Dorchester Area, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Dorchester Area, Maryland on RentalSaver.com!

Dorchester Area Rentals

From $885 per night (USD)
VRBO
Beautiful Bayside Villa on Chesapeake
Bedrooms:
5
Bathrooms:
6
Sleeps:
20
Welcome to the beautiful villa on Chesapeake bay. Your dream vacation awaits with something for the whole family! Locate ...
From $885 per night (USD)
VRBO
From $269 per night (USD)
Expedia
Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our charming 3-bedroom Midcentury modern home in Cambridge! This stunning home boasts a retro vibe with uniqu ...
From $269 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Waterfront property with private boat ramp and new dock!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private Boat Ramp and Large New Pier on your property! Launch your own boat from the private boat ramp or enjoy our wa ...
From $254 per night (USD)
VRBO
From $375 per night (USD)
Expedia
High Water Guest House<br>
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of h ...
From $375 per night (USD)
Expedia
From $165 per night (USD)
VRBO
Waterfront Getaway for Two
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Swan Cove Manor is a 27 acre private 5 house estate with 3 waterfront homes and 2 non-waterfront homes. This room is a ...
From $165 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Enjoy historic Cambridge all year at this fully stocked and freshly renovated 2 bedroom, 2.5 bath townhouse across the s ...
From $284 per night (USD)
Expedia
From $207 per night (USD)
VRBO
The Blackwater refuge country house on a quiet 12 acres
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Newly renovated house located in lower Dorchester County with fire pit and gazebo for entertaining family and friends. P ...
From $207 per night (USD)
VRBO
From $639 per night (USD)
Expedia
New Island Home on the Chesapeake Bay Sunsets
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
This newly built home on Hoopers Island offers you, your family, and friends a cozy, quiet, and peaceful retreat from th ...
From $639 per night (USD)
Expedia
From $1182 per night (USD)
VRBO
Scenic and private waterfront eastern shore home.
Bedrooms:
3
Bathrooms:
5
Sleeps:
18
Welcome to "The Cove at Cambridge" in Cambridge, Maryland. It is located on a private 38-acre farm with over 1000 ft of ...
From $1182 per night (USD)
VRBO
$Farmhouse Charm Woolford Studio Apt. w/ Amazing Eastern Shore Sunrise & Sunsets\n$
Click For Pricing
Expedia
Farmhouse Charm Woolford Studio Apt. w/ Amazing Eastern Shore Sunrise & Sunsets\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy this beautiful Brand new Completely refinished loft studio above two car garage,, just behind the Main Cottage. S ...
Click For Pricing
Expedia
$Charming 4 bedroom in Historic Cambridge\n\n$
From $527 per night (USD)
VRBO
Charming 4 bedroom in Historic Cambridge\n\n
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Enjoy the old world charm of this home, built in 1894 in the historic district of the picturesque and diverse town of Ca ...
From $527 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to this fully renovated historic condo nestled in the heart of downtown Cambridge, Maryland, with its fabulous d ...
From $219 per night (USD)
Expedia
From $512 per night (USD)
VRBO
365-degree waterfront views. Quiet property bordering Blackwater River Refuge.
Bedrooms:
4
Bathrooms:
8
Sleeps:
13
Get away from the city and forget your worries in this spacious and serene lodge that borders Blackwater National Wildli ...
From $512 per night (USD)
VRBO
From $587 per night (USD)
Expedia
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Enjoy this large peaceful Waterfront cabin-style home with your whole group! This beautifully updated home is super spac ...
From $587 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Waterviews, Comfort & Convenience!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Looking for some rest or relief…or perhaps just a little fun? This home is just steps away from the Cambridge Yacht Basi ...
From $383 per night (USD)
VRBO
From $547 per night (USD)
Expedia
About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger!
Bedrooms:
2
Bathrooms:
5
Sleeps:
15
About Time: A Tranquil Eastern Shore Retreat for Families, Friends, and Multi-Generational Vacations: Welcome to About T ...
From $547 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Conductor's Rest, a fully renovated 2-bedroom historic condo nestled in the heart of downtown Cambridge, Mary ...
From $288 per night (USD)
VRBO
From $218 per night (USD)
VRBO
Nanticoke river front Studio!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Relax in our cozy river front apartment suite. The apartment is located in our stand alone garage next to our primary re ...
From $218 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Hambrooks Home with Hottub/ Mid Term stays welcomed!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to my home of 2 beds, 2 baths, a large office so you can keep your nose to the grindstone if desired, and plenty ...
From $177 per night (USD)
VRBO
From $493 per night (USD)
VRBO
Waterfront Cambridge Home: Pool & Dock!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Find your slice of paradise at ‘Hudson Creek Retreat,’ a 4-bed, 4-bath Cambridge vacation rental. This family home offer ...
From $493 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Fabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Looking for an Eastern Shore beachfront retreat that's perfect for a romantic long weekend, a family vacation with the k ...
