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 $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)Expedia
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)Expedia
From $258 per night (USD)VRBO
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)VRBO
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)VRBO
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)VRBO
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 $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 $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 $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)VRBO
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)VRBO
From $722 per night (USD)Expedia
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)Expedia
From $347 per night (USD)VRBO
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)VRBO
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 $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
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 $1196 per night (USD)VRBO
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)VRBO
From $339 per night (USD)Expedia
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)Expedia
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 PricingExpedia
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 PricingExpedia
From $2125 per night (USD)VRBO
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)VRBO
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)VRBO
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)VRBO
From $829 per night (USD)Expedia
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)Expedia
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 $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 $473 per night (USD)VRBO
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)VRBO
From $430 per night (USD)Expedia
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)Expedia
From $817 per night (USD)VRBO
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)VRBO
From $807 per night (USD)Expedia
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)Expedia
From $908 per night (USD)VRBO
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)VRBO
From $1364 per night (USD)Expedia
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)Expedia
From $380 per night (USD)VRBO
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)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 $392 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 $392 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 $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 $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
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 $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 $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 $333 per night (USD)VRBO
Aurora Blue - A Stylish Experience
- 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 $333 per night (USD)VRBO
From $1119 per night (USD)Expedia
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 $1119 per night (USD)Expedia
From $412 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 $412 per night (USD)VRBO
From $666 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 $666 per night (USD)VRBO
From $185 per night (USD)VRBO
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 $185 per night (USD)VRBO
From $434 per night (USD)Expedia
Walk to Dtwn! Waterfront 3BR Cambridge Townhome
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Deck Overlooking the Marina | Home Office | Community Pool in Summer Embrace Eastern Shore living with a stay at this m ...
From $434 per night (USD)Expedia
From $148 per night (USD)VRBO
Pet-Friendly Pond Cottage • Nature Escape Near Beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your peaceful lakeside retreat. Escape the crowds and unwind in this charming waterfront cottage nestled amo ...
From $148 per night (USD)VRBO
From $494 per night (USD)Expedia
Waterfront Fishing Creek Cottage with Guesthouse Pier-Kayaks-Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a peaceful stay at this 2 bedroom cottage with bonus 1 bedroom guesthouse in Woolford that is near Cambridge and t ...
From $494 per night (USD)Expedia
From $367 per night (USD)VRBO
Hoopers Landing | Private Dock | Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Hoopers Landing, a delightful coastal cottage on the cheerful waterfront of Upper Hoopers Island, the first o ...
From $367 per night (USD)VRBO
From $549 per night (USD)Expedia
Blackwater Bend | Waterfront Pool, Dock & Farm
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Blackwater Bend! Sika deer and bald eagles in the front yard, the Little Blackwater out back, and 70 acres of ...
From $549 per night (USD)Expedia
From $165 per night (USD)VRBO
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Pint-Sized on Poplar — a stylishly appointed micro-loft in the heart of downtown Cambridge, MD, sitting direc ...
From $165 per night (USD)VRBO
From $767 per night (USD)VRBO
Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Riverside Haven — a beautifully designed waterfront retreat in the sought-after Deep Harbor community in Camb ...
From $767 per night (USD)VRBO
From $938 per night (USD)VRBO
Rippling Waters on Fishing Creek
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Rippling Waters on Fishing Creek, a beautifully remodeled waterfront retreat on Maryland’s Eastern Shore. Thi ...
From $938 per night (USD)VRBO
From $1452 per night (USD)Expedia
Chesapeake Bay Retreat
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Chesapeake Bay Retreat offers a tranquil escape on the Bay with stunning sunsets and ocean liner views. Guests will enjo ...
From $1452 per night (USD)Expedia
From $383 per night (USD)VRBO
Stunning Bay Views, Abundant Wildlife, Great Fishing & Easy Boating Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
A Peaceful Retreat in the Heart of Madison, MD Welcome to your perfect getaway. Nestled on a serene 1‑acre lot, this ...
From $383 per night (USD)VRBO
From $599 per night (USD)VRBO
BOAT FISH CRAB SWIM RELAX! WELCOME TO YOUR EASTERN SHORE WATERFRONT ESCAPE!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Nestled on 1½ beautifully landscaped waterfront acres with over 460' of shoreline, this private retreat offers the perfe ...
From $599 per night (USD)VRBO
From $739 per night (USD)VRBO
Waterfront Retreat on Maryland's Eastern Shore
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Wake up to breathtaking water views, enjoy your morning coffee as the sun rises over the bay, and spend your days fishin ...
From $739 per night (USD)VRBO
From $847 per night (USD)Expedia
Eastern Shore Getaway - Cambridge, Maryland
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Bring the whole family to this great place with lots of room for fun. Centered in the beautiful, historic town of Cambri ...
From $847 per night (USD)Expedia
From $284 per night (USD)VRBO
Comfort by the Creek
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Single family home located on quiet cul-de-sac with access to creek via community pier. This beautiful property is the p ...
From $284 per night (USD)VRBO
From $691 per night (USD)Expedia
Modern Chesapeake Waterfront - Heated Pool - Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Chesapeake Dream is a stunning renovated waterfront farmhouse on 5.6 acres with breathtaking Chesapeake Bay vi ...
From $691 per night (USD)Expedia
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Lovely Newly Renovated 3 Bed House Walk to IronMan with Off-Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to our lovely and spacious home in Cambridge with 3 bedrooms and a den that will allow you to get ready to race, ...
Click For PricingVRBO
From $447 per night (USD)Expedia
Walk to Cambridge Waterfront: Townhome w/ Deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Community Pool Access | EV Charger | On-Site Harbor Walk & Marina Experience the ultimate Eastern Shore escape at this ...
From $447 per night (USD)Expedia
From $2224 per night (USD)VRBO
Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 28
“Captains Quarters on the Bay” is the perfect place for large family reunions, corporate and religious retreats during ...
From $2224 per night (USD)VRBO