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 $1291 per night (USD)
VRBO
Private 2 Acre Waterfront Family Retreat with Pool & Pier
Bedrooms:
6
Bathrooms:
8
Sleeps:
22
Fishing Cove is a fully-furnished eight-bedroom six-bath private waterfront family-friendly house tucked away in a lush ...
From $1291 per night (USD)
VRBO
From $915 per night (USD)
VRBO
Renovated Historic Waterfront Home with Pool, Dock, 200 acres
Bedrooms:
4
Bathrooms:
7
Sleeps:
18
Spocott is a 350-year-old house, newly renovated to provide a unique blend of history, environment, and modern comfort f ...
From $915 per night (USD)
VRBO
From $399 per night (USD)
VRBO
Spacious, pet-friendly 3-bedroom home
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape to this updated, single-level home with 3 bedrooms, a separate office (with doors), high-speed wifi, a large FENC ...
From $399 per night (USD)
VRBO
From $671 per night (USD)
Expedia
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Bedrooms:
2
Bathrooms:
4
Sleeps:
15
This 4 bedroom 2 bath home is perfectly situated on a picturesque peninsula on Hudson Creek. There is a beautiful water ...
From $671 per night (USD)
Expedia
From $638 per night (USD)
VRBO
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Come get away to a private oasis on the Warwick River, 10 minutes from the Hyatt and Historic Cambridge. It's as quiet a ...
From $638 per night (USD)
VRBO
From $862 per night (USD)
VRBO
Beautiful, Waterfront Home -- Perfect for Large Families and Groups!
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Hudson Creek Beautiful Private Estate has it all and is a Perfect Get Away! Think of it as a Country Home on the Water - ...
From $862 per night (USD)
VRBO
From $530 per night (USD)
VRBO
Beautiful Colonial Home on the Choptank River
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to this newly updated 4-bedroom, 2-bath colonial home for a fun-filled retreat on the Cambridge coast! Offering k ...
From $530 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Waterfront Getaway with Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bicyclist's and outdoorsman's dream! Neat little rancher on two waterfront acres just 4 miles from Blackwater Wildlife R ...
From $251 per night (USD)
Expedia
From $923 per night (USD)
VRBO
Waterfront Nature/Outdoor Lovers Secluded Estate
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Thunderstick Lodge is 158-acre outdoor lovers paradise. This late 1800s built estate was totally remodeled in 2020. Eigh ...
From $923 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Single family home with screened porch.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Water view cozy remolded 118 year old home with a large, screened porch, gas log fireplace for winter stays, Blackwater ...
From $348 per night (USD)
Expedia
From $700 per night (USD)
VRBO
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Beautifully appointed 19th century farmhouse situated on 23 acres of pristine beauty with pool and 2,000 feet of unspoil ...
From $700 per night (USD)
VRBO
From $1101 per night (USD)
VRBO
A Vacation Away From It All-Family And Pet Friendly
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Built in 1990, this exceptional post and beam Lodge offers over 4,700 square feet with 5 bedrooms and 5 baths. Random-wi ...
From $1101 per night (USD)
VRBO
From $459 per night (USD)
VRBO
Sunset Breezes - quiet waterfront retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. G ...
From $459 per night (USD)
VRBO
From $609 per night (USD)
VRBO
Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Create unforgettable memories by reserving your riverside retreat today! The primary bedroom features a luxurious king ...
From $609 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Cottage on Cabin Creek
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The cottage is the perfect place for a couple's get away. The views of Cabin Creek are stunning. You will enjoy beautifu ...
From $299 per night (USD)
VRBO
From $337 per night (USD)
VRBO
The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Better pricing on other sites, Please look there. 'The Cottage' at Heron Cove is a cozy retreat situated on a scenic p ...
From $337 per night (USD)
VRBO
From $549 per night (USD)
VRBO
BayDreams - IronMan/Eagleman Retreat on the bay
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Heavenly sunsets will dazzle you at our Chesapeake Bay vacation home. Whether you are fishing, crabbing, paddle boarding ...
From $549 per night (USD)
VRBO
From $1688 per night (USD)
VRBO
Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Weddings are allowed at Swan Cove Manor, however in most cases the whole five house estate must be rented out. Further d ...
From $1688 per night (USD)
VRBO
From $8126 per night (USD)
VRBO
Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate
Bedrooms:
15
Bathrooms:
20
Sleeps:
70
***Waterfronts homes with pools are booked until September 13, 2020. We are also taking reservations for 2021*** This es ...
