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Chesapeake Dream: 5 Bedroom Vacation Accommodation in Cambridge MD

Home Rental in Cambridge Maryland

Chesapeake Dream is a 5 bedroom home for rent on the Eastern Shore of Maryland. The property is packed with amenities and sleeps 12 comfortably.

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Wander Home
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Rates from
$523 / night
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Rental overview

Why You'll Love This Rental

Chesapeake Dream is a renovated waterfront farmhouse in Cambridge, Maryland on the Eastern Shore, set on 5.6 acres with Chesapeake Bay views. The 2,400-square-foot home sleeps up to 12 guests across 5 bedrooms, with 3 full bathrooms and 1 half bath. Standout features include a private waterfront with dock access, a seasonal heated swimming pool (optional heating fee), and multiple outdoor gathering areas including a screened porch, balcony seating, and a bayside fire pit.

Inside, the home is fully air conditioned and heated and includes high-speed Wi-Fi, a gas fireplace, and a Sonos Bluetooth sound system. The kitchen is stocked for cooking with a large island, stainless steel appliances, and both a coffee pot and Keurig. Sleeping is arranged across three levels, including a king master suite with an en suite bathroom, soaking tub, and shower, plus a loft/kids bedroom with a double bed and three twin beds. Practical extras include washer/dryer, linens and towels, children’s books and toys, two Pack ’n Plays, and driveway parking for up to 10 vehicles.

Good fit for
Fishing trips Boating stays
Waterfront with dock Private waterfront access includes a dock; guests may use the dock but not the boat lifts.
Seasonal heated pool Private pool is available April–October, with optional paid heating.
Outdoor kitchen setup Outdoor kitchen includes a gas grill and refrigerator for poolside meals.
King primary suite Primary bedroom has a king bed, TV, and en suite bath with soaking tub and shower.
Kayaks provided Two kayaks with paddles and life jackets are available seasonally.
At a glance

Property Highlights

5 BedroomsBedrooms
3 Full, 1 Half BathroomsBathrooms
Sleeps 12Guest Capacity
2400 sq. ft.Living Space
Pool, Pool (Private)Pool
Internet AccessInternet
TelevisionTelevision
YesAir Conditioning
YesWasher / Dryer
Location & nearby Explore the Area

This home is in Cambridge, Maryland on the Eastern Shore, with a quiet, private setting on the Chesapeake Bay. The property offers on-site access to the bay and dock, and the host notes that a car is needed to go anywhere off the property. Uber and taxi service may be available in the area but can involve long waits or be difficult to find.

Plan your stay

Rates & Availability (USD)

Rates from
$523 per night
2-day minimum stay
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Live booking details are maintained by Wander Home.

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About this rental

About This Rental

Chesapeake Dream is a 5-bedroom, 3.5-bath waterfront home in Cambridge, Maryland, offering 2,400 square feet of indoor space and room for up to 12 guests. The property sits on 5.6 acres and is oriented around Chesapeake Bay views, with outdoor spaces designed for time on the water and relaxed evenings outside. Guests have access to the dock and bay (boat lifts are not for guest use), along with a private seasonal swimming pool that can be heated for an added service fee and nightly charge.

Outdoor amenities include a screened porch, an open-air balcony with seating, a wood-burning fire pit, and an outdoor fireplace (firewood provided). There is also an outdoor kitchen setup with a gas grill and refrigerator, plus patio/balcony seating and a hammock. Two kayaks, paddles, and life jackets are provided seasonally. A seasonal pool house bathroom with a shower is also listed.

The interior includes central air and split units for heating/cooling, a gas fireplace, high-speed Wi-Fi, TV, and a sound system. The kitchen is equipped with a farmhouse sink, large island with stool seating, stainless steel appliances (including dishwasher), and small appliances such as a microwave, air fryer, slow cooker, toaster, and blender. Essentials such as linens, towels, shampoo/conditioner/body wash, and basic cleaning and laundry supplies are provided.

Sleeping is arranged over multiple floors: three queen bedrooms, a king primary suite with en suite bath, and a loft/kids bedroom with one double bed and three twin beds. Self check-in is via keyless entry, and driveway parking is available for up to 10 vehicles. The home has quiet hours (10pm–7am) and does not allow pets.

Summary

Chesapeake Dream is a stunning renovated waterfront farmhouse on 5.6 acres with breathtaking Chesapeake Bay views — perfect for families & friend groups. Boat, fish, crab & hunt at this outdoorsman's paradise. Watch the sunset from the screened porch, gather around the bayside fire pit, or BBQ poolside. With historic landmarks, hiking, golf & charming towns nearby, every day brings a new adventure.

Hosted by Wander Home - see "Other Things To Note" in the description below.

