapped up in an hour (served from 830 to 930 am) and we missed it. It would have been nice to get a cup of coffee and something light to enjoy on a lazy Sunday but we missed out. Other than this minor gripe, the Inn is delightful."

A verified traveler stayed at Inn at Huntingfield Creek

Posted 3 weeks ago

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

5/5 Excellent

Beautiful bay front property

"Wonderful stay for 75th and 50th birthday celebrations.Everyone from age 4 to 75 had a terrific time. So much to do we did not leave the property. View of the Chesapeake Bay is amazing - from sunrise to gorgeous sunsets. Plenty of room for everyone. Great communication from host with instructions and area suggestions. 5 Star"

A verified traveler stayed at Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Search Vacation Homes in Crumpton

Plan, book, stay with confidence

Check prices for these dates

Compare 87 Vacation Homes in Crumpton with updated reviews, rates, and availability.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Waterfront family resort Lodge with private pier, game room and bar

Waterfront family resort Lodge with private pier, game room and bar

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Stay in the landmark Lighthouse!

Stay in the landmark Lighthouse!

Entire Townhouse in Rock Hall

Entire Townhouse in Rock Hall

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking

Welcome to Mermaid Haven! The perfect spacious home for your Rock Hall vacaction

Welcome to Mermaid Haven! The perfect spacious home for your Rock Hall vacaction

Other property types in Crumpton

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Stay in the landmark Lighthouse!

Stay in the landmark Lighthouse!

Recent reviews of Crumpton hotels

Recent reviews of Crumpton hotels

Hampton Inn Middletown

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