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 $960 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 $960 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 $299 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 $299 per night (USD)
VRBO
From $698 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 $698 per night (USD)
VRBO
From $354 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 $354 per night (USD)
VRBO
$1915 Historic Cambridge Property w\/ Fire Pit!$
From $462 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 $462 per night (USD)
Expedia
From $368 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 $368 per night (USD)
VRBO
From $632 per night (USD)
VRBO
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 $632 per night (USD)
VRBO
From $1835 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 $1835 per night (USD)
VRBO
From $533 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 $533 per night (USD)
Expedia
From $1036 per night (USD)
VRBO
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 $1036 per night (USD)
VRBO
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 $995 per night (USD)
VRBO
Breathtaking Views & Tranquility
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Summary: STRN-22-23 Wonderful waterfront home. Minutes from St. Michaels offering all you'll need for the perfect vacati ...
From $995 per night (USD)
VRBO
From $570 per night (USD)
Expedia
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)
Expedia
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
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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 ...
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Expedia
From $550 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 $550 per night (USD)
VRBO
From $518 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 $518 per night (USD)
VRBO
From $250 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 $250 per night (USD)
VRBO
From $1499 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 $1499 per night (USD)
Expedia
$BayDreams - IronMan\/Eagleman Retreat on the bay$
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 $375 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 $375 per night (USD)
VRBO
From $363 per night (USD)
VRBO
Peaceful Cambridge Home on Jenkins Creek
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We provide linens and towels from February through April. While we do not otherwise include linens/towels, we know you' ...
From $363 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
$Cambridge Home w\/ Private Dock ~ 4 Mi to Dtwn$
From $398 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 $398 per night (USD)
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 $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 $426 per night (USD)
Expedia
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)
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
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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 ...
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Expedia
From $1586 per night (USD)
VRBO
Breathtaking Waterfront Estate
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Summary: Durham-Hythe Estate is nestled within 7.5 acres of idyllic grounds with its own 750ft shoreline, 75ft private d ...
From $1586 per night (USD)
VRBO
From $490 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 $490 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
From $213 per night (USD)
VRBO
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 $213 per night (USD)
VRBO
$Historic 1918 House 1\/2 Block from the Choptank River$
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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, ...
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Expedia
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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 ...
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Expedia
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
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VRBO
Sunny Home in Cambridge Historic District
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Renovated home in Cambridge's Historic District, just two blocks from the Choptank River, 3.5 blocks from Gerry Boyle Pa ...
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VRBO
From $2135 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 $2135 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 $745 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 $745 per night (USD)
Expedia
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 $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 $500 per night (USD)
VRBO
Last guest said property was AMAZING.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: ST-557-LEE Just minutes from St. Michaels is the perfect get away. Start your day with a walk over to the loca ...
From $500 per night (USD)
VRBO
$Family-Friendly Cambridge Home w\/ Fire Pit!$
From $287 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 $287 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $1262 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 $1262 per night (USD)
Expedia
From $706 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 $706 per night (USD)
VRBO
From $367 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 $367 per night (USD)
Expedia
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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 ...
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VRBO
From $418 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 $418 per night (USD)
VRBO
From $928 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 $928 per night (USD)
VRBO
From $916 per night (USD)
Expedia
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)
Expedia
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VRBO
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’ ...
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VRBO
From $450 per night (USD)
VRBO
Waterfront Bliss, Spectacular Views, NEW RATES
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Wake to the sun rising over Harris Creek, where breathtaking views meet unparalleled tranquility. Nestled along ...
From $450 per night (USD)
VRBO
From $504 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 $504 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Talbot County STR License #ST-643-DER Originally a waterman's cottage, Neavitt Cottage has been tastefully updated (sup ...
From $473 per night (USD)
Expedia
From $442 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 $442 per night (USD)
VRBO
From $943 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 $943 per night (USD)
Expedia
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 ...
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VRBO
From $417 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 $417 per night (USD)
VRBO
From $409 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 $409 per night (USD)
VRBO
From $1050 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 $1050 per night (USD)
VRBO
From $599 per night (USD)
VRBO
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)
VRBO
From $205 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 newly renovated salt-box style home on the Choptank River of Maryland's Eastern ...
From $205 per night (USD)
Expedia
From $321 per night (USD)
VRBO
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 $321 per night (USD)
VRBO
From $944 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 $944 per night (USD)
Expedia
From $706 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 $706 per night (USD)
VRBO
From $889 per night (USD)
Expedia
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 $889 per night (USD)
Expedia
$Cambridge Beach Home on Choptank River w\/ Pier!$
From $567 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 $567 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Time to make those summer plans!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: STN-22-12 This waterman's community is rich in the traditions of working on the water. The spirit of Tilghman ...
From $250 per night (USD)
VRBO
From $200 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 $200 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 $290 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 $290 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 $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 $500 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 $500 per night (USD)
Expedia
From $281 per night (USD)
VRBO
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 $281 per night (USD)
VRBO
From $907 per night (USD)
Expedia
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 $907 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 $744 per night (USD)
Expedia
Minutes from Downtown Cambridge | Outdoor Dining | Private Dock | Kayaks | Bikes
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
This gorgeous two-story 5,000 square foot, 4-bedroom, 3.5-bathroom waterfront estate was designed with your comfort in m ...
From $744 per night (USD)
Expedia
From $600 per night (USD)
VRBO
Private 9 acre Family Retreat on the Chesapeake Bay
Bedrooms:
5
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 $600 per night (USD)
VRBO
$Luxe Chesapeake Getaway \/ 3-Bedroom Townhome$
From $303 per night (USD)
Expedia
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 $303 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Stylish Victorian in Historic District
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Located in the heart of the peaceful Historic District of Cambridge, this Victorian stunner c. 1912 is the place to book ...
From $307 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 Pricing
Expedia
From $406 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 $406 per night (USD)
VRBO
From $803 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 $803 per night (USD)
Expedia
From $500 per night (USD)
VRBO
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)
VRBO
From $271 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 $271 per night (USD)
Expedia
$Cozy Cottage with Private Dock- Chesapeake Bay\/ Cambridge (Pet-Friendly)$
From $371 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 $371 per night (USD)
VRBO
From $449 per night (USD)
VRBO
Entire Updated Waterview Home in Cambridge, MD
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
➤ Waterview home with breathtaking views of Pinks Pond & the Choptank River. ★ This home is ideally located on a quiet ...
From $449 per night (USD)
VRBO
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 $950 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 $950 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
Click For Pricing
Expedia
Sunset Vista | an ESVR property
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Eastern Shore Vacation Rentals presents Sunset Vista. Cross the historic Tilghman Island bridge and experience the adven ...
Click For Pricing
Expedia
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

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Results: 143 Rentals