Home Vacation Rentals By Owner In Cambridge, MD

Showing 92 Of 92 Vacation Rentals
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Exceptional(7)

$212.0

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Condo

Station House East: Upscale Loft in the Historic District Cambridge, MD

Cambridge, Maryland, United States

brStep into style and comfort in this beautifully appointed 1-bedroom, 1.5-bath condo located in the iconic Four Corners Building, a cherished historic landmark in the heart of downtown Cambridge, Maryland. Whether you’re visiting for a weekend getaway, remote work retreat, or a longer stay to explore the Eastern Shore, this light-filled, professionally designed condo is the perfect home base.brbrThe SpacebrInside, you’ll find high ceilings, oversized windows, and rich architectural details that highlight the building’s character, blended seamlessly with modern upgrades and thoughtful touches throughout.brbrSpacious bedroom with a plush king bed and en-suite full bathbr1.5 bathrooms – full bath attached to the bedroom and an additional half bath for guestsbrbrFully stocked gourmet kitchen with stainless steel appliances, cookware, dinnerware, coffee maker, spices, and more—everything you need to cook and entertainbrComfortable private workspace with desk and ergonomic chair—perfect for remote work or writingbrOpen living/dining area with cozy seating and a smart TVbrAll linens, towels, and essentials providedbrSecure building with easy, contact-free entrybrbrLocation, Location, Location! Step out your front door and you’re in the heart of the historic district—just blocks from the Cambridge Marina, Choptank River waterfront, and Long Wharf Park.brbrYou’re surrounded by the best of Cambridge:brWalkable to multiple pubs, wine bars, and restaurantsbrSurrounded by art galleries and local boutiquesbrJust steps from the farmers market and seasonal eventsbrMinutes to kayak rentals, boat launches, and nature trailsbrClose to the Harriet Tubman Museum & Education Center, historic churches, and other landmarksbrbrPerfect For:brCouples' getawaysbrWork-from-anywhere staysbrSolo travelers or writers retreatsbrEastern Shore adventuresbrFood and art loversbrbrThis quiet, secure, and stylish retreat offers the charm of historic Cambridge with all the modern comforts you expect. Come stay with us and experience the best of Maryland’s Eastern Shore—right outside your door.brbrNeed more space Ask about booking the adjacent unit to create a 2-bedroom, 2.5-bathroom setup. There are an additional 2 units that sleep up to 12 in the neighboring building. We are happy to accommodate weddings, corporate events, remote workers, and families!
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Bath 1

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Sleep 4

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Exceptional(2)

$483.08

/ Nightly
Private Vacation Home

Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge

Cambridge, Maryland, United States

Escape to this stunningly renovated 5-bed waterfront home on Hudson Creek in Cambridge, MD. Perfect for both luxury seekers and casual travelers, this spacious retreat offers modern amenities, high-end finishes, and breathtaking creek views. Relax in the open living spaces, cook in the gourmet kitchen, or enjoy the serene outdoor areas. Minutes from town, but offering peaceful seclusion, it’s the perfect balance of comfort and style for families, friends, or anyone seeking a memorable getaway.brbrLooking for a retreat from DC or Baltimore Come getaway to peaceful nature, enjoy the history and wonders of Cambridge, relax, and enjoy.brbrAre you an outdoorsman Go fishing and crabbing off the deep pier. Enjoy the fantastic seasons for Sitka deer, Canada Goose, Light Goose, Ducks, Waterfowl, etc.brbrHave a boat Drop in the nearby community ramp and tie up on my pier.brbrAre you made of iron Only 20 min to the start of the annual Ironman race. Reserve far in advance because housing sells out early. In 2024, some of the best hotels in town were blasting music until midnight the night before the race... make sure to have control of your sleeping environment.
Bed 5

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Bath 2

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Sleep 15

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Exceptional(1)

$290.62

/ Nightly
Private Vacation Home

Beautiful Home in Historic Waterfront District, Walk to Downtown!

