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

Choptank River Rentals

From $1007 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 $1007 per night (USD)
VRBO
From $281 per night (USD)
Expedia
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Bedrooms:
3
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 $281 per night (USD)
Expedia
From $393 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 $393 per night (USD)
VRBO
From $343 per night (USD)
Expedia
Waterviews, Comfort & Convenience!
Bedrooms:
3
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 $343 per night (USD)
Expedia
From $238 per night (USD)
VRBO
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 $238 per night (USD)
VRBO
From $610 per night (USD)
Expedia
Magnificent Historic Home by Water is Ready!
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
Our house, built in 1736, is ideally located in the heart of historic Cambridge. Facing the Choptank River, it is 1/2 bl ...
From $610 per night (USD)
Expedia
$Choptank Water View Cottage\/Eagle-Ironman Races with outdoor seating$
From $249 per night (USD)
VRBO
Choptank Water View Cottage\/Eagle-Ironman Races with outdoor seating
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The best kept secret, 1.5 hours from DC, 1 our to the beaches. Enjoy and relax with views of the mighty Choptank. Enjoy ...
From $249 per night (USD)
VRBO
From $263 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 $263 per night (USD)
VRBO
From $657 per night (USD)
VRBO
Downtown Oxford | Bikes | Pet Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A Quiet Escape with Water Views Around Every Turn! Bright and airy, 4-bedroom, 3-bathroom home features a first-floor b ...
From $657 per night (USD)
VRBO
From $1349 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 $1349 per night (USD)
VRBO
From $1343 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Kayaks | Pool | Private Dock
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Built in 1800, this 5-bedroom, 3-bathroom historic colonial shore house sits on 3.5+ acres and boasts endless nautical a ...
From $1343 per night (USD)
VRBO
From $722 per night (USD)
Expedia
Tilghman | Pool | Private Dock | Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Talbot County STR License# STRN-22-1 Clearview is the answer to your getaway needs. With a swimming pool, hot tub, and ...
From $722 per night (USD)
Expedia
From $514 per night (USD)
VRBO
Downtown Oxford | Charming | Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
In-town cottage with loads of charm and easy walking to parks and restaurants Tucked away in the quaint, historic town o ...
From $514 per night (USD)
VRBO
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VRBO
Waterside 4-Bedroom Chesapeake Styled Townhome
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Have fun with the whole family. Located on the grounds of a beautiful resort. This Chesapeake styled townhome features 4 ...
Click For Pricing
VRBO
From $1370 per night (USD)
VRBO
Short drive to Downtown Cambridge | Sleeps 22 | Pool | Private Dock | Kayaks | P
Bedrooms:
6
Bathrooms:
7
Sleeps:
22
Multi-Family Compound with Loads of Amenities - Pool, Beach, Beach Volleyball & More! Hudson Manor is fabulous for large ...
From $1370 per night (USD)
VRBO
From $459 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 $459 per night (USD)
Expedia
From $1265 per night (USD)
VRBO
Short drive to Downtown Cambridge | Pool | Private Dock | Game Room | Stunning V
Bedrooms:
7
Bathrooms:
7
Sleeps:
20
With over 6500 square feet of living space, tall ceilings, and spacious rooms, this modern farmhouse offers plenty of sp ...
From $1265 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
HOME ON THE RIVER: A view of Choptank River (read James Michener's 'Chesapeake') from all rooms in an airy 2 bedroom ap ...
From $245 per night (USD)
Expedia
$Historic 1918 House 1\/2 Block from the Choptank River$
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VRBO
Historic 1918 House 1\/2 Block from the Choptank River
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
This old fisherman's home in the historic district of Cambridge has been recently renovated and is close to restaurants, ...
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VRBO
From $2262 per night (USD)
Expedia
Short drive to Downtown Cambridge | Private Dock | Sleeps 22 | Pool | Hot Tub |
Bedrooms:
6
Bathrooms:
9
Sleeps:
22
When a list of vocabulary words such as 'unique', 'remarkable', and 'spectacular' still fail to describe how special a p ...
From $2262 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Relax or Play on the Choptank River!
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
B&B Use Permit No. BB 19-04 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal ...
From $236 per night (USD)
VRBO
From $1093 per night (USD)
Expedia
Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks
Bedrooms:
4
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-appo ...
