Kent Area Rentals
From $355 per night (USD)VRBO
Bayside Cottage steps from Rock Hall Harbor
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our charming bayside cottage, just steps away from Rock Hall harbor, Bayside Landing Park, and waterfront res ...
From $355 per night (USD)VRBO
From $258 per night (USD)Expedia
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Bayside Breeze, your home away from home! Located only one block from Rock Hall’s very own Ferry Beach, nestl ...
From $258 per night (USD)Expedia
From $401 per night (USD)VRBO
Country Estate in Historic District
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath. Our house ...
From $401 per night (USD)VRBO
From $387 per night (USD)Expedia
Serene Waterfront Cottage with dock and gorgeous views.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 7
Egret's Nest is a charming waterfront cottage located on Gray's Inn Creek with access to the Chesapeake Bay. Drive up a ...
From $387 per night (USD)Expedia
From $159 per night (USD)VRBO
First Floor Studio Apartment in Historic Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everyt ...
From $159 per night (USD)VRBO
From $1746 per night (USD)Expedia
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 25
Heated pool, hot tub, boat dock, and sauna! 5 acres of unobstructed Chesapeake Bay views and complete privacy. Surrounde ...
From $1746 per night (USD)Expedia
From $333 per night (USD)VRBO
200 steps to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming and spacious two-bedroom, 1 1/2 bath cottage with glimpses of the Chesapeake Bay and very close to the Rock Hal ...
From $333 per night (USD)VRBO
From $604 per night (USD)Expedia
WATERFRONT right on a BEACH
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Sunset at Rabbit Run is perfect for a family or friends enjoying the Chesapeake Bay area with views of the Chesapeake ba ...
From $604 per night (USD)Expedia
From $270 per night (USD)VRBO
This is truly a Baydream!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Baydream is in a quiet community that is centrally located in the quaint historic fishing town of Rock Hall. This 2 bed ...
From $270 per night (USD)VRBO
From $506 per night (USD)Expedia
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Waterfront house sleeps 10 max. With 4-Bedrooms & 2 full Baths. This home is where you'll find breathtaking views. ...
From $506 per night (USD)Expedia
From $198 per night (USD)VRBO
BEACH WITHOUT THE BUSTLE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This condo is situated in the quiet town of Betterton and located just steps away from the largest and most beautiful be ...
From $198 per night (USD)VRBO
From $337 per night (USD)Expedia
Welcome to Mermaid Haven! The perfect spacious home for your Rock Hall vacaction
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
This spacious 3 bdrm, 2 bath home is located in the quaint town of Rock Hall, MD and is within walking distance to downt ...
From $337 per night (USD)Expedia
From $196 per night (USD)VRBO
Entire Townhouse in Rock Hall
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
"Welcome Aboard" to our adorable 3 Bedroom Duplex in a quiet community within walking distance to waterfront marinas and ...
From $196 per night (USD)VRBO
From $515 per night (USD)Expedia
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Chester River Dreams, offers spectacular views of the Chester River from the Family room, 2 bedrooms, Kitchen, & Dining ...
From $515 per night (USD)Expedia
From $386 per night (USD)VRBO
Sailors Crossing
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Sailors Crossing! Your home away from home. Short walk to Main St, harbor and restaurants. Next to tennis and ...
From $386 per night (USD)VRBO
From $649 per night (USD)Expedia
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
NEW KITCHEN REMODEL in 2024. "Nauti or Knot" has been refreshed! Now available and filling up fast. Fabulous waterfron ...
From $649 per night (USD)Expedia
Click For PricingVRBO
Charming 1920's Bungalow Near Water & Amenities
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming and cozy 2 bedroom bungalow. Just a couple of blocks away from the main attractions Rock Hall has to offer incl ...
Click For PricingVRBO
From $329 per night (USD)Expedia
Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic C ...
From $329 per night (USD)Expedia
From $261 per night (USD)VRBO
Overton Farm Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Newly renovated waterfront cottage. Everything in this home is new! We are located next to Eastern Neck National Wildlif ...
From $261 per night (USD)VRBO
From $374 per night (USD)Expedia
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Stunning view overlooking the Chesapeake Bay, and a quick 5 minute stroll to scenic Betterton Beach! This historic wate ...
From $374 per night (USD)Expedia
From $449 per night (USD)VRBO
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Charming, spacious home with modern updates in a lovely town on the Chesapeake Bay. New air conditioning/heating system ...