Cambridge, Maryland, United States

➤ Just 1 block from the water, this Spacious unique Historic Home has been Renovated & Beautifully Furnished for a comfortable stay.brbrThis home has an ideal location in the charming historic district & Ironman Route.br★ Walk to Downtown Restaurants, Pubs, Shops & Cambridge Yacht ClubbrbrHighlights:br★ Large front deck (with a glimpse of the water)br★ Spacious kitchen and dinning area to cook and enjoy family meals br★ Enchanting backyard gardenbr★ Fire Pit for relaxing in the backyard & enjoying smores with family!br★ Pet Friendly
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Sleep 7

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Exceptional(5)

$537.64

/ Nightly
Private Vacation Home

Family-Friendly Cambridge Home w/ Fire Pit!

Cambridge, Maryland, United States

Escape the hustle and bustle of your busy lives and retreat to this 3-bedroom, 2.5-bathroom vacation rental home! Along with a convenient location near the wharf and downtown, this historic American gothic-style home boasts a fully equipped kitchen, a formal dining room, a cozy living room and den with puzzles, and a spacious backyard with corn hole and bocce ball. Explore the downtown attractions, go for a stroll in Long Wharf Park, and visit the Choptank River Lighthouse.brbr-- THE PROPERTY --brbr2,088 Sq Ft | Washer & Dryer | Charcoal Grill | Corn Hole & Bocce Ball | Fenced-In YardbrbrFit for a family vacation on Maryland’s Eastern Shore, this Cambridge getaway is the ideal home-away-from-home!brbrBedroom 1: King Bed, Twin Bed | Bedroom 2: Queen Bed, Twin Bed | Bedroom 3: Full Bed, 2 Twin BedsbrbrKITCHEN: Fully equipped, cooking basics & spices, toaster, drip coffee maker, water cooler, convection oven, dishware & flatware, island w/ seatingbrINDOOR LIVING: 3 Smart TVs, puzzles, dining table, large sectional sofa, ceiling fans, updated interiorbrOUTDOOR LIVING: Backyard, fire pit, Adirondack chairsbrGENERAL: Free WiFi, central A/C, complimentary toiletries, linens & towels, trash bags & paper towels, hangers, hair dryer, keyless entrybrFAQ: Stairs required for access, 2 exterior security cameras (facing out)brPARKING: Street parking (first-come, first-served)brbr-- THE LOCATION --brbrON THE WATER: Sailwinds Park (1.2 miles), Choptank River Lighthouse (1.2 miles), Long Wharf Park (1.2 miles), Cambridge Yacht Basin (1.3 miles), Gerry Boyle Park (2.0 miles), Bill Burton Fishing Pier (3.5 miles), Ferry Point Marina (3.6 miles)brTHINGS TO SEE + DO: Harriet Tubman Museum & Educational Center (0.5 miles), Dorchester Center For The Arts (0.7 miles), Heritage Museum & Gardens of Dorchester (1.6 miles), River Marsh Golf Club (2.4 miles), Dorchester County Visitor Center (5.6 miles), Site of Harriet Tubman Childhood Home (10.0 miles), Blackwater National Wildlife Refuge (10.9 miles)brWINERIES + VINEYARDS: Layton’s Chance Vineyard & Winery (12.8 miles), Far Eastern Shore Winery (16.8 miles), Triple Creek Winery (23.0 miles), St. Michaels Winery (25.8 miles)brLOCAL EATS: Lil' Bitta Bull BBQ (0.4 miles), Jimmie and Sook's (0.6 miles), RAR Brewing (0.6 miles), Ava's Pizzeria & Wine Bar - Cambridge (0.7 miles), Ocean Odyssey Crab House & Restaurant (1.0 miles), Snappers Waterfront Cafe & Tiki Bar (1.0 miles), Porter Soul Food Restaurant (1.1 miles) brSAND + SUN: Ocean City (62.0 miles), Assateague Island National Seashore (63.2 miles)brAIRPORTS: Baltimore/Washington International Thurgood Marshall Airport (79.5 miles), Ronald Reagan Washington National Airport (91.1 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowedbr- No events, parties or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to accessbr- NOTE: Your safety matters. This property features 2 exterior security cameras: 1 camera is located on the front porch facing the porch and front yard, and 1 camera is on the back of the house facing the backyard. The cameras are outward facing and do not look into interior spaces. The cameras are motion activated and record video and sound while guests are in residence
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Sleep 10