From $409 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Cambridge is waiting for you at this enchanting 4-bedroom house. Step inside and be greeted by the amazing decor that ex ...
From $223 per night (USD)
Expedia
From $397 per night (USD)
VRBO
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to Choptank Riverside Retreat, your peaceful escape in historic Cambridge, MD. Designed for rest and rejuvenatio ...
From $397 per night (USD)
VRBO
$The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge$
From $277 per night (USD)
Expedia
The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to The Drinking Gourd...a freshly renovated 2-bedroom penthouse in the heart of the historic downtown district o ...
From $277 per night (USD)
Expedia
From $1086 per night (USD)
VRBO
Ironman & Eagleman - 4-bedroom house in charming Cambridge.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This 4-bedroom house in Cambridge is perfect for your Eastern Shore experience. With 2 queen beds and 4 twin beds, guest ...
From $1086 per night (USD)
VRBO
From $1007 per night (USD)
Expedia
Gorgeous retreat across from yacht club, the Choptank, and IronMan finish line!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The perfect location for an easy getaway in any season. The home is across the street from the IRONMAN Maryland finish l ...
From $1007 per night (USD)
Expedia
$\Belle Aire Landing\ a Large Beautiful Waterfront Estate! Under New Management!$
From $2014 per night (USD)
VRBO
\"Belle Aire Landing\" a Large Beautiful Waterfront Estate! Under New Management!
Bedrooms:
6
Bathrooms:
9
Sleeps:
22
*Under New Management for 2025!* When thinking about an amazing vacation, the words that come to mind should be like 'A ...
From $2014 per night (USD)
VRBO
From $174 per night (USD)
Expedia
Sailwinds Loft at Cambridge Creek
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Waterview second story loft apartment in downtown Cambridge, MD with private entrance and secure bike storage! Located j ...
From $174 per night (USD)
Expedia
From $894 per night (USD)
VRBO
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,15%off 7day stay
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Welcome to Juniper Cove! Large luxury waterfront home on 15 private acres, with a large in-ground salt water pool in Cam ...
From $894 per night (USD)
VRBO
From $286 per night (USD)
Expedia
Escape with family or friends to this peaceful, 4-bedroom retreat on the water
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Escape with family or friends to this peaceful, 4-bedroom retreat on the waterfront. With breaktaking views of the river ...
From $286 per night (USD)
Expedia
$\Endless Summer\ Waterfront on the Chesapeake Bay!$
From $654 per night (USD)
VRBO
\"Endless Summer\" Waterfront on the Chesapeake Bay!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
A private waterfront Oasis! This exceptional 4 bedroom, 3 bathroom Rural waterfront Eastern Shore home sits on over 6 ac ...
From $654 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge
Bedrooms:
2
Bathrooms:
5
Sleeps:
15
Escape to this stunningly renovated 5-bed waterfront home on Hudson Creek in Cambridge, MD. Perfect for both luxury seek ...
From $455 per night (USD)
Expedia
From $1257 per night (USD)
VRBO
Short drive to Downtown Cambridge | Private Dock | Guest House
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
Bucolic and Serene NEW POOL COMING SOON! This charming 6BR, 3BA Victorian waterfront vacation home complimented by a 1B ...
From $1257 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Charming, waterfront 3-bedroom house in lovely Cambridge with AC, WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Get ready to relax by the water in this 3-bedroom house in Cambridge. This charming waterfront property features 2 king ...
From $481 per night (USD)
Expedia
From $322 per night (USD)
VRBO
Amazing views waterfront 3-bedroom home in Madison
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Bring the whole family to this peaceful place to stay. Located on the water at Madison Bay, just south of Cambridge. The ...
From $322 per night (USD)
VRBO
From $325 per night (USD)
VRBO
Hoopers Island Victorian with 360 Water Views - experienced host
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
New to VRBO so no reviews, but a quick google will show you 5* reviews raving about the place. This one pretty much sums ...
From $325 per night (USD)
VRBO
From $160 per night (USD)
VRBO
Cambridge Apt in Walkable Neighborhood
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Waterfront Setting | Close to Local Eats Explore the quiet side of the Chesapeake Bay with your closest travel buddy at ...
From $160 per night (USD)
VRBO
From $351 per night (USD)
VRBO
Walk to Dtwn: Waterfront Eastern Shore Townhome!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Game Room | Scenic Waterfront Deck | Community Pool | Pet Friendly w/ Fee | EV Charger Experience life in the heart of ...
From $351 per night (USD)
VRBO
From $738 per night (USD)
VRBO
New! Chesapeake Bay Retreat!
Bedrooms:
3
Bathrooms:
6
Sleeps:
16
Escape to this lovely 6-bedroom house and guest house on the Chesapeake Bay for a relaxing getaway. Amazing Freightliner ...