From $449 per night (USD)VRBO
From $530 per night (USD)Expedia
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This waterfront 4 BR, 2 1/2 BA Private house in the town of Rock Hall has been recently renovated. Its newest addition ...
From $530 per night (USD)Expedia
From $1345 per night (USD)VRBO
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Stunning waterfront property in Rock Hall. Expansive outdoor space with large pool and long pier on picturesque Swan Cre ...
From $1345 per night (USD)VRBO
From $303 per night (USD)Expedia
BAYSIDE BUNGALOW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lovely bayside Bungalow on a quiet street on Swan Creek with an indoor dry Swedish sauna and views of the cheseapeake Ba ...
From $303 per night (USD)Expedia
From $288 per night (USD)VRBO
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
You will be close to everything in Rock Hall when you stay at this centrally-located ground-level apartment. Just 1 bloc ...
From $288 per night (USD)VRBO
From $302 per night (USD)VRBO
Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Just two hours from the Philadelphia or DC metro area, you will find the Bay Beach Oasis. Less than a 5 minute walk to ...
From $302 per night (USD)VRBO
From $267 per night (USD)VRBO
River Cottage, Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Relax on the scenic Eastern Shore. We are located just off the Chester River. Step away from the hustle and bustle to ou ...
From $267 per night (USD)VRBO
From $595 per night (USD)VRBO
8-bedroom house with AC and WiFi in Betterton. 7 minute walk to the beach.
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 14
Built in 1903 as an inn, Price Cottage is now an 8-bed, 4-bath guest house filled with every amenity needed for a unique ...
From $595 per night (USD)VRBO
From $735 per night (USD)VRBO
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Forget your worries in this spacious and serene waterfront property with expansive Privacy and Fabulous water views of t ...
From $735 per night (USD)VRBO
From $170 per night (USD)Expedia
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Bring the whole family to this great historic 1850s duplex with lots of room for fun. There are 4 bedrooms and 2 1/2 bat ...
From $170 per night (USD)Expedia
From $216 per night (USD)VRBO
Charming cottage with Pool Access and WiFi in lovely Rock Hall
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nestled in Rock Hall, this delightful cottage is a perfect retreat for guests. With 1 cozy bedroom, AC, WiFi, and heatin ...
From $216 per night (USD)VRBO
From $316 per night (USD)Expedia
Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Discover this lovely 2 bedroom and loft gem in Chestertown. This welcoming apartment features 3 queen beds, perfect for ...
From $316 per night (USD)Expedia
From $1152 per night (USD)VRBO
A Waterfront Oasis with pier and pool. Spacious 4 bedrooms near Chestertown.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Welcome to Lovely Cove Farm. Close to Chestertown and Rock Hall for shopping and dining, but a world away. Secluded and ...
From $1152 per night (USD)VRBO
From $486 per night (USD)Expedia
Chesapeake Bay Retreat W/Breathtaking Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to serenity on the shores of Chesapeake Bay! This luxurious, multimillion-dollar waterfront retreat offers sweepi ...
From $486 per night (USD)Expedia
From $722 per night (USD)VRBO
Down by the River - Charming house on river & walkable to historic Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Your beautiful retreat in Chestertown awaits! Gorgeous views on the water and walking distance to charming Chestertown. ...
From $722 per night (USD)VRBO
From $498 per night (USD)VRBO
Charming 2-bedroom first floor apartment in Chestertown with Cute Outdoor Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This modern luxury unit boasts a first-floor apartment with two bedrooms, full access to a private back patio/outdoor sp ...
From $498 per night (USD)VRBO
From $619 per night (USD)VRBO
Modern Lux Upstairs apt in Chestertown/Family Friendly/Walk to Shops and Dining!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Experience the charm of Chestertown, Maryland by indulging in a stay at our upscale vacation residence. Located just a s ...
From $619 per night (USD)VRBO
From $338 per night (USD)VRBO
Hydrangea House at Betterton Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our beautifully restored Victorian home nestled in the heart of Betterton, Maryland. Over 100 years old, this ...
From $338 per night (USD)VRBO
From $446 per night (USD)VRBO
Anchors Away!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar exp ...
From $446 per night (USD)VRBO
From $323 per night (USD)VRBO
Walking distance to restaurants and marinas...dog-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Unwind in this charming 3-bedroom dog-friendly home in Rock Hall, just one block off of the harbor and within walking di ...
From $323 per night (USD)VRBO
From $739 per night (USD)VRBO
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Rock Hall, know as the "Pearl of the Chesapeake" is located directly on the Chesapeake Bay, Bay Breeze Inn is located ri ...