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$233.75

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Apartment

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Cambridge, Maryland, United States

Welcome to Pint-Sized on Poplar — a stylishly appointed micro-loft in the heart of downtown Cambridge, MD, sitting directly across the street from the legendary RAR Brewing. This space proves that great things really do come in small packages.brbrEvery inch of this compact one-bedroom has been thoughtfully designed for two. Settle into a plush queen bed backed by a bold tropical mural, brew a morning espresso on the Nespresso Vertuo station (pods included), and take advantage of fast WiFi and a smart HDTV for those rare moments you're not out exploring. The rain head shower and Element Brooklyn bath products make for a spa-worthy start to your day — just don't expect to do any yoga in the bathroom. It's pint-sized, like the name says. But honestly, you're steps from one of the Eastern Shore's best breweries, so you won't be spending much time inside anyway.brbrThe building itself is a beautifully restored historic downtown storefront with classic Victorian-era architectural details, string lights, and all the small-town charm you came here for. You're within walking distance of shops, restaurants, the Choptank River waterfront, and the Harriet Tubman Museum.brbrAmenities:brbr- Queen bed with premium linensbr- Nespresso Vertuo coffee & espresso machine with pod selectionbr- Fast WiFi and smart HDTV with streamingbr- Rain head shower with Element Brooklyn soaps & body washbr- In-unit washer & dryerbr- Kitchenette with marble-style countertopsbr- Dedicated makeup towelbrModern matte black fixtures throughoutbrbrThe Neighborhood:brDowntown Cambridge is in the middle of an exciting revitalization, and this loft puts you at the center of it all. RAR Brewing is literally across the street. The Choptank River waterfront, local galleries, antique shops, and restaurants are all within a short walk. Blackwater National Wildlife Refuge is just 15 minutes away — perfect for kayaking, birding, or a scenic drive.
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Sleep 2

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$109.53

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Private Vacation Home

Fabulous townhome in a safe community in Cambridge

Cambridge, Maryland, United States

Located in Cambridge, enjoy what this 2-Bedroom + Office townhome has to offer. With 1 queen bed and kids bunk beds, guests can relax in the marvelous bedrooms. The property features AC, heating, and an iron for your convenience. brbrEnjoy a sleek kitchen with brand-new appliances and ample counter space. This townhouse is ideal for both everyday living and entertaining. Upstairs, you'll find three bedrooms, including a private primary suite with an en-suite bath. This unit was the model home for the community. You will love it!
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Sleep 5

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Exceptional(57)

$895.7

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Private Vacation Home

Renovated Historic Waterfront Home with Pool, Dock, 200 acres

Cambridge, Maryland, United States

Spocott is a 350-year-old house, newly renovated to provide a unique blend of history, environment, and modern comfort for a large multigenerational family. Located on Gary’s Creek on the Little Choptank River, 5.5 miles west of Cambridge in the historic Neck District of Dorchester County, Spocott House was built in 1663 and has since been owned by the same family. Spocott is the home of a former US Senator and provided inspiration for James Michener in writing Chesapeake. Immerse yourself in history, gaze at wildlife from spacious porches, and engage in a number of indoor and outdoor recreational activities. Sleeping 18 people comfortably, the house with its large waterfront, pool, boat ramp, and dock offers a wonderful opportunity for a private family getaway. Recently renovated, the house has central heating and AC, 7 bedrooms all with a water view and new beds, 3 1/2 baths, and a billiards room. Situated on 200 acres of wildlife management area, the property, bordered by over 1 mile of waterfront, has 5 miles of walking trails, birdwatching stations, ponds, proximity to great biking trails, and scenic views of the Little Choptank River. Consider off-season vacations when up to 10,000 geese inhabit the surrounding waters.
Bed 7

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Sleep 18

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Exceptional(91)

