Plan your trip

some people from above sitting at a small city park green

Crumpton Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

  • Check prices for these dates

    Check prices for these dates, December 15 – 16, 2026

    View in a map

    Our top choices for Crumpton vacation rentals

    1. Guest Suite for up to 2 in a Victorian on the Chester River

    A person sitting on a wooden deck by a calm body of water, surrounded by greenery.

    2. Newly restored apartment in the heart of Chestertown

    A spacious living area with a dining table, sofa, and a kitchen in the background.

    3. First Floor Studio Apartment in Historic Chestertown

    A house with a swimming pool, surrounded by a fence, and two red umbrellas.

    4. Peaceful Farmhouse Getaway on a Working Farm

    A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

    5. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

    A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

    6. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

    A wooden staircase leading to a beach with a clear view of the sea.

    7. Turtle Cove Room

    An aerial view of a property with a large house surrounded by lush greenery, a driveway, and a road nearby.

    8. Beachcomber Suite

    A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

    9. Family Retreat at Lansdowne Manor

    An outdoor patio with a brick wall, a grill, and metal chairs.

    10. Bohemia Manor Farm

    Beach bar

    11. BAYSIDE BUNGALOW

    A house with a front porch, a pathway leading to the entrance, and a bicycle parked outside.

    12. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

    A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

    13. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

    A modern living room with a flat-screen TV, a brown sofa, a dining table with placemats, wicker chairs, and a kitchen area with a microwave and stove.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

    View all properties

    Find vacation rentals that suit your style

    Apartments

    Condos

    Cottages

    Top Crumpton Hotel Reviews

    Comfort Inn & Suites Chestertown

    A hotel lobby with a fireplace, seating area, and a television.

    Holiday Inn Express & Suites Middletown by IHG

    A lobby area with seating, a reception desk, and a refrigerator stocked with beverages.

    Fairfield Inn & Suites by Marriott Middletown

    A modern living room with a stone accent wall, a flat-screen TV, a dining area with a table and chairs, and a sofa with cushions.

    Hampton Inn Middletown

    A hotel dining area with a long wooden table, six chairs, and a fruit bowl.

    Inn at Huntingfield Creek

    A boat deck with a white bench and a view of a calm lake and distant trees.

    Quality Inn Smyrna

    A breakfast buffet with a variety of food items and a bowl of fruit.

    Relax Inn Smyrna Dover Coastal Gateway

    A hotel room with a large bed, a black leather sofa, a wooden table, two bedside tables with lamps, and a wall-mounted air conditioner.

    Find out more about Crumpton

    Everything you need to know about Crumpton vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Crumpton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Crumpton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Crumpton vacation rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Crumpton. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Crumpton in high season.

    Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $116 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

    How to find incredible deals on Crumpton rentals

    At Expedia, we put the best Crumpton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Crumpton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Crumpton vacation.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Crumpton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Are there vacation rentals in Crumpton?

    Yes, we give you a choice of vacation rentals close to popular local attractions in Crumpton, or you can choose a secluded option if you want a relaxing place to stay.

    What are some of the best vacation home rentals that Crumpton has to offer?

    The Colonial Farmhouse with Private Boat Rental: This vacation home near Crumpton offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

    What’s there to see and do in Crumpton?

    Explore the area and family-friendly sights such as Crumpton Auction, or get out into nature at a spot like Betterton Beach. In the larger area, you’ll find Crow Farm and Vineyard and Rolphs Wharf Marina.

    What’s a vacation rental in Crumpton like?

    Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Crumpton. Vacation rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for small groups.

    Explore a world of travel with Expedia