Space

SPECIAL AMENITIES & SPACES:
● Chesapeake Bay views from all over the house & property!
● Private waterfront w/ dock - bring your boat (public boat ramps nearby)
● Excellent location for fishing, crabbing, deer & duck hunting, & bird watching - bring your gear to do all on the property or book with nearby guides & excursions
● Private Swimming Pool (Available Apr - October. Dates subject to change).
● Large screened porch & open-air balcony w/ outdoor seating
● Wood-burning fire pit & outdoor fireplace (w/ firewood provided)
● Outdoor kitchen w/ gas BBQ grill & fridge
● Master bedroom suite w/ king bed, TV, soaking tub & shower
● Fully air conditioned and heated - central air system & split units
● Gas fireplace
● High-speed Wi-Fi
● Sonos bluetooth sound system
● Fully stocked & equipped kitchen

OTHER FEATURES:
● Outdoor pool house bathroom w/ shower (seasonal)
● Hammock & swing
● 2 Kayaks and 3 paddles w/ life jackets (seasonal)
● Coffee pot & Keurig w/ coffee pods & grounds
● Board games, puzzles & books
● Children's toys & books
● Washer & Dryer
● Telescope
● Ceiling fans
● 2 pack 'n plays

SLEEPING ARRANGEMENT:
1st Floor
● Living Room - large sofa

2nd Floor
● Bedroom 1 - 1 queen bed w/ ceiling fan & closet
● Bedroom 2 - 1 queen bed w/ ceiling fan
● Bedroom 3 Master Suite - 1 king bed w/ en suite bathroom, TV, closet, & dresser

3rd Floor/Loft
● Bedroom 4 - 1 queen bed w/ dresser
● Loft/Kids Bedroom - 1 double bed & 3 twin beds

KITCHEN:
● Farmhouse sink
● Large island w/ stool seating
● Stainless steel appliances - fridge/freezer w/ water dispenser & ice maker, gas stove/oven, dishwasher
● Mini fridge for drinks
● Microwave, air fryer, toaster, slow cooker, & blender
● Coffee pot & Keurig single serve
● Cooking & baking basics
● Tableware & cutlery
● Basic spices
● Grilling utensils

ESSENTIALS & EXTRAS:
● Linens, pillows & towels
● Shampoo, conditioner & body wash
● Laundry detergent, dishwasher detergent & dishwashing soap
● Clothing storage: dressers, closets, & luggage racks
● First aid kit
● Hair dryer
● Basic cleaning supplies

Access

● Self-check-in with keyless entry - Access code will be sent out once the rental agreement is signed
● Driveway parking for up to 10 vehicles
● Early check-in and late-check out may be accommodated for a fee ($100 each). Please contact us to see if we can accommodate your request. Payment will only be collected once we confirm that your request can be accommodated.
● Guests have access to the dock (boat lifts are not for guest use), bay, and swimming pool (seasonal). Access these amenities and swim at your own risk.

Neighborhood

The property is a quiet, private retreat, but the nearby area has plenty to offer - including downtown Cambridge, local hunting and fishing guides, American history, fresh seafood, outdoor activities, and water sports. It is also within 1 hour of the towns of St. Michaels, Easton, and Salisbury, and within 2 hours of Ocean City, Chincoteague, Assateague, and the Delaware beaches. Below are a few highlights:

5 minute drive to:
● Soft & Salty Seafood Market
● Danny's Soft Crabs restaurant & market
● Ragged Point boat ramp

10 minute drive to:
● Neck District Grill

20 minute drive to:
● Downtown Cambridge
● Ironman Maryland
● RaR Brewing
● Blue Ruin restaurant
● The Dive Club bar & restaurant
● Ava’s Pizzeria & Wine Bar
● Choptank Oyster Company
● Cambridge Skeet & Gun Club
● Gerry Boyle Park and Boat Launch
● Choptank River Lighthouse
● Cambridge Farmers Market at Long Wharf

25 minute drive to:
● Choptank River Lighthouse
● Long Wharf Park
● Carmela’s Cucina
● Portside Seafood Restaurant
● Choptank River Crab & Oyster Co. seafood market
● Emily's Produce market
● Little Blackwater Soft Launch & Water Trail
● Sailwinds Park & Playground
● Dorchester County Visitor Center

30 minute drive to:
● Blue Point Provision Company restaurant
● Blackwater Adventures - Hyatt location
● River Marsh Golf Club
● Rise Up Coffee
● Breckenridge Barn wedding venue

35 minute drive to:
● Harriet Tubman Underground Railroad National Historical Park
● Blackwater National Wildlife Refuge Visitor Center
● Blackwater Adventures Chesapeake Bay
● Marsh Edge Hiking Trail
● Layton's Chance Vineyard & Winery

Transit

● You will need a car to go anywhere off the property. Uber and taxi cabs are available in the area, but can have long wait times or be difficult to find.

Notes

For specials, promotions, deals and additional availability please contact our team at Wander Home Poconos.

● The rental agreement will be sent to you once the reservation is accepted. Your booking is only confirmed once it is signed. Kindly complete it within 24 hours to secure your reservation.
● This property can host a maximum of 12 guests, including children and infants, per the local governing regulations.