From $1093 per night (USD)
Expedia
From $1140 per night (USD)
VRBO
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
TREMEZZO STAY - RANCH AT ROYAL OAK Our properties are owned, managed, and hosted by us. We deliver personally hosted lu ...
From $1140 per night (USD)
VRBO
From $621 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 $621 per night (USD)
Expedia
$Cambridge Home w\/ Private Dock ~ 4 Mi to Dtwn$
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VRBO
Cambridge Home w\/ Private Dock ~ 4 Mi to Dtwn
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Immerse yourself in the scenic views, maritime heritage, history, and art that Cambridge has to offer with a stay at thi ...
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VRBO
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Expedia
St. Michaels Area Cottage - Walk to Water & Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The 'Land of Pleasant Living' awaits your arrival at Blue Bird Cottage, a 2-bedroom, 2-bathroom Neavitt vacation rental ...
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Expedia
From $456 per night (USD)
VRBO
Algonquin on the Choptank River is a great getaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
The house is on the Choptank River with awesome views, a pier with boat lift, great fishing and water activities. The h ...
From $456 per night (USD)
VRBO
From $325 per night (USD)
Expedia
The Middle Point Cabin in Saint Michaels
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Our Talbot County Short Term Rental License Number is: ST-634-EIN 2019 Talbot County requires a minimum 3 night booking ...
From $325 per night (USD)
Expedia
From $2423 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Luxury
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Only a 15 Minute Drive to Downtown St. Michaels and Easton! Jewel of the Tred Avon | an ESVR property This 7,700 sq ft ...
From $2423 per night (USD)
VRBO
From $651 per night (USD)
Expedia
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 $651 per night (USD)
Expedia
From $901 per night (USD)
VRBO
Indian Fields - 25-Acre Nature Lovers retreat!
Bedrooms:
5
Bathrooms:
5
Sleeps:
13
Indian Fields - Twenty-five acre nature lovers retreat! Pool, Kayaks, Fire Pit - The family Dog is Welcome! Bring your ...
From $901 per night (USD)
VRBO
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Expedia
Dorchester County Home Near Choptank River!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Head to Cambridge, Maryland, for a relaxing retreat on the Eastern Shore! Located between the Choptank River and the his ...
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Expedia
From $254 per night (USD)
VRBO
Relaxation Haven on the Shore near Choptank River
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
No matter you're from a family long time no see for each other or a group of friends who miss your get togethers, Relaxa ...
From $254 per night (USD)
VRBO
From $435 per night (USD)
Expedia
Idyllic private waterfront location within walking distance to historic Oxford!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Sailor's Cottage allows you to get away from it all within walking distance of the charming and historic town of Oxford. ...
From $435 per night (USD)
Expedia
From $273 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 $273 per night (USD)
VRBO
From $1198 per night (USD)
VRBO
The Wilder Way with a beautiful pool, hot tub, and a pickleball court!!
Bedrooms:
4
Bathrooms:
6
Sleeps:
23
If you’re looking for a place to go to relax with your family and friends look no farther! Surrounded by woodland and fi ...
From $1198 per night (USD)
VRBO
From $190 per night (USD)
VRBO
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Bedrooms:
3
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 $190 per night (USD)
VRBO
$The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge$
From $279 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 $279 per night (USD)
Expedia
From $678 per night (USD)
VRBO
Minutes from Downtown Cambridge and Downtown Easton | 104+ Acre Farm
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Farmhouse Surrounded by Nature This charming 4BR, 4BA vacation home with 104+/- acres on the Choptank River is the perf ...
From $678 per night (USD)
VRBO
From $462 per night (USD)
Expedia
Downtown Cambridge | Historic Charm | Modern Upgrades
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover Your Perfect Hideaway Escape to a charming retreat where historic allure meets modern comfort! Located in the ...
From $462 per night (USD)
Expedia
From $1095 per night (USD)
VRBO
Ironman & Eagleman - 4-bedroom house in charming Cambridge.
Bedrooms:
3
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 $1095 per night (USD)
VRBO
From $276 per night (USD)
VRBO
Stay 3 nights and 4th night is free!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Fishin Franks Cottage! Located in the Waterman's community of Tilghman Island this cozy yet spacious ...