$1233.16

/ Nightly
Private Vacation Home

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge, Maryland, United States

Fishing Cove is a fully-furnished eight-bedroom six-bath private waterfront family-friendly house tucked away in a lush pine forest. Our waterfront vacation home is on a very private cove with 2 acres of waterfront property and a large private dock and 3 boat slips. Easy access by car, or by boat from the Chesapeake Bay.br brDrink your morning coffee on our 12' x 72' deck watching the birds and deer. Fish and crab from our pier. Swim in our pool. Our large welcoming house has everything you need for a relaxed vacation on the Eastern Shore, including accessibility features - electric wheelchair lift, ramps and wide main floor doors. brbrLocated on Fishing Creek off the Little Choptank 9 miles from Cambridge, Maryland, we are near Blackwater National Wildlife Refuge, and our shoreline attracts an amazing variety of waterfowl. We have great bicycling roads: Flat and scenic, so bring your bikes. Bring your canoe and explore the shoreline. The house is wonderful any time of the year!brbrDuring the summer we generally rent by the week only - from Saturday to Saturday, so if the calendar seems confusing, just click on the Saturday you want to begin your stay, and it will automatically offer you a full week. You can always contact the owner if you need different dates that you can't click on.brbrAll new mattresses, new super-fast Fiber Optic WiFi, new geothermal heating and air conditioning system, new paint inside and out, and much more!brbrSorry, we cannot accommodate weddings, wedding receptions or large group events.brNice doggies are considered. Our insurance policy excludes Pitbulls, Rottweilers, Mastifs.
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Bath 6

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Sleep 22

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Exceptional(3)

$262.39

/ Nightly
Apartment

Walk to Park & River: Dog-Friendly Cambridge Gem

Cambridge, Maryland, United States

Half-Mi to Historic Downtown | Covered Porch | Yard Space | Great Fishing AreabrbrWhether you’re here to explore Cambridge’s storied history or bask in the beauty of the waterfront locale, this vacation rental provides a peaceful haven to unwind after your adventures. Check out the shops and museums downtown, visit Harriet Tubman Underground Railroad National Historical Park, or fish on the Choptank River. Later, unwind at this 1-bath studio with a movie marathon. Reserve your stay today!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Studio: 1 queen bed, 1 queen futon brbrOUTDOOR LIVINGbr- Covered porch w/ 2 rocking chairsbr- Partially fenced yard brbrINDOOR LIVINGbr- Flat-screen TVbr- Breakfast barbr- Walk-in showerbr- Board games & booksbrbrKITCHENETTEbr- Refrigerator, toaster oven, microwavebr- Cooking basics, dishware/flatwarebr- Dual coffee maker (drip & pod)brbrGENERAL br- Free WiFi br- Mini-split heating & A/C unit, ceiling fan br- Complimentary toiletries, hair dryerbr- Hangers, linens/towelsbr- Trash bags/paper towels brbrFAQbr- Pet fee (paid pre-trip) br- Homeowner occasionally on-sitebr- 1 Ring doorbell (facing front entry)brbrACCESSIBILITYbr- Single-story studio, exterior staircase to enterbrbrPARKINGbr- Shared driveway (2 vehicles)br- Small boat/trailer parking allowedbrbr-- THE LOCATION --brbr- Walk to Choptank River & Sailwinds Park w/ public boat launch across the street br- Half-mile to Historic Downtown Cambridge: Harriet Tubman Museum and Educational Center, Choptank River Lighthouse, Long Wharf Park, bars, coffee shops, boutiques, restaurantsbr- 12 miles to Harriet Tubman Underground Railroad National Historical Parkbr- 13 miles to Blackwater National Wildlife Refugebr- 61 miles to Ocean City, MD: Ocean City Boardwalk, Jolly Roger Amusement Park, Trimper Rides of Ocean Citybr- 77 miles to Baltimore/Washington International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- Pet friendly w/ $100 fee (+ fees & taxes, dogs only, 1 max) br- No events, parties, or large gatheringsbr- Must be at least 18 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story studio requires an exterior staircase to enter br- The homeowner occasionally occupies an on-site unit with a separate entrance. The homeowner has shared access to the driveway and may be present during your staybr- The rental unit is located in the back of the main property/house and is not visible from the street. Additional directions will be provided after bookingbr- Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed
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Sleep 4

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Exceptional(88)

$1090.28

/ Nightly
Cottage

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Cambridge, Maryland, United States