From $739 per night (USD)VRBO
From $342 per night (USD)Expedia
Eastern Shore beach cottage get-away
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Recently renovated, charming cottage. A sandy beach is right across the quiet street from the cottage. The sandy botto ...
From $342 per night (USD)Expedia
From $438 per night (USD)VRBO
Stay in the landmark Lighthouse!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
3 BR 3 Bath w/Elevator providing easy access to all 3 floors. Wrap-A-Round 3rd Floor deck providing 360 degree panoramic ...
From $438 per night (USD)VRBO
From $963 per night (USD)Expedia
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Eagle Point Farm located on Maryland's beautiful Eastern Shore, a 90 minute drive from Washington DC, Philade ...
From $963 per night (USD)Expedia
From $1199 per night (USD)VRBO
Historic Manor House on Beautiful Eastern Shore Estate
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
THORNTON Estate, established in 1664, is a quintessential Eastern Shore estate. The magnificent manor house anchors the ...
From $1199 per night (USD)VRBO
From $272 per night (USD)VRBO
Blissful Retreat In Rock Hall
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In the delightful town of Rock Hall lies a snug two-bedroom cottage, ideal for your upcoming getaway. As you step inside ...
From $272 per night (USD)VRBO
From $216 per night (USD)VRBO
Life is better at the RIVER!--Cozy waterfront cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Located in quiet community of Galena, MD, this charming cottage is a river front property a step away from beauty of the ...
From $216 per night (USD)VRBO
From $323 per night (USD)Expedia
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Rock Hall - Voted as one of the 10 best towns in Maryland for many years. There is a Holiday and special event suppleme ...
From $323 per night (USD)Expedia
From $254 per night (USD)VRBO
In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or long term stay. Tastefully updated 2-bedroom, ...
From $254 per night (USD)VRBO
From $450 per night (USD)VRBO
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The privacy of a waterfront home welcomes you to pause and enjoy the beauty of the Chester River. Water views from every ...
From $450 per night (USD)VRBO
From $314 per night (USD)VRBO
Beautiful Retreat Located in Rock Hall - walk to everything!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Sharp Street Retreat is located in the heart of Rock Hall, on the Eastern Shore of the Chesapeake Bay. Home is convenien ...
From $314 per night (USD)VRBO
From $319 per night (USD)Expedia
Contemporary waterfront house with private dock & kayaks!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to tranquility at Mill Creek House, a contemporary waterfront sanctuary just 15 mins from Chestertown. Enjoy suns ...
From $319 per night (USD)Expedia
From $239 per night (USD)VRBO
Peaceful getaway convenient to local amenities including beach, boating & food
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bay Haven Cottage---Comfortable redecorated cottage with lots of amenities featuring all new beachy decor with open floo ...
From $239 per night (USD)VRBO
From $1044 per night (USD)VRBO
Luxurious Home on the Chesapeake Bay, Fantastic Views, W/ Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy this spacious 2800 sq. ft. private home situated on 19 acres that has 1500 feet of bay front on the Chesapeake Bay ...
From $1044 per night (USD)VRBO
From $1120 per night (USD)VRBO
Sunset Lodge on the Bay
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
A waterfront estate set apart from the rest, offering something unique that’s hard to find on Maryland’s eastern shore. ...
From $1120 per night (USD)VRBO
From $250 per night (USD)VRBO
Brand New Cottage Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Bayside Beach House was named House of the Week! Check it out: Professionally built vacation rental with charm and com ...
From $250 per night (USD)VRBO
From $1223 per night (USD)VRBO
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Riverfront Retreat, a beautiful and spacious home where your family will be able to relax and enjoy the best ...
From $1223 per night (USD)VRBO
From $944 per night (USD)Expedia
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
This breathtaking property, located on 12 acres, is perfect for a vacation rental, weekend getaway, wedding venue, event ...
From $944 per night (USD)Expedia
From $331 per night (USD)VRBO
EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 11
EASTERN SHORE OF MARYLAND on the Chesapeake Bay in the historic town of Betterton, Maryland, your day begins with coffee ...
From $331 per night (USD)VRBO
From $171 per night (USD)VRBO
Carriage House Hideaway in Middle of Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens ...
From $171 per night (USD)VRBO
From $298 per night (USD)VRBO
Newly restored apartment in the heart of Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of al ...
From $298 per night (USD)VRBO
From $757 per night (USD)Expedia
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
A waterfront house perfect for a family or friends get away. Large waterview sunroom to watch the activities on the wat ...