From $8126 per night (USD)
VRBO
From $1690 per night (USD)
VRBO
Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 14
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
The Spinnaker at Swan Cove has a great location on 6 private waterfront acres and awaits your next family vacation or ge ...
From $1690 per night (USD)
VRBO
From $710 per night (USD)
VRBO
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
We would like to welcome you to our charming getaway. This is the ideal spot for families, friends, or business retreats ...
From $710 per night (USD)
VRBO
From $258 per night (USD)
Expedia
BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
BRAND NEW GAZEBO!!! WITH A TABLE THAT SEATS 10 AND ADDITIONAL SEATS AVAILABLE!! GREAT PLACE TO EAT N BE AWAY FROM BUGS ...
From $258 per night (USD)
Expedia
From $1826 per night (USD)
VRBO
Waterfront Family Retreat with Pool on 7+ acres!
Bedrooms:
5
Bathrooms:
10
Sleeps:
24
Looking for a place to really enjoy nature, boating, fishing, swimming, family games, campfires and more? Bring your boa ...
From $1826 per night (USD)
VRBO
From $869 per night (USD)
Expedia
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
This charming century old Eastern Shore farmhouse is situated on Brooks Creek in the heart of the Chesapeake Bay. It is ...
From $869 per night (USD)
Expedia
From $557 per night (USD)
VRBO
Relaxing getaway at Outrigger w/ plenty of space sleeping up to 21
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Nestled on 22 acres the Outrigger is one of 5 homes on the property. Very private, ample parking and a fully stocked kit ...
From $557 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Riverside Lodge Bed & Breakfast on the Honga River UNIT B
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
NEWLY RENOVATED ROOMS! A historic Lodge on the Honga River and the Chesapeake Bay, Riverside Lodge offers overnight acco ...
From $325 per night (USD)
Expedia
From $1688 per night (USD)
VRBO
Waterfront Home with Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 20
Bedrooms:
3
Bathrooms:
5
Sleeps:
18
The Mariner on Swan Cove has a very private location and awaits your next family vacation getaway. It is one of 5 homes ...
From $1688 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
NEWLY RENOVATED ROOMS! A historic Lodge on the Honga River and the Chesapeake Bay, Riverside Lodge offers overnight acco ...
From $328 per night (USD)
Expedia
Click For Pricing
VRBO
Riverside Lodge Bed & Breakfast on the Honga River UNIT D
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
NEWLY RENOVATED ROOMS! A historic Lodge on the Honga River and the Chesapeake Bay, Riverside Lodge offers overnight acco ...
Click For Pricing
VRBO
From $328 per night (USD)
Expedia
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
NEWLY RENOVATED ROOMS! A historic Lodge on the Honga River and the Chesapeake Bay, Riverside Lodge offers overnight acco ...
From $328 per night (USD)
Expedia
From $490 per night (USD)
VRBO
Historic Hoopersville Getaway on Chesapeake Bay!
Bedrooms:
2
Bathrooms:
7
Sleeps:
15
The historic Queen Anne Victorian vacation rental home is the perfect getaway for friends and family. With 7 bedrooms, 2 ...
From $490 per night (USD)
VRBO
From $1356 per night (USD)
Expedia
Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Beautiful Private Retreat with Pool located on Covey Creek The Bird's Nest on Covey Creek is a comfortable and well-app ...
From $1356 per night (USD)
Expedia
From $478 per night (USD)
VRBO
Family-Friendly Cambridge Home w/ Fire Pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Escape the hustle and bustle of your busy lives and retreat to this 3-bedroom, 2.5-bathroom vacation rental home! Along ...
From $478 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Riverside Lodge Bed & Breakfast on the Honga River UNIT A
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
NEWLY RENOVATED ROOMS! A historic Lodge on the Honga River and the Chesapeake Bay, Riverside Lodge offers overnight acc ...
From $328 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Quarterdeck cottage at Swan Cove Manor - A cozy stay for up to 4 people
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled on 22 acres, the Quarterdeck at Swan Cove Manor is one of five homes on the property. Very private with private ...
From $376 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our charming 2-bedroom farm stay in the heart of Fishing Creek! Nestled in a picturesque setting, this cozy a ...