From $276 per night (USD)
VRBO
From $445 per night (USD)
VRBO
Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Create unforgettable memories by reserving your riverside retreat today! The primary bedroom features a luxurious king ...
From $445 per night (USD)
VRBO
From $278 per night (USD)
Expedia
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 $278 per night (USD)
Expedia
From $618 per night (USD)
VRBO
Turnbridge Manor
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
A waterfront property located in the heart of downtown Denton, on Maryland's Eastern Shore, the stately historic home bu ...
From $618 per night (USD)
VRBO
From $483 per night (USD)
VRBO
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
ST-605-JOH Upon arrival you realize this is the Eastern Shore Experience you have been looking for......A gated garden ...
From $483 per night (USD)
VRBO
From $231 per night (USD)
VRBO
The B&B of Anchorage - Skipjack
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
B&B Use Permit No. BB 19-04 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal ...
From $231 per night (USD)
VRBO
From $847 per night (USD)
Expedia
GORGEOUS, WATERFRONT HOME WITH POOL IS PERFECT FOR FAMILIES! WINTER DEALS NOW
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 $847 per night (USD)
Expedia
From $1049 per night (USD)
VRBO
Historic Oxford Waterfront Estate
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Bonfield Manor is located at the entrance of Oxford, a half-mile walk or bike ride to restaurants, shops and the Rivervi ...
From $1049 per night (USD)
VRBO
From $896 per night (USD)
VRBO
Renovated Historic Waterfront Home with Pool, Dock, 200 acres
Bedrooms:
5
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 $896 per night (USD)
VRBO
From $383 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 $383 per night (USD)
VRBO
From $588 per night (USD)
Expedia
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Bedrooms:
3
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 $588 per night (USD)
Expedia
From $371 per night (USD)
VRBO
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Modern 2 BR, 2 BA River House has 180-degree views of glorious sunsets Imagine two floors of picture windows overlookin ...
From $371 per night (USD)
VRBO
$BayDreams - IronMan\/Eagleman Retreat on the bay$
From $492 per night (USD)
VRBO
BayDreams - IronMan\/Eagleman Retreat on the bay
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Heavenly sunsets will dazzle you at our Chesapeake Bay vacation home. Whether you are fishing, crabbing, paddle boarding ...
From $492 per night (USD)
VRBO
From $425 per night (USD)
VRBO
Jellyfish Cottage - Spectacular Sunsets over Chesapeake Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Located on the Chesapeake Bay side of Tilghman Island, this beautiful two-story, three bedroom cottage is available for ...
From $425 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Peaceful Cambridge Home on Jenkins Creek
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
While we do not include linens/towels, we know you'll find other provided amenities, our convenient location, waterfront ...
From $371 per night (USD)
VRBO
From $214 per night (USD)
VRBO
The Anchorage B&B - The Bounty
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
B&B Use Permit No. BB 19-04 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal ...
From $214 per night (USD)
VRBO
From $318 per night (USD)
VRBO
Little Creek Hideaway - Privacy and Perfect Family Getaway.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Come relax at Little Creek Hideaway, the perfect family getaway during any season. Located just 10 minutes from Easton, ...
From $318 per night (USD)
VRBO
From $926 per night (USD)
VRBO
Hudson Creek Gorgeous Private Home Awaits your arrival. This place has it all!
Bedrooms:
5
Bathrooms:
7
Sleeps:
15
Our House is coming on the market soon - We are in the process of purchasing it and anticipating close by the end of Jun ...
From $926 per night (USD)
VRBO
From $217 per night (USD)
VRBO
5 bedroom Bed and Breakfast on the Choptank River
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
B&B Use Permit No. BB 19-04 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal ...
From $217 per night (USD)
VRBO
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VRBO
Victorian Home In Historic West End
Bedrooms:
3
Bathrooms:
6
Sleeps:
13
Victorian home in the Cambridge West End historic district. 3 blocks from water; walk to main street, & on one of the pr ...
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VRBO
From $552 per night (USD)
VRBO
Attractive Waterfront Home over looking Choptank River. Sleeps 5
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
This remolded waterfront home has a open floor plan for entertaining and comfortable living. The view of the river is f ...
