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
$\Belle Aire Landing\ a Large Beautiful Waterfront Estate! Under New Management!$
From $2484 per night (USD)
Expedia
\"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 $2484 per night (USD)
Expedia
From $411 per night (USD)
VRBO
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 $411 per night (USD)
VRBO
From $393 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 $393 per night (USD)
Expedia
From $343 per night (USD)
VRBO
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)
VRBO
From $334 per night (USD)
Expedia
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 $334 per night (USD)
Expedia
From $610 per night (USD)
VRBO
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)
VRBO
From $256 per night (USD)
Expedia
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 $256 per night (USD)
Expedia
From $928 per night (USD)
VRBO
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 $928 per night (USD)
VRBO
From $541 per night (USD)
Expedia
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 $541 per night (USD)
Expedia
From $666 per night (USD)
VRBO
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 $666 per night (USD)
VRBO
From $1595 per night (USD)
Expedia
Short drive to Downtown Cambridge | Pool | Private Dock | Game Room | Stunning V
Bedrooms:
7
Bathrooms:
8
Sleeps:
20
Waterfront Farmhouse Surrounded by Nature With over 6500 square feet of living space, tall ceilings, and spacious rooms ...
From $1595 per night (USD)
Expedia
From $1228 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 $1228 per night (USD)
VRBO
From $1218 per night (USD)
Expedia
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 $1218 per night (USD)
Expedia
From $2384 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 $2384 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Beautiful Colonial Home on the Choptank River
Bedrooms:
2
Bathrooms:
5
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 $470 per night (USD)
Expedia
From $398 per night (USD)
VRBO
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 $398 per night (USD)
VRBO
From $2449 per night (USD)
Expedia
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 $2449 per night (USD)
Expedia
From $684 per night (USD)
VRBO
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
We would like to welcome you to our charming getaway. This is the ideal spot for families, friends, or business retreats ...
From $684 per night (USD)
VRBO
From $992 per night (USD)
Expedia
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 $992 per night (USD)
Expedia
From $307 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 $307 per night (USD)
VRBO
From $1240 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-app ...
From $1240 per night (USD)
Expedia
Click For Pricing
VRBO
Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm
Bedrooms:
1
Bathrooms:
3
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 ...
Click For Pricing
VRBO
$Historic 1918 House 1\/2 Block from the Choptank River$
Click For Pricing
Expedia
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, ...
Click For Pricing
Expedia
From $260 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 $260 per night (USD)
VRBO
From $440 per night (USD)
Expedia
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 $440 per night (USD)
Expedia
From $235 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 $235 per night (USD)
VRBO
From $1174 per night (USD)
Expedia
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Rentals between June 13 - August 22 start Fridays; 5-night minimum; 10% discount for full week. Pets permitted ...
From $1174 per night (USD)
Expedia
From $604 per night (USD)
VRBO
Time Stands Still At the Dock.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Minutes from St Michaels, this peaceful retreat will have guests never wanting to leave. Panoramic views of the ...
From $604 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:
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 $223 per night (USD)
Expedia
$The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge$
From $426 per night (USD)
VRBO
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 $426 per night (USD)
VRBO
From $709 per night (USD)
Expedia
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 $709 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 $1069 per night (USD)
Expedia
Attention Racers - Beautiful Home 3 Blocks from Great Marsh Park!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This beautifully appointed 2-story house is 3 blocks from Gerry Boyle Park for an easy walk to the race start/finish and ...
From $1069 per night (USD)
Expedia
From $1221 per night (USD)
VRBO
Downtown Oxford | Private Beach | Private Pool | Luxury
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Luxury awaits at The Beach House, a stunning 4-bedroom, 4.5-bathroom vacation extravaganza in the vibrant Oxford neighbo ...
From $1221 per night (USD)
VRBO
$Aurora Blue - A Stylish Experience \n$
From $349 per night (USD)
Expedia
Aurora Blue - A Stylish Experience \n
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Stylish experience at the centrally located retreat. New owners purchased East and renovated the entire home both inside ...
From $349 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Pet-Friendly Cottage – Ideal for Summer Getaways!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Fishin Frank's Cottage on Tilghman Island Tucked away in the charming Watermans community of Tilghm ...
