Choptank River Rentals
- From $175 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 $175 per night (USD)VRBO
- From $350 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 $350 per night (USD)Expedia
- From $165 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 $165 per night (USD)VRBO
- From $499 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 $499 per night (USD)Expedia
- From $240 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 $240 per night (USD)VRBO
- From $291 per night (USD)
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 ...
From $291 per night (USD)Expedia
- From $197 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 $197 per night (USD)VRBO
- From $434 per night (USD)
Expedia
Cozy Cambridge Retreat w\/ Casita Near Marina!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Your next family retreat awaits at this 4-bedroom, 3-bath home featuring a spacious casita! With its central location, t ...
From $434 per night (USD)Expedia
- From $1092 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 $1092 per night (USD)VRBO
- From $361 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 $361 per night (USD)Expedia
- From $1853 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 $1853 per night (USD)VRBO
- From $423 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 $423 per night (USD)Expedia
- Click For Pricing
Expedia
Charming and Private with a Water view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This thoughtfully furnished, cozy 1 bedroom house is an ideal love nest or quiet retreat for writers, artists, nature lo ...
Click For PricingExpedia
- From $750 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 $750 per night (USD)Expedia
- From $1499 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 $1499 per night (USD)VRBO
- From $595 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 $595 per night (USD)Expedia
- From $362 per night (USD)
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 ...
From $362 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- Click For Pricing
Expedia
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
Welcome to our year-round waterfront retreat on 5 acres with breathtaking views on Hudson Creek. Perfect for family reun ...
Click For PricingExpedia
- From $222 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 $222 per night (USD)Expedia
- Click For Pricing
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, ...
Click For PricingVRBO
- From $1869 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 $1869 per night (USD)Expedia
- From $210 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 $210 per night (USD)VRBO
- From $760 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 $760 per night (USD)Expedia
- From $590 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 $590 per night (USD)VRBO
- From $320 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 $320 per night (USD)Expedia
- Click For Pricing
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 PricingVRBO
- From $1243 per night (USD)
Expedia
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 $1243 per night (USD)Expedia
- From $305 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 $305 per night (USD)VRBO
- From $1154 per night (USD)
Expedia
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 $1154 per night (USD)Expedia
- From $506 per night (USD)
VRBO
Downtown Oxford | Boat Slip | Bikes | Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bright and airy, 4-bedroom, 3-bathroom home features a first-floor bedroom with bath as well as an updated gourmet kitch ...
From $506 per night (USD)VRBO
- From $950 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 $950 per night (USD)VRBO
- From $900 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 $900 per night (USD)VRBO
- From $685 per night (USD)
VRBO
Large Luxury Townhouse with Elevator adjacent to the Chesapeake Hyatt
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a 4 Bedroom, 3.5 Bath LUXURY townhouse overlooking the 1st hole of the RiverMarsh Golf Course at the Hyatt Regency ...
From $685 per night (USD)VRBO
- From $922 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 $922 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Waterfront Getaway on the Choptank River
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedroom 1 bath home situated on 2 acres. Home comes equipped with sleeper sofa and all the outdoor possibilities the w ...
From $250 per night (USD)VRBO
- From $399 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 $399 per night (USD)VRBO
- From $799 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 $799 per night (USD)VRBO
- From $195 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 $195 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $400 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 $400 per night (USD)VRBO
- From $425 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 $425 per night (USD)VRBO
- From $205 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 $205 per night (USD)VRBO
- From $480 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 $480 per night (USD)VRBO
- From $405 per night (USD)
VRBO
Modernized classic. Historic district near water.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Well maintained and modernized classic home 3 blocks from the Great Marsh Park on the Choptank River A short walk to dow ...
From $405 per night (USD)VRBO
- From $800 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 $800 per night (USD)VRBO
- Click For Pricing
Expedia
Waterfront Vintage Eastern Shore Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Cedar Grove Beach is a lovely vintage Eastern Shore property perfect for a family vacation or a group of friends to get ...
Click For PricingExpedia
- From $269 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 $269 per night (USD)VRBO
- From $570 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 $570 per night (USD)VRBO
- From $475 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 $475 per night (USD)VRBO
- From $345 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 $345 per night (USD)VRBO
- From $435 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 $435 per night (USD)VRBO
- From $361 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 $361 per night (USD)VRBO
- From $375 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 $375 per night (USD)VRBO
- From $524 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 $524 per night (USD)VRBO
- From $250 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 $250 per night (USD)Expedia
- From $210 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 $210 per night (USD)VRBO
- From $809 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 $809 per night (USD)Expedia
- From $986 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 $986 per night (USD)VRBO
- From $845 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 $845 per night (USD)VRBO
- From $239 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 $239 per night (USD)VRBO
- From $750 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 $750 per night (USD)Expedia
- From $404 per night (USD)
VRBO
BOOKING FALL & WINTER-ACT NOW FOR BEST AVAILABILITY!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ST-217-HARG Within minutes of historic St Michaels this 4 BEDROOM waterfront home is located on Tilghman Island. A wat ...