From $757 per night (USD)Expedia
From $326 per night (USD)VRBO
Church Creek Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This cottage is newly built on Eastern Neck Island in Rock Hall, Maryland near Eastern Neck Wildlife Refuge. The cottage ...
From $326 per night (USD)VRBO
From $392 per night (USD)Expedia
Sparkling new! A Craftsman-style cottage in the heart of Rock Hall
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestle into this fresh new craftsman-style cottage when you visit Rock Hall. This is the perfect weekend getaway setup f ...
From $392 per night (USD)Expedia
From $269 per night (USD)VRBO
Victorian Lodge on Main Street, Rock Hall MD\nWalk to Everything!!!\nSleeps 2 to 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Walk or bike to everything in Rock Hall! Well-maintained Victorian Home in the center of Rock Hall. The recently renovat ...
From $269 per night (USD)VRBO
From $327 per night (USD)VRBO
The Lodge on Main. A Victorian home. Walk/bike to everything!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Well-maintained Victorian Home in the center of Rock Hall. The recently renovated space on the second and third floors ...
From $327 per night (USD)VRBO
From $125 per night (USD)VRBO
Guest Suite for up to 2 in a Victorian on the Chester River
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our lovingly-restored Millington Manor is the original home of the local doctor, built in 1868. Our small town has a liq ...
From $125 per night (USD)VRBO
From $304 per night (USD)Expedia
Waterfront in Historic Rock Hall, overlooking the main harbor and Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The expansive open water views will nourish the soul. Your spacious townhome is within walking distance of marinas, rest ...
From $304 per night (USD)Expedia
From $365 per night (USD)VRBO
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
At the Tipsea Crab, take a break from the hectic pace of everyday life and visit the town of Rock Hall on the Chesapeake ...
From $365 per night (USD)VRBO
From $305 per night (USD)Expedia
Waterfront Retreat with Private Dock and Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Waterfront Studio Apartment located on the Eastern Shore of Kent County Maryland. Perfect private getaway located on St ...
From $305 per night (USD)Expedia
Click For PricingVRBO
Your perfect Maryland escape awaits!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the serenity at our 3-bedroom retreat that was recently renovated, Immerse yourself in comfort and style with t ...
Click For PricingVRBO
From $289 per night (USD)Expedia
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We are pleased to welcome you to enjoy our newly established home away from home! Whether you are a family or a couple, ...
From $289 per night (USD)Expedia
From $419 per night (USD)VRBO
Eastern shore beachfront cottage with stunning sunset views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Come relax on Chesapeake Bay's Eastern Shore in our updated 3 bedroom cottage. Located in the quiet countryside you'll h ...
From $419 per night (USD)VRBO
From $411 per night (USD)Expedia
Grandma’s Cottage will wrap around you like a warm hug
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This brilliant cottage in Betterton offers a cozy retreat for 4 guests. With 2 charming twin bedrooms, a well-equipped b ...
From $411 per night (USD)Expedia
From $269 per night (USD)VRBO
Charming 3-bedroom house in the Heart of Rock Hall with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful and cozy 3 bedroom (one queen, two kings) with a main floor master, 2 bathroom home centrally located in the h ...
From $269 per night (USD)VRBO
From $558 per night (USD)Expedia
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This newly renovated historic home leaves nothing to be desired. Between the beautiful decor, amenities, and location th ...
From $558 per night (USD)Expedia
From $897 per night (USD)VRBO
Grays Inn Creek Waterfront Pvt. Dock Kayaks & View
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 18
Summary: Recently renovated, this spacious home features 7 bedrooms and 5.5 bathrooms, comfortably sleeping 18 guests. E ...
From $897 per night (USD)VRBO
From $389 per night (USD)Expedia
Waterfront! Private Dock, Boat Tie-Up & Near Town
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Unwind with family or friends at this perfect waterfront getaway. This spacious home features a large sunroom w ...
From $389 per night (USD)Expedia
From $388 per night (USD)VRBO
Heron Cove, a Waterfront vacation spot near Rock Hall with private pier
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your private waterfront retreat in Rock Hall, Maryland! Nestled along the serene shores of the Greys Inn Cree ...
From $388 per night (USD)VRBO
From $840 per night (USD)VRBO
Chesapeake Bay Estate; House and Guesthouse, Beach and Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
House and Guest House with bayfront heated in-ground swimming pool -perfect for 2 families or extended family gatherings ...
From $840 per night (USD)VRBO
From $351 per night (USD)VRBO
Brand New Modern Rock Hall home with Water Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Brand new, custom built home featuring a wall of windows with water views of The Haven on Swan Creek. 3 bedrooms, 3 full ...