From $368 per night (USD)
VRBO
From $319 per night (USD)
Expedia
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 $319 per night (USD)
Expedia
From $249 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 $249 per night (USD)
VRBO
From $518 per night (USD)
Expedia
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 $518 per night (USD)
Expedia
From $360 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 $360 per night (USD)
VRBO
From $561 per night (USD)
Expedia
House on the Chesapeake Bay
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Talbot County License STRN-23-41 Enjoy the beauty of the Chesapeake Bay on Tilghman Island. Enjoy fresh seafood from th ...
From $561 per night (USD)
Expedia
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 $388 per night (USD)
Expedia
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 $388 per night (USD)
Expedia
$BayDreams - IronMan\/Eagleman Retreat on the bay$
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)
Expedia
Jellyfish Cottage - Waterfront. 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)
Expedia
From $398 per night (USD)
VRBO
Peaceful Cambridge Home on Jenkins Creek
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
While we do not include linens/towels (EXCEPT DURING THE MONTHS OF JANUARY THROUGH APRIL!), we know you'll find other pr ...
From $398 per night (USD)
VRBO
From $998 per night (USD)
Expedia
Gorgeous, Waterfront Home -- Perfect for Families and Large Groups -- Lots to Do
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 $998 per night (USD)
Expedia
From $562 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 $562 per night (USD)
VRBO
From $536 per night (USD)
Expedia
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 $536 per night (USD)
Expedia
From $296 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 $296 per night (USD)
VRBO
From $1049 per night (USD)
Expedia
Historic Oxford Waterfront Estate
Bedrooms:
6
Bathrooms:
7
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)
Expedia
From $807 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 $807 per night (USD)
VRBO
From $339 per night (USD)
Expedia
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 $339 per night (USD)
Expedia
From $925 per night (USD)
VRBO
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 $925 per night (USD)
VRBO
From $1044 per night (USD)
Expedia
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
FALL SPECIAL BOOK 3 NIGHTS AND GET A 1 BUSHEL OF CRABS FREE From the hosts that have maintained a five star ratings on ...
From $1044 per night (USD)
Expedia
From $565 per night (USD)
VRBO
The Water's Edge Rental 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 $565 per night (USD)
VRBO
From $285 per night (USD)
Expedia
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 $285 per night (USD)
Expedia
From $558 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 $558 per night (USD)
VRBO
From $500 per night (USD)
Expedia
BOOK NOW FOR SPRING & SUMMER 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 $500 per night (USD)
Expedia
From $457 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 $457 per night (USD)
VRBO
From $407 per night (USD)
Expedia
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 $407 per night (USD)
Expedia
From $1113 per night (USD)
VRBO
Waterfront retreat, beautiful views!
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 $1113 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Waterfront Retreat < 4 Mi to Dtwn Cambridge!
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Experience a peaceful waterfront retreat on Maryland’s eastern shore at this stunning Cambridge vacation rental! Complet ...
From $515 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Eastern Shore Waterside Cottage Near St. Michaels
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to an idyllic retreat, nestled in the peaceful town of Neavitt, just a short drive from the charming village of ...
From $396 per night (USD)
VRBO
From $1431 per night (USD)
Expedia
Time Stands Still, While Memories Are Made.
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Summary: The Farm at Bald Eagle Point is the great escape! Our guests can settle in and never have to leave this exclusi ...
From $1431 per night (USD)
Expedia
From $352 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 $352 per night (USD)
VRBO
From $403 per night (USD)
Expedia
4-Bedroom Retreat: Modern, Pet-Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Heart of the Island & Pet Friendly Retreat on Tilghman Island! Step into a thoughtfully curated space where coa ...
From $403 per night (USD)
Expedia
$WATERFRONT!! HOT TUB!! 4 BED\/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE$
From $664 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 $664 per night (USD)
VRBO
$Hambrooks Home with Hottub\/ Mid Term stays welcomed!$
From $206 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 $206 per night (USD)
Expedia
From $1243 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 $1243 per night (USD)
VRBO
From $581 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 $581 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Tilghman Island Retreat By Knapps Narrows!
Bedrooms:
2
Bathrooms:
4
Sleeps:
4
Furnished Sunroom | Family Friendly | Half-Mi to Marina Make your way to this lovely Tilghman Island vacation rental, i ...
From $292 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Walk to Dtwn: Waterfront Eastern Shore Townhome!
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Game Room | Scenic Waterfront Deck | Community Pool | Pet Friendly w/ Fee | EV Charger Experience life in the heart of ...
From $387 per night (USD)
Expedia
From $1406 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 $1406 per night (USD)
VRBO
From $1096 per night (USD)
Expedia
Escape to The Beach House - Your Waterfront Oasis Awaits!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Discover paradise at The Beach House, a stunning waterfront rental offered by Tidewater Vacations. Nestled along the ser ...