From $552 per night (USD)
VRBO
From $563 per night (USD)
VRBO
Waterfront Haven in Cambridge, Md - sleeps 10, 4 bedrooms
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to our newly renovated 1920s Waterfront bungalow, where there is something for everyone. Looking for a getaway ...
From $563 per night (USD)
VRBO
From $445 per night (USD)
VRBO
BOOK NOW FOR FALL & WINTER DATES.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
STN-22-40 ONE OF OUR MOST SOUGHT AFTER PROPERTIES! MINUTES FROM ST. MICHAELS...... Peaceful retreat with breathtaking su ...
From $445 per night (USD)
VRBO
From $514 per night (USD)
VRBO
House on the Chesapeake Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Talbot County License STRN-23-41 Enjoy the beauty of the Chesapeake Bay on Tilghman Island. Enjoy fresh seafood from th ...
From $514 per night (USD)
VRBO
From $874 per night (USD)
VRBO
House close to Great Marsh Park and Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Two story Three bedroom house on tree line street half block from Great Marsh Park and Choptank River walking distance t ...
From $874 per night (USD)
VRBO
From $1015 per night (USD)
VRBO
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
From the hosts that have maintained a five star ratings on our cottage vacation rental, we would like to invite you to e ...
From $1015 per night (USD)
VRBO
From $387 per night (USD)
VRBO
Easter Weekend open WATERFRONT St Michaels area historic home, dog friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Full renovations completed in 2016 on this historic home. Sleeps four (1 King, 1 Queen, 1 Twin). Kick back, relax and e ...
From $387 per night (USD)
VRBO
$WATERFRONT!! HOT TUB!! 4 BED\/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE$
From $571 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 $571 per night (USD)
VRBO
$Hambrooks Home with Hottub\/ Mid Term stays welcomed!$
From $182 per night (USD)
Expedia
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 $182 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Beautiful Home in Historic Waterfront District, Walk to Downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
➤ Just 1 block from the water, this Spacious unique Historic Home has been Renovated & Beautifully Furnished for a comfo ...
From $291 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Beautiful Peaceful Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Look no further than this listing that offers a modern and well-built home in a safe and monitored neighborhood. The ho ...
From $398 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Stylish Victorian in Historic District
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Beware: not your typical VRBO A hunt has been set for you and your companions to follow the dramatized story of Eva Rob ...
From $409 per night (USD)
VRBO
From $1052 per night (USD)
Expedia
Waterfront retreat with heated pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
15
Beautiful, sun-filled, waterfront home where the Choptank meets the Chesapeake Bay. Water views from nearly every window ...
From $1052 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Waterfront Retreat < 4 Mi to Dtwn Cambridge!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Experience a peaceful waterfront retreat on Maryland’s eastern shore at this stunning Cambridge vacation rental! Complet ...
From $436 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Eastern Shore Waterside Cottage Near St. Michaels
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A completely renovated (2023) cottage on private wooded lot in the quaint, water side, historic community of Neavitt MD. ...
From $315 per night (USD)
Expedia
From $1053 per night (USD)
VRBO
A Waterfront Escape Like No Other
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Summary: Enjoy a weekly stay discount for open weeks in July! The Farm at Bald Eagle Point is the great escape! Our gue ...
From $1053 per night (USD)
VRBO
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VRBO
Charming Cottage on Bolingbroke Creek
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Totally Private, quiet water-front cottage with wood burning fireplace and exclusively private 60' Lap Pool(open mid-Apr ...
Click For Pricing
VRBO
From $362 per night (USD)
VRBO
Quaint Tilghman Island home
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Vacation home minutes from St Michaels. Tucked away on a quiet neighborhood street is the Wandering Loon. A pe ...
From $362 per night (USD)
VRBO
From $379 per night (USD)
VRBO
Great rates & pet friendly.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Step into a thoughtfully curated space where coastal decor meets serene comfort. The open-concept living area i ...
From $379 per night (USD)
VRBO
From $408 per night (USD)
VRBO
Cozy Home in Historic West End Perfect for Ironman
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy your getaway in historic Cambridge in our spacious & serene home. Located in the Historic West End, the home comf ...
From $408 per night (USD)
VRBO
From $271 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 $271 per night (USD)
VRBO
From $1131 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Talbot County STR License STN-22-32 This impressive 5BR, 4.5BA waterfront home was fully renovated in 2020 and provides ...