From $265 per night (USD)
Expedia
From $722 per night (USD)
VRBO
Bayfront Gem w/ Amazing Water Views + Pond!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Whether you’re in town for leisure or business, this vacation rental is the perfect setting for your next retreat to Mar ...
From $722 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Delightful waterfront vacation cottage. Pet friendly with fee. Sleeps 4 people and has a pack and play and high chair ...
From $347 per night (USD)
Expedia
From $680 per night (USD)
VRBO
The Water's Edge Rental Cambridge, Md - sleeps 10, 4 bedrooms
Bedrooms:
0
Bathrooms:
4
Sleeps:
10
Waterfront Home w/ Private 150’ Pier | Kayaks | Paddleboard | Bikes | Yard Games | Family-Friendly This waterfront vaca ...
From $680 per night (USD)
VRBO
From $643 per night (USD)
Expedia
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
WATERFRONT! HOT TUB! KAYAKS! Relax with the entire family at this peaceful 3 bedroom private waterfront cottage on a qui ...
From $643 per night (USD)
Expedia
From $1843 per night (USD)
VRBO
Eagles Nest. Discover Tranquility, Privacy, Excellence, and so much more.
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
From our first steps on this property over 35 years ago my wife and I visualized the delicate balance between nature and ...
From $1843 per night (USD)
VRBO
From $500 per night (USD)
VRBO
Attractive Waterfront Home over looking Choptank River. Sleeps 5
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
This waterfront home has a open floor plan for entertaining and comfortable living. The view of the river is fully visi ...
From $500 per night (USD)
VRBO
From $1686 per night (USD)
VRBO
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Bedrooms:
5
Bathrooms:
5
Sleeps:
18
Choptank oasis offers the perfect Eastern Shore experience: 200' pier great for crabbing and fishing, river kayaking/ca ...
From $1686 per night (USD)
VRBO
From $828 per night (USD)
VRBO
Peaceful family get away with in ground pool close to town
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Pool is open April through September! Only 4 miles from town, come and relax in this newly renovated 2750 sq ft waterf ...
From $828 per night (USD)
VRBO
$Waterfront Historic \Old Bank\ on Hoopers Island$
From $342 per night (USD)
VRBO
Waterfront Historic \"Old Bank\" on Hoopers Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
In this quaint town of Fishing Creek is located our lovely three-bedroom getaway. Nestled just a 24-minute drive from th ...
From $342 per night (USD)
VRBO
From $310 per night (USD)
VRBO
Sunrise Waterfront Cottage in Beautiful Hoopers Island
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Enjoy the quiet and serenity of Hoopers Island from our cozy waterfront cottage. Take a break from the hustle and bustl ...
From $310 per night (USD)
VRBO
From $420 per night (USD)
VRBO
Cottage on the Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
3 Bedroom, 2 bath house on the Bay side of Hoopers Island on the Chesapeake Bay. Large yard and screened in deck on the ...
From $420 per night (USD)
VRBO
From $1196 per night (USD)
Expedia
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
5+ acres, private pool, wide water, sandy beach, dock, boats, firepit & bikes Beautiful, newer custom 3-story home w/ w ...
From $1196 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Family and Pet-Friendly, Waterfront with Pier
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
There are two houses on the property. In June of 2015 we completed a full and total re-build of the carriage house and ...
From $339 per night (USD)
VRBO
From $1907 per night (USD)
VRBO
250 ACRE RETREAT CHESAPEAKE BAY VACATION/REUNION/WEDDING 12 BEDROOMS, SLEEPS 40
Bedrooms:
8
Bathrooms:
12
Sleeps:
40
Ransome’s Chesapeake Retreats, LLC is in the business of bringing families, friends, loved ones together from around th ...
From $1907 per night (USD)
VRBO
Click For Pricing
VRBO
Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Waterfront Retreat on 4 Private Acres | Pool, Dock, Kayaks & Game Barn Welcome to your private Eastern Shore escape—whe ...
Click For Pricing
VRBO
From $2125 per night (USD)
Expedia
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Bedrooms:
5
Bathrooms:
7
Sleeps:
20
Treat yourself to this unique waterfront retreat where you’ll enjoy stunning ocean liner views of the Choptank River fro ...
From $2125 per night (USD)
Expedia
From $308 per night (USD)
VRBO
Cheerful three-bedroom Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Introducing River Light Cottage, the perfect escape in historic Cambridge, Maryland! A short walk from downtown shops an ...