From $1096 per night (USD)
Expedia
From $164 per night (USD)
VRBO
Cambridge Apt in Walkable Neighborhood
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Waterfront Setting | Close to Local Eats Explore the quiet side of the Chesapeake Bay with your closest travel buddy at ...
From $164 per night (USD)
VRBO
From $359 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 $359 per night (USD)
Expedia
From $345 per night (USD)
VRBO
A little slice of heaven on the Choptank River Sept 19 to 23 is now open
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 $345 per night (USD)
VRBO
From $366 per night (USD)
Expedia
Duck Cove Waterfront Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR License - STRN-24-52 Come enjoy our charming, fully updated and renovated waterfront cottage located in the Eastern ...
From $366 per night (USD)
Expedia
From $456 per night (USD)
VRBO
New, Intown Waterfront Townhome wPool & Location!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Perfect, large property for an extended, family or group stay at this superb Chesapeake retreat -- part of a ga ...
From $456 per night (USD)
VRBO
From $907 per night (USD)
Expedia
Stunning Waterfront Escape with New Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Whether you're looking to relax poolside or explore the surrounding area, this waterfront home has everything y ...
From $907 per night (USD)
Expedia
From $254 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 $254 per night (USD)
VRBO
From $1195 per night (USD)
Expedia
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 $1195 per night (USD)
Expedia
From $363 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 $363 per night (USD)
VRBO
From $892 per night (USD)
Expedia
Grandview - Main House
Bedrooms:
3
Bathrooms:
5
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 $892 per night (USD)
Expedia
From $724 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 $724 per night (USD)
VRBO
From $443 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 $443 per night (USD)
Expedia
From $1895 per night (USD)
VRBO
NEW! Gorgeous Waterfront Estate with Saltwater 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 $1895 per night (USD)
VRBO
From $1703 per night (USD)
Expedia
Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier
Bedrooms:
4
Bathrooms:
7
Sleeps:
22
7 Night Peak and 3 Night Shoulder Minimum Stay! 10% Discount for Weekly Rental! Crab Season starts April 1st! Sleeps ...
From $1703 per night (USD)
Expedia
$Cozy Cottage with Private Dock- Chesapeake Bay\/ Cambridge (Pet-Friendly)$
From $386 per night (USD)
VRBO
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 $386 per night (USD)
VRBO
From $653 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 $653 per night (USD)
Expedia
From $272 per night (USD)
VRBO
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 $272 per night (USD)
VRBO
From $547 per night (USD)
Expedia
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 $547 per night (USD)
Expedia
$Choptank River Beach Home w\/ Pier in Cambridge!$
From $703 per night (USD)
VRBO
Choptank River Beach Home w\/ Pier in Cambridge!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Riverfront Location | In-Unit Washer & Dryer | Gas Grill for Group Cookouts Your next waterfront retreat awaits at thi ...
From $703 per night (USD)
VRBO
$1915 Historic Cambridge Property w\/ Fire Pit!$
From $445 per night (USD)
Expedia
1915 Historic Cambridge Property w\/ Fire Pit!
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
Experience the deep-rooted history of Cambridge when you book this 5-bedroom, 3.5-bathroom vacation rental. This ideally ...
From $445 per night (USD)
Expedia
From $478 per night (USD)
VRBO
Historic Renovated Jackrabbit Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make some memories at this unique and family-friendly 19th Century farmhouse. Relax, ride bikes a few short blocks to th ...
From $478 per night (USD)
VRBO
$Waterfront, cozy cottage with private pool on 27 acres \n\n\n\n\n\n$
From $360 per night (USD)
Expedia
Waterfront, cozy cottage with private pool on 27 acres \n\n\n\n\n\n
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
FALL SPECIAL BOOK 3 NIGHTS AND GET A 1/2 BUSHEL OF CRABS FREE Located on a private 27 acre estate is nestled a mere 200 ...
From $360 per night (USD)
Expedia
$Family-Friendly Cambridge Home w\/ Fire Pit!$
From $391 per night (USD)
VRBO
Family-Friendly Cambridge Home w\/ Fire Pit!
Bedrooms:
3
Bathrooms:
4
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 $391 per night (USD)
VRBO
From $1647 per night (USD)
Expedia
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 $1647 per night (USD)
Expedia

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Results: 138 Rentals