From $1131 per night (USD)
VRBO
From $500 per night (USD)
Expedia
Private townhouse for the entire family! Easy commute to the bay and beaches!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Your private townhouse will feature a large 3 story layout with 4 spacious bedrooms, 4 bathrooms, and dining area for th ...
From $500 per night (USD)
Expedia
From $384 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 $384 per night (USD)
VRBO
$New private waterfront Eastern shore home w\/ pier + peaceful water views$
From $437 per night (USD)
VRBO
New private waterfront Eastern shore home w\/ pier + peaceful water views
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to Peaceful Point! Come enjoy the beauty of the water and the serenity it brings at Peaceful Point. This perfe ...
From $437 per night (USD)
VRBO
$Luxe Chesapeake Getaway \/ 3-Bedroom Townhome$
From $398 per night (USD)
VRBO
Luxe Chesapeake Getaway \/ 3-Bedroom Townhome
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
✢ Gorgeous new townhome on the historic Cambridge waterfront ✢ Adjacent to the beautiful Downtown with shops, restaurant ...
From $398 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Duck Cove Waterfront Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR License - ST-639-DUN Come enjoy our charming, fully updated and renovated waterfront cottage located in the Eastern ...
From $366 per night (USD)
VRBO
From $280 per night (USD)
VRBO
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Looking for an Eastern Shore waterfront retreat that's perfect for a romantic long weekend, a family vacation with the k ...
From $280 per night (USD)
VRBO
From $803 per night (USD)
VRBO
Grandview - Main House
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
GRANDVIEW, which was once known as Grandview at Pleasure Point, is a private estate located on 5¼ acres of Maryland’s f ...
From $803 per night (USD)
VRBO
From $710 per night (USD)
VRBO
Downtown Oxford | Charming | Outdoor Dining
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This charming 4-bedroom, 3.5-bathroom cottage in the historic town of Oxford was designed with your vacation in mind. Th ...
From $710 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Tilghman | Fenced Yard | Pet Friendly | Charming
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Talbot County STR License #STN-22-20 This 3-bedroom, 2-bathroom Tilghman Island water view retreat offers a character-f ...
From $444 per night (USD)
Expedia
From $1340 per night (USD)
VRBO
NEW! Gorgeous Waterfront Estate with pool, beach and dock
Bedrooms:
6
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 $1340 per night (USD)
VRBO
From $2192 per night (USD)
Expedia
Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier
Bedrooms:
4
Bathrooms:
6
Sleeps:
22
7 Night Peak and 2 Night Shoulder Minimum Stay! 10% Discount for Weekly Rental! Oyster Season starts October 1st! Sle ...
From $2192 per night (USD)
Expedia
$Cambridge Beach Home on Choptank River w\/ Pier!$
From $677 per night (USD)
VRBO
Cambridge Beach Home on Choptank River w\/ Pier!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Your next waterfront retreat awaits at this 5-bedroom, 3-bath Cambridge vacation rental! This lovely property features 5 ...
From $677 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Stylish Home on the Choptank River (with Tidal Beach)
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to the River House! Stay in our renovated salt-box style home on the Choptank River of Maryland's Eastern Shore, ...
From $264 per night (USD)
Expedia
From $557 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Waterfront Oasis of Peace and Relaxation! This 3-bedroom, 2-bathroom offers an open floor plan character-filled inter ...
From $557 per night (USD)
VRBO
$Family-Friendly Cambridge Home w\/ Fire Pit!$
From $375 per night (USD)
Expedia
Family-Friendly Cambridge Home w\/ Fire Pit!
Bedrooms:
3
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 $375 per night (USD)
Expedia
From $1633 per night (USD)
VRBO
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Bedrooms:
6
Bathrooms:
7
Sleeps:
12
Talbot County STR License STRN-23-10 This newly renovated coastal 7-bedroom, 6-bathroom waterfront getaway with a spa-l ...
From $1633 per night (USD)
VRBO
From $660 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Shorely, this is a true outdoor paradise! Originally a waterman's cottage, Neavitt Cottage has been tastefully updated ...
From $660 per night (USD)
Expedia

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Results: 149 Rentals