Talbot Area Rentals
From $262 per night (USD)VRBO
Harbor View Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This unique space has amazing appeal. Within walking distance of every point of interest in Saint Michaels; including th ...
From $262 per night (USD)VRBO
From $241 per night (USD)Expedia
Adorable two-bedroom retreat close to Easton, Denton, Centreville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax in this quiet, renovated bungalow just a short bike ride to Tuckahoe State Park, the Eastern Shore's largest state ...
From $241 per night (USD)Expedia
From $1312 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 $1312 per night (USD)VRBO
From $527 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 $527 per night (USD)Expedia
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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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From $453 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 $453 per night (USD)Expedia
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 $2166 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 $2166 per night (USD)Expedia
From $1095 per night (USD)VRBO
Ironman & Eagleman - 4-bedroom house in charming Cambridge.
- Bedrooms:
- 2
- 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 $354 per night (USD)Expedia
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy historic Cambridge all year at this fully stocked and freshly renovated 2 bedroom, 2.5 bath townhouse across the s ...
From $354 per night (USD)Expedia
From $413 per night (USD)VRBO
Aurora Blue - A Stylish Experience \n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stylish experience at the centrally located retreat. New owners purchased East and renovated the entire home both inside ...
From $413 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 $562 per night (USD)VRBO
The Water's Edge Rental Cambridge, Md - sleeps 10, 4 bedrooms
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our newly renovated 1920s Waterfront bungalow, where there is something for everyone. Looking for a getaway ...
From $562 per night (USD)VRBO
From $561 per night (USD)Expedia
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 $561 per night (USD)Expedia
From $278 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 $278 per night (USD)VRBO
From $874 per night (USD)Expedia
House close to Great Marsh Park and Downtown
- Bedrooms:
- 1
- 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)Expedia
From $1038 per night (USD)VRBO
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 $1038 per night (USD)VRBO
From $570 per night (USD)Expedia
Attractive Waterfront Home over looking Choptank River. Sleeps 5
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This waterfront home has a open floor plan for entertaining and comfortable living. The view of the river is fully visi ...
From $570 per night (USD)Expedia
From $435 per night (USD)VRBO
Stylish Victorian in Historic District
- Bedrooms:
- 3
- 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 $435 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 $102 per night (USD)VRBO
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Wye Mills is waiting for you at this awesome 1-bedroom cottage. With WiFi, heating, a washing machine, and more, guests ...
From $102 per night (USD)VRBO
From $343 per night (USD)Expedia
Waterviews, Comfort & Convenience!
- Bedrooms:
- 2
- 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 $455 per night (USD)VRBO
Walk to Dtwn: Waterfront Eastern Shore Townhome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Game Room | Scenic Waterfront Deck | Community Pool | Pet Friendly w/ Fee | EV Charger Experience life in the heart of ...
From $455 per night (USD)VRBO
From $1156 per night (USD)Expedia
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 $1156 per night (USD)Expedia
From $162 per night (USD)VRBO
Cambridge Apt in Walkable Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Waterfront Setting | Close to Local Eats Explore the quiet side of the Chesapeake Bay with your closest travel buddy at ...
From $162 per night (USD)VRBO
From $358 per night (USD)Expedia
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 $358 per night (USD)Expedia
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 $370 per night (USD)Expedia
Luxury on the river, steps to downtown &boat ramp!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beautifully crafted 1915 Sailmakers home nestled perfectly off the choptank harbor. Newly renovated with stunning appoin ...
From $370 per night (USD)Expedia
From $329 per night (USD)VRBO
New listing! Riverside Retreat on the Choptank River
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dream vacation in the historic city of Cambridge, Maryland! This charming well appointed Riverview renta ...
From $329 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
From $1855 per night (USD)VRBO
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 20
Treat yourself to this unique waterfront retreat where you’ll enjoy stunning ocean liner views of the Choptank River fro ...
From $1855 per night (USD)VRBO
From $754 per night (USD)Expedia
Choptank River Beach Home w/ Pier in Cambridge!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Riverfront Location | In-Unit Washer & Dryer | Gas Grill for Group Cookouts Your next waterfront retreat awaits at thi ...
From $754 per night (USD)Expedia
From $275 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 $275 per night (USD)VRBO
From $358 per night (USD)Expedia
Waterfront, cozy cottage with private pool on 27 acres \n\n\n\n\n\n
- Bedrooms:
- 1
- 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 $358 per night (USD)Expedia
From $272 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 $272 per night (USD)VRBO
From $472 per night (USD)Expedia
Charming 4 bedroom in Historic Cambridge\n\n
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy the old world charm of this home, built in 1894 in the historic district of the picturesque and diverse town of Ca ...
From $472 per night (USD)Expedia
From $398 per night (USD)VRBO
Family friendly with a Pool and Game Room. Convenient Location with a view.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Come stay at this centrally-located home with beautiful views of the Choptank River. Enjoy sun filled days by the custom ...
From $398 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