From $308 per night (USD)
VRBO
From $1378 per night (USD)
Expedia
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
Bedrooms:
5
Bathrooms:
8
Sleeps:
16
Looking for that “shore” lifestyle? This 3,800 square foot, 8-bedroom, 5-bathroom waterfront estate on Brooks Creek off ...
From $1378 per night (USD)
Expedia
From $829 per night (USD)
VRBO
Private 9 acre Family Retreat on the Chesapeake Bay
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
This beautiful large home consists of 5 bedrooms, 4 bathrooms with stunning views of the Chesapeake. The home offers a l ...
From $829 per night (USD)
VRBO
From $415 per night (USD)
Expedia
New, Intown Waterfront Townhome wPool & Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Perfect, large property for an extended, family or group stay at this superb Chesapeake retreat -- part of a g ...
From $415 per night (USD)
Expedia
From $2010 per night (USD)
VRBO
Remarkable waterfront property on 270 acres
Bedrooms:
6
Bathrooms:
5
Sleeps:
15
Located on the Little Choptank River, Cherry Point Farm is a 280-acre historic sporting estate with over 25,000 feet of ...
From $2010 per night (USD)
VRBO
From $1494 per night (USD)
VRBO
Waterfront retreat, beautiful views!
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
Beautiful, sun-filled, waterfront home where the Choptank meets the Chesapeake Bay. Water views from nearly every window ...
From $1494 per night (USD)
VRBO
From $545 per night (USD)
VRBO
Waterfront Retreat < 4 Mi to Dtwn Cambridge!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Experience a peaceful waterfront retreat on Maryland’s eastern shore at this stunning Cambridge vacation rental! Complet ...
From $545 per night (USD)
VRBO
From $333 per night (USD)
Expedia
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Relax and unwind at our 2 acre waterfront cottage. Enjoy the private dock, kayaks, fire pit, front porch, or back deck! ...
From $333 per night (USD)
Expedia
From $1899 per night (USD)
VRBO
Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub
Bedrooms:
6
Bathrooms:
8
Sleeps:
17
Cozy Yet Spacious Waterfront Getaway! This 8BR, 5 BA, 2 HBA property is what you are looking for! Your dream vacation a ...
From $1899 per night (USD)
VRBO
From $330 per night (USD)
VRBO
Casual Bungalow close to Choptank River, sleeps 5
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A newly renovated pristine bungalow close to downtown Cambridge, MD. We are conveniently located near St. Michael, East ...
From $330 per night (USD)
VRBO
From $394 per night (USD)
VRBO
A little slice of heaven on the Choptank River.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A perfect getaway on our waterfront property .You will have your own private beach. You can enjoy crabbing ,fishing , ka ...
From $394 per night (USD)
VRBO
From $473 per night (USD)
Expedia
New Waterfront! Drop Anchor on Brannocks Bay. An Amazing waterfront retreat!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Take it easy at this unique and tranquil getaway located on the Choptank River with oceanliner views of the Chesapeake B ...
From $473 per night (USD)
Expedia
From $430 per night (USD)
VRBO
New listing! Riverside Retreat on the Choptank River
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your dream vacation in the historic city of Cambridge, Maryland! This charming well appointed Riverview renta ...
From $430 per night (USD)
VRBO
From $817 per night (USD)
Expedia
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Bright, rustic, waterfront farmhouse retreat resting on over 9 acres. The water views can be enjoyed almost anywhere fro ...
From $817 per night (USD)
Expedia
From $807 per night (USD)
VRBO
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Bedrooms:
4
Bathrooms:
6
Sleeps:
18
Welcome to The Blue Heron, named for "Henry", the Heron that visits daily. Spacious areas for large groups to gather a ...
From $807 per night (USD)
VRBO
From $908 per night (USD)
Expedia
Goose landing Waterfront Delight! Lee Creek Farm is a vacation oasis!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Goose Landing! Bring the entire family! Inground Pool, Kayaks, canoes, fire pit, ping pong all in a country setting! - T ...
From $908 per night (USD)
Expedia
From $1364 per night (USD)
VRBO
Waterfront Home w/ Stunning Views, Deepwater Dock, Pool, HotTub, Kayaks & More
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Escape to your private waterfront retreat in this 4,500 sq. ft. luxury home just off the Choptank River. Floor-to-ceilin ...