From $404 per night (USD)VRBO
- From $591 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 $591 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Stylish Victorian in Historic District
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the heart of the peaceful Historic District of Cambridge, this Victorian stunner c. 1912 is the place to book ...
From $300 per night (USD)VRBO
- Click For Pricing
Expedia
Waterfront retreat with heated pool, historic guest house.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Beautiful, sun-filled, waterfront home where the Choptank meets the Chesapeake Bay. Water views from nearly every window ...
Click For PricingExpedia
- From $463 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 $463 per night (USD)VRBO
- Click For Pricing
Expedia
Charmer Base for Eastern Shore Exploration
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful Vintage Farm House apartment located right in the mid of the Eastern Shore Peninsular, with its unique lo ...
Click For PricingExpedia
- From $297 per night (USD)
VRBO
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 $297 per night (USD)VRBO
- From $1104 per night (USD)
VRBO
A Waterfront Escape Like No Other
- 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 $1104 per night (USD)VRBO
- From $360 per night (USD)
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 ...
From $360 per night (USD)VRBO
- From $275 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 $275 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Warmth and Comfort Await
- 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 $295 per night (USD)VRBO
- Click For Pricing
Expedia
Your “Happy Place”-Updated beautifully 3 story home on quiet island
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
An amazing escape on the Chesapeake Bay. Explore Tilghman Island by bike or boat. Enjoy fresh seafood from the local se ...
Click For PricingExpedia
- From $219 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 $219 per night (USD)VRBO
- From $333 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 $333 per night (USD)VRBO
- From $398 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 $398 per night (USD)VRBO
- From $243 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 $243 per night (USD)VRBO
- From $334 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 $334 per night (USD)VRBO
- From $325 per night (USD)
Expedia
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 $325 per night (USD)Expedia
- From $850 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 $850 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 $340 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 $340 per night (USD)VRBO
- From $775 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 $775 per night (USD)VRBO
- From $289 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 $289 per night (USD)VRBO
- From $1697 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 $1697 per night (USD)Expedia
- From $656 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 $656 per night (USD)VRBO
- From $599 per night (USD)
Expedia
6BD 3BA Home walking distance to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 12
We invite you to reserve our property. A meticulously restored historic home with modern amenities. The largest square ...
From $599 per night (USD)Expedia
- From $185 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 newly renovated salt-box style home on the Choptank River of Maryland's Eastern ...
From $185 per night (USD)VRBO
- From $318 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County STR License #ST-578-shi This 3-bedroom, 2-bathroom offers an open floor plan character-filled interior an ...
From $318 per night (USD)Expedia
- From $288 per night (USD)
VRBO
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 $288 per night (USD)VRBO
- Click For Pricing
Expedia
Ridgely Waterfront | Private Dock | Kayaks | Game Room | Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom, 2.5-bathroom waterfront on the Delmarva Peninsula is the perfect spot for a relaxing vacation. Truly exc ...
Click For PricingExpedia
- From $1215 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 $1215 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Waterfront, cozy cottage with private pool on 27 acres of privacy
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private 27 acre estate is nestled a mere 200 feet from the banks of the Choptank River. Whether you have ha ...
From $325 per night (USD)Expedia
- From $916 per night (USD)
VRBO
Short drive to Downtown Cambridge | Private Dock | Kayaks | 1000 Ft of Shoreline
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
This beautifully renovated 6-bedroom, 4.5-bathroom waterfront property with direct access to the Choptank River where yo ...
From $916 per night (USD)VRBO
- Click For Pricing
Expedia
Historic Cambridge Home: Near Choptank River!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Situated in the historic ‘West End’ of Cambridge, this 3-bedroom, 2-bath vacation rental has it all! ‘Cambridge Cottage’ ...
Click For PricingExpedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $1143 per night (USD)
Expedia
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Welcome to Juniper Cove! Large luxury waterfront home on 15 private acres, with a large in-ground salt water pool in Ca ...
From $1143 per night (USD)Expedia
- From $426 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 $426 per night (USD)VRBO
- From $450 per night (USD)
Expedia
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 $450 per night (USD)Expedia