From $738 per night (USD)
VRBO
$Lovely 3-bedroom house AC WiFi in the charming Cambridge,\nGreat Location!!!!$
From $229 per night (USD)
Expedia
Lovely 3-bedroom house AC WiFi in the charming Cambridge,\nGreat Location!!!!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Discover this wonderful 3-bedroom gem in Cambridge. Great location!!! This awesome house features 1 bunk bed, 1 twin bed ...
From $229 per night (USD)
Expedia
$Aurora Blue - A Stylish Experience \n$
From $270 per night (USD)
VRBO
Aurora Blue - A Stylish Experience \n
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Stylish experience at the centrally located retreat. New owners purchased East and renovated the entire home both inside ...
From $270 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Chesapeake Sunset Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
About this space Only sunsets and stars. No neighbor. Surrounded on three sides by water. Totally quiet. Modern but peac ...
From $452 per night (USD)
Expedia
From $1258 per night (USD)
VRBO
Spacious 7-bedroom property with guest house, Wifi, AC in lovely Cambridge
Bedrooms:
4
Bathrooms:
7
Sleeps:
6
Take it all in and relax at this beatiful Cambridge waterfront getaway on nearly five acres. It boasts a guest house wit ...
From $1258 per night (USD)
VRBO
From $252 per night (USD)
VRBO
About Time-Bunkhouse Only
Bedrooms:
1
Bathrooms:
2
Sleeps:
10
Experience Taylors Island like a local in this 2-bedroom house. The bedrooms feature 1 queen bed and 1 twin bed, perfect ...
From $252 per night (USD)
VRBO
From $275 per night (USD)
VRBO
About Time-Main House
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Access to one of two full houses, see our other listing to book both houses. Perfectly set up for a multi-generational, ...
From $275 per night (USD)
VRBO
From $897 per night (USD)
VRBO
Waterfront Retreat w Heated Salt Water Pool: Private Pier w Boat Docking
Bedrooms:
2
Bathrooms:
4
Sleeps:
15
Welcome to your perfect family getaway on Maryland’s Eastern Shore! Set on 4 peaceful acres along the river, our home is ...
From $897 per night (USD)
VRBO
From $576 per night (USD)
VRBO
Hoopers Island Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Hoopers Island is where coastal comfort meets waterfront luxury! This newly renovated 3-bedroom, 5 bed, 2.5-bathroom wat ...
From $576 per night (USD)
VRBO
From $360 per night (USD)
Expedia
3-bedroom waterfront retreat in Secretary, Maryland
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your peaceful retreat in the heart of Secretary. This charming 3-bedroom home comfortably sleeps up to 6 gues ...
From $360 per night (USD)
Expedia
$Waterfront Historic \Old Bank\ on Hoopers Island$
From $328 per night (USD)
VRBO
Waterfront Historic \"Old Bank\" on Hoopers Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
A step back in time with all the modern amenities you are accustomed to. Fabulous sunset views out to Baron Island and ...
From $328 per night (USD)
VRBO
From $180 per night (USD)
VRBO
Walk to Park & River: Dog-Friendly Cambridge Gem
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Half-Mi to Historic Downtown | Covered Porch | Yard Space | Great Fishing Area Whether you’re here to explore Cambridge ...
From $180 per night (USD)
VRBO
From $216 per night (USD)
VRBO
Walkable Condo w/ Drawbridge Views in Cambridge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Community Pool | Walk to Happy Hour at Portside | River-View Balcony Dive into waterfront serenity at this Cambridge va ...
From $216 per night (USD)
VRBO
From $110 per night (USD)
Expedia
Fabulous townhome in a safe community in Cambridge
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Located in Cambridge, enjoy what this 2-Bedroom + Office townhome has to offer. With 1 queen bed and kids bunk beds, gue ...
From $110 per night (USD)
Expedia
From $992 per night (USD)
VRBO
NEW! Cattail Cove: Waterfront Retreat w/Guest House, Hot Tub, Pool,Fire Pit,Dock
Bedrooms:
3
Bathrooms:
6
Sleeps:
13
Welcome to Cattail Cove, the perfect riverside escape! We want you to enjoy our gorgeous waterfront oasis where you have ...
From $992 per night (USD)
VRBO
From $127 per night (USD)
Expedia
Station House East: Upscale Loft in the Historic District Cambridge, MD
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step into style and comfort in this beautifully appointed 1-bedroom, 1.5-bath condo located in the iconic Four Corners ...
From $127 per night (USD)
Expedia
From $374 per night (USD)
VRBO
< 1 Mi to Dtwn: Waterfront Townhome in Cambridge!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Private Deck w/ Views | 1,800 Sq Ft | Gated Community Your tranquil escape awaits at this modern and airy vacation rent ...
From $374 per night (USD)
VRBO
From $1641 per night (USD)
Expedia
250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!
Bedrooms:
10
Bathrooms:
12
Sleeps:
40
Ransome’s Chesapeake Retreats, LLC is in the business of bringing families, friends, loved ones together from around the ...
From $1641 per night (USD)
Expedia

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Dorchester Area Rentals

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Results: 156 Rentals