From $351 per night (USD)VRBO
From $314 per night (USD)Expedia
Newly renovated single family home with attached guest suite
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Located on the Eastern Shore near Betterton Beach. Come enjoy what this 5-bedroom house has to offer. Guests will have p ...
From $314 per night (USD)Expedia
From $1042 per night (USD)VRBO
Spacious luxury home in charming Downtown Chestertown/Pets Welcome/Free Wifi
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Experience the charm of Chestertown, Maryland by indulging in a stay at our upscale vacation residence. Located just a s ...
From $1042 per night (USD)VRBO
From $253 per night (USD)VRBO
STONE RIVERSIDE COTTAGE is just a few steps from the SASSAFRAS RIVERS edge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one of a kind spot is located on the beautiful Sassafras River. Tranquility mixed with nature at its best on the Ea ...
From $253 per night (USD)VRBO
From $271 per night (USD)VRBO
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Oyster Cottage is a great destination to enjoy the Chesapeake Bay and Maryland's Eastern Shore! We are just a quick walk ...
From $271 per night (USD)VRBO
From $596 per night (USD)VRBO
Escape to Goose Landing: Your Waterfront Retreat in Chestertown!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Goose Landing, our serene waterfront haven nestled on over three acres along the beautiful Fairlee Creek. We' ...
From $596 per night (USD)VRBO
From $191 per night (USD)VRBO
Cottage within walking distance to the Bay!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Down a half mile lane, surrounded by woods and farm land. This property is located between Chestertown and Rock Hall, M ...
From $191 per night (USD)VRBO
From $324 per night (USD)Expedia
Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Great front porch with rocking chairs, lighting, and fans to sit and relax, screened-in back porch, fire pit, picnic tab ...
From $324 per night (USD)Expedia
From $201 per night (USD)VRBO
Peaceful country home away in the wilderness
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relaxed 3 bedroom 2 bath moblie home on 7 acres so peaceful and quiet surrounded by state hunting lands .Listen to the o ...
From $201 per night (USD)VRBO
From $188 per night (USD)Expedia
Historic Downtown Garden Oasis with Private Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesth ...
From $188 per night (USD)Expedia
From $241 per night (USD)VRBO
Knot's Landing, spacious Apt. downtown Rock Hall
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Knot's landing - a spacious apartment located above one of Rock Hall's favorite shops in the quaint Main Stre ...
From $241 per night (USD)VRBO
From $380 per night (USD)VRBO
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Modern cottage on tranquil large grounds on 20 acres with a pond on one end and a half mile wide creek 800 feet away on ...
From $380 per night (USD)VRBO
From $355 per night (USD)VRBO
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Easy walk to everything in Rock Hall - The beach, the marinas, restaurants, bars and shops. 15 minute drive to historic ...
From $355 per night (USD)VRBO
From $624 per night (USD)Expedia
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
This home was originally built in 1830 and has been completely restored lovingly by its owners, and sits upon an overloo ...
From $624 per night (USD)Expedia
From $300 per night (USD)VRBO
Be persuaded to experience this vintage cottage by the Sassa
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Gregg Neck Cottage is a single family home with four bedrooms, a spacious living area, screened-in porch, fully equipped ...
From $300 per night (USD)VRBO
From $226 per night (USD)Expedia
Cute waterfront apartment -- 8 min from the beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
An adorable carriage house with panoramic views overlooking Swan Creek, located on a private road. Nature lovers and bir ...
From $226 per night (USD)Expedia
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Family-Friendly Cottage, Walk to the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Make your days as enjoyable as possible with this versatile and child-proofed vacation rental! Fully equipped with kayak ...
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From $398 per night (USD)VRBO
Chic&Cozy Chesapeake Home with a ship's bar in the charming town of Rock Hall 🦀
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming, comfy home with it's own cantina! This lovely home is set in the picturesque, friendly historic town of Rock H ...
From $398 per night (USD)VRBO
From $545 per night (USD)VRBO
Countryside Cottage in Sassafras
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Sassafras Lodge welcomes groups to a quaint country setting in the Sassafras River watershed. The lodge is situated ...
From $545 per night (USD)VRBO
From $277 per night (USD)VRBO
Rock Hall Retreat w/ Balcony Near Park & Marina!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience comfort and tranquility at this 3-bedroom, 2.5-bath vacation rental in Rock Hall, MD! Perfect for families, t ...
From $277 per night (USD)VRBO