POOL INFORMATION:
● The pool is cleaned prior to your arrival. As the pool is outdoors, leaves and other natural debris may occasionally accumulate during your stay. A pool skimmer is provided for guest use.

● Wander Home requires that all guests have their profile 100% verified. Please upload government issued ID and payment method in your account settings, as well as sending us a photo of your ID.
● Eligible refunds are subject to a 6% processing fee.
● A damage waiver fee ($50) is included for all reservations. Most booking channels add this upfront. Others do not have this capability, and it will be manually added to the invoice once the reservation is confirmed.
● We provide enough essential items to cover stays of about 2-3 nights. If you need more supplies during your stay, you can drive 25-minutes into the town of Cambridge for stores like Walgreens, Aldi, Food Lion, & Family Dollar.
● Given the rural setting of the property, occasional sightings of ants, spiders, flying insects, and mice may occur despite our year-round pest control efforts. We strive to manage these encounters to the best of our ability, but cannot guarantee that the house will be completely pest free.
● When drought, weather or other conditions present an unusual fire risk, a burn ban may be imposed by the local jurisdictions without prior notice.

SECURITY CAMERAS / AUDIO RECORDING DEVICES:
● 1 doorbell camera at the front entry door
● 3 additional security cameras around the exterior of the property: front porch facing driveway, pool deck, rear porch facing bay

InteractionWithGuests

● We are here for you during your stay, but our level of interaction is up to you. We are only a phone call or message away. You and your party will be able to self check-in upon arrival.
● Please remember that you are staying in a house, not a hotel. Please treat the space with respect. If any problems arise we will do our best to take action ASAP, but there is no one living on-site 24/7.

HouseRules

By booking our home, you confirm you agree to our house rules, additional fees & completing the rental agreement.

● Must be at least 21 years old to book this property
● This property can host a maximum of 12 guests, including children and infants, per the local governing regulations.
● Quiet Hours: 10pm to 7am - please be respectful of the neighbors and keep noise to a minimum during these times, especially when enjoying the outdoor amenities.
● No pets
● No unregistered guests allowed - All visitors must be approved by Wander Home
● No unapproved parties or events
● No fireworks
● Swim at your own risk
● Guests have access to the dock, but boat lift access is not permitted
● Must have valid state required boating, fishing, & hunting licenses to perform these activities
● Flush only toilet paper down toilets
● Trash - All trash must be bagged and placed in the trash cans at the end of the driveway
● Dishes - Wash all dishes, or fill and turn on the dishwasher when you check-out
● If you open it, close it. If you borrow it, return it. If you turn it on, turn it off. If you break it, fix it. If you use it, take care of it. If you make a mess, clean it up. If you move it, put it back.
● Respect the local habitat. Practice 'leave no trace' and 'pack it in, pack it out.'
● Penalty: $500 for unauthorized late checkout
● Penalty: $500 minimum fine for breaking any of our house rules

What's included

Property Amenities

Featured Amenities

Air Conditioning
Grill
Dishwasher
Washer/Dryer
Fireplace
Internet Access
Pool
Pool (Private)
Television

Property Features

Towels/Linens
Blender
Ceiling Fan(s)
Coffee Maker
Parking
Freezer
Hair Dryer
Ice Maker
Microwave
Refrigerator
Oven
Stove
Toaster

Entertainment

Board Games

Other Property Amenities

Baking sheet, Bathtub, Boat slip, Carbon monoxide detector, Children’s books and toys, Cleaning Disinfection, Cleaning products, Clothing storage, Coffee, Conditioner, Cookware, Dining table, Dishes and silverware, Dryer in common space, Enhanced cleaning practices, Essentials, Extra pillows and blankets, Family/kid friendly, Fire Pit, Fire extinguisher, First aid kit, Fishing, Garden or backyard, Golf - Optional, Hammock, Hangers, Heating, High touch surfaces disinfected, Horseback Riding, Hot water, Kayak, Kitchen, Laundromat nearby, Long term stays allowed, Museums, Near Ocean, Ocean Front, Outdoor kitchen, Outdoor seating (furniture), Pack ’n Play/travel crib, Patio or balcony, Private entrance, River, Room-darkening shades, Sea view, Shampoo, Shopping, Shower bench, Shower gel, Smoke detector, Sound system, Suitable for children (2-12 years), Suitable for infants (under 2 years), Water Sports, Water View, Waterfront, Wine glasses
Helpful details

Frequently Asked Questions

Chesapeake Dream is located in Cambridge, Maryland.

Chesapeake Dream accommodates up to 12 guests.

5 Bedrooms and 3 Full, 1 Half Bathrooms.

Yes. The property lists Pool, Pool (Private).

The property lists a 2-night minimum stay.

Chesapeake Dream is professionally managed by Wander Home.
Local management

Professionally Managed By

Wander Home View Manager Profile

Questions about this rental?

Connect directly with Wander Home for current rates, availability, and local assistance.

Contact Wander Home Reservations and Guest Services
Daytime Phone Evening Phone Text Number
Property reference
#185424 · Chesapeake Dream
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