Cedar Point Cottage | Private Waterfront Retreat | Heated Pool | Dock & Beach | 6.5 Secluded AcresbrbrEscape to Maryland’s beautiful Eastern Shore at Cedar Point Cottage — a beautifully renovated waterfront getaway designed for relaxation, recreation, and unforgettable time together.brbrThis charming private cottage features 3 bedrooms and 2 full bathrooms, offering comfortable space for families or small groups. Inside, you’ll find a brand-new kitchen with updated appliances, welcoming living and dining areas, Smart TV, central A/C, a cozy wood-burning fireplace for cooler evenings, and the convenience of in-home laundry for extended stays.brbrWaterfront Living at Its BestbrbrStep outside and enjoy your own private shoreline and resort-style amenities:brbrHeated waterfront poolbrbrPrivate dock with boat slip (water & electric)brbrKayaks and stand-up paddleboardsbrbrSandy beach areabrbrHammocks for relaxing under the treesbrbrCrab traps for authentic Eastern Shore funbrbrSpacious covered patio with ceiling fan & retractable screensbrbrOutdoor grill for dining al frescobrbrFire pit with firewood providedbrbrSpend your mornings kayaking at sunrise, afternoons lounging by the pool, and evenings gathered around the fire pit under the stars. Whether you’re crabbing off the dock, boating from your private slip, or simply unwinding in a hammock with water views, Cedar Point Cottage offers peaceful privacy with modern comfort.brbrPerfect for families, couples, or small groups seeking space, serenity, and true waterfront living on the Eastern Shore.brbrNo pets.
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Sleep 9

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Exceptional(15)

$856.83

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Private Vacation Home

House close to Great Marsh Park and Downtown

Two story Three bedroom house on tree line street half block from Great Marsh Park and Choptank River walking distance to downtown Cambridge. Screen front porch fenced yard, deck off of kitchenbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbrbr.
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Sleep 6

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Exceptional(2)

$359.0

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Private Vacation Home

Beautiful Peaceful Home

Cambridge, Maryland, United States

Look no further than this listing that offers a modern and well-built home in a safe and monitored neighborhood. The house is conveniently located near all the attractions and amenities that Cambridge has to offer, making it easy to explore the local shops and restaurants, take a walk along the scenic waterfront, or simply relax and enjoy the peaceful surroundings. The hosts take pride in providing guests with a comfortable stay, and are always available to answer questions. Rental options are available from 3 months to a year lease. No short term rentals.
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Home Rent a place that suits your needs

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Home Most popular vacation rentals in Cambridge

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Exceptional(2)

$486.47

/ Nightly
Private vacation home

Attractive Waterfront Home over looking Choptank River. Sleeps 5

Cambridge, Maryland, United States

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Sleep 5

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Exceptional(2)

$375.73

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Private vacation home

High Water Guest House

Cambridge, Maryland, United States

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Sleep 6

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Exceptional(2)

$376.30

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Private vacation home

Escape with family or friends to this peaceful, 4-bedroom retreat on the water

Cambridge, Maryland, United States

Bed 4

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Sleep 8

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Exceptional(2)

$397.50

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Private vacation home

Peaceful Cambridge Home on Jenkins Creek

Cambridge, Maryland, United States

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Bath 2

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Sleep 6

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Exceptional(2)

$481.69

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Condo

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Cambridge, Maryland, United States

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Sleep 6

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Exceptional(2)

$483.08

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Private vacation home

Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge

Cambridge, Maryland, United States

Bed 5

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Bath 2

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Sleep 15

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Exceptional(2)

$520.83

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Private vacation home

Charming, waterfront 3-bedroom house in lovely Cambridge with AC, WiFi

Cambridge, Maryland, United States

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Bath 3

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Sleep 10

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Exceptional(2)

$537.64

/ Nightly
Private vacation home

Family-Friendly Cambridge Home w/ Fire Pit!

Cambridge, Maryland, United States

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Bath 2

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Sleep 10

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Exceptional(2)

$530.57

/ Nightly
Private vacation home

New, Intown Waterfront Townhome wPool & Location!

Cambridge, Maryland, United States

Bed 3

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Bath 2

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Sleep 8

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Exceptional(2)

$371.00

/ Nightly
Cottage

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge, Maryland, United States

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Bath 1

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Sleep 6

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Most Popular Cities in Maryland