From $1364 per night (USD)
VRBO
From $380 per night (USD)
Expedia
Luxury on the river, steps to downtown &boat ramp!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Beautifully crafted 1915 Sailmakers home nestled perfectly off the choptank harbor. Newly renovated with stunning appoin ...
From $380 per night (USD)
Expedia
From $1412 per night (USD)
VRBO
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Bedrooms:
5
Bathrooms:
7
Sleeps:
27
Discover the epitome of luxury at this 7-bedroom, 5.5-bathroom vacation rental in Cambridge. Boasting over 10,000 square ...
From $1412 per night (USD)
VRBO
From $347 per night (USD)
VRBO
The Crabby Little Oyster Cottage in Cambridge MD
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Crabby Little Oyster Cottage offers incomparable peace and quiet and convenience. This 3 bedroom, 1.5 bath home slee ...
From $347 per night (USD)
VRBO
From $1201 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 $1201 per night (USD)
VRBO
From $323 per night (USD)
VRBO
Waterfront Cottage at Hudson Creek - Cozy Year-Round Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to The Cottage at Hudson Creek — a cozy waterfront retreat with its own private boat ramp and a large, newly bui ...
From $323 per night (USD)
VRBO
From $549 per night (USD)
VRBO
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 $549 per night (USD)
VRBO
From $316 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 $316 per night (USD)
VRBO
From $392 per night (USD)
VRBO
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 $392 per night (USD)
VRBO
From $255 per night (USD)
Expedia
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 $255 per night (USD)
Expedia
From $679 per night (USD)
VRBO
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 $679 per night (USD)
VRBO
From $364 per night (USD)
Expedia
Beautiful Home in Historic Waterfront District, Walk to Downtown!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
➤ Just 1 block from the water, this Spacious unique Historic Home has been Renovated & Beautifully Furnished for a comfo ...
From $364 per night (USD)
Expedia
From $1388 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 $1388 per night (USD)
VRBO
From $590 per night (USD)
VRBO
Charming 4 bedroom in Historic Cambridge
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 $590 per night (USD)
VRBO
From $681 per night (USD)
VRBO
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 $681 per night (USD)
VRBO
From $741 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 $741 per night (USD)
Expedia
From $662 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 $662 per night (USD)
VRBO
From $475 per night (USD)
Expedia
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 $475 per night (USD)
Expedia
From $285 per night (USD)
VRBO
La Casa Azul . with Wi-Fi, 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 $285 per night (USD)
VRBO
From $529 per night (USD)
Expedia
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Welcome to Choptank Riverside Retreat, your peaceful escape in historic Cambridge, MD. Designed for rest and rejuvenatio ...
From $529 per night (USD)
Expedia
From $368 per night (USD)
VRBO
The Drinking Gourd: Stunning 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 $368 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $1143 per night (USD)
VRBO
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 $1143 per night (USD)
VRBO
$Chesapeake Bay Large Beautiful Waterfront Estate! \Belle Aire Landing\$
From $2061 per night (USD)
Expedia
Chesapeake Bay Large Beautiful Waterfront Estate! \"Belle Aire Landing\"
Bedrooms:
6
Bathrooms:
9
Sleeps:
22
When thinking about an amazing vacation, the words that come to mind should be like 'Amazing', 'Unforgettable', and 'spe ...
From $2061 per night (USD)
Expedia
From $254 per night (USD)
VRBO
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 $254 per night (USD)
VRBO
From $1177 per night (USD)
VRBO
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% 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 $1177 per night (USD)
VRBO
From $423 per night (USD)
VRBO
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 $423 per night (USD)
VRBO
$\Endless Summer\ Waterfront on the Chesapeake Bay!$
From $1099 per night (USD)
Expedia
\"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 $1099 per night (USD)
Expedia
From $684 per night (USD)
VRBO
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 $684 per night (USD)
VRBO
From $375 per night (USD)
VRBO
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Your own private 190' pier. Bring your boat and the family to this peaceful place to stay. Located on the water on Madis ...
From $375 per night (USD)
VRBO
From $463 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 $463 per night (USD)
VRBO
From $286 per night (USD)
Expedia
Lovely 3-bedroom house AC WiFi in the charming Cambridge, Great Location!!!!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover this wonderful 3-bedroom gem in Cambridge. Great location!!! This awesome house features 1 bunk bed, 1 twin bed ...
From $286 per night (USD)
Expedia

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