Chester River, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Chester River, Maryland on RentalSaver.com!

Chester River Rentals

From $583 per night (USD)
VRBO
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
My place is located in a quaint neighborhood close to downtown Chestertown; 1 mile walk. This home has a large screened ...
From $583 per night (USD)
VRBO
From $1152 per night (USD)
Expedia
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)
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 $396 per night (USD)
Expedia
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Remodeled in 2023, this light-filled, 2-story private home offers 2,100 sqft of stylish comfort—perfect for a relaxing g ...
From $396 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 $1461 per night (USD)
Expedia
The Colonial Farmhouse
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Escape to the beautiful Eastern Shore of Maryland and relax at the Colonial Farmhouse. This family-friendly, historic pr ...
From $1461 per night (USD)
Expedia
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 $383 per night (USD)
Expedia
Kent Island Waterfront Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private 2 bedroom 1 bathroom waterfront cottage on the Chester River. Enjoy the solitude that this property offers, incl ...
From $383 per night (USD)
Expedia
From $804 per night (USD)
VRBO
Kent Island Luxury Waterfront
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Get away from the city and enjoy the waterfront views from the property that is nestled down a private road. Perfect for ...
From $804 per night (USD)
VRBO
From $366 per night (USD)
Expedia
River Front, Private Single Family Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Soak in the waterfront hot tub or sit around the fire pit in this one story completely renovated house with 3 bedrooms a ...
From $366 per night (USD)
Expedia
From $633 per night (USD)
VRBO
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Recently updated 4 bedroom home in a centralized, quiet, location with no shortage of amazing views of the Chesapeake Ba ...
From $633 per night (USD)
VRBO
From $288 per night (USD)
Expedia
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)
Expedia
From $873 per night (USD)
VRBO
Sprawling Waterfront Home with views, Dock and In-Home Theatre
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Winchester Creek Estate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $873 per night (USD)
VRBO
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
Click For Pricing
Expedia
Private, Luxury Family Retreat - Corsica River on Maryland's Eastern Shore
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Gray Fox Farm is a 135-acre, classic Chesapeake Bay-style estate located on the scenic (and largely undiscovered) Corsi ...
Click For Pricing
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
From $337 per night (USD)
VRBO
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)
VRBO
From $196 per night (USD)
Expedia
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)
Expedia
From $199 per night (USD)
VRBO
Cass-Away Luxury Houseboat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Kent Narrows Rentals welcomes you aboard Cass-Away. A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a ...
From $199 per night (USD)
VRBO
From $779 per night (USD)
Expedia
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Working Farm on Reeds Creek This lovely working farm is on a peninsula situated between Grove Creek and (surely not to ...
From $779 per night (USD)
Expedia
From $515 per night (USD)
VRBO
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)
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 $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 $401 per night (USD)
Expedia
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)
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 $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 $238 per night (USD)
Expedia
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4bedroom, 2 bathroom, air conditioned house on 200 acre farm with a mile of waterfront on Maryland's Eastern Shore. With ...
From $238 per night (USD)
Expedia
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
Click For Pricing
Expedia
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 Pricing
Expedia
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 $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 $649 per night (USD)
VRBO
NEW Spacious 5BDR house on serene Kent Island - close to all the hot spots!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to your serene escape on the beautiful shores of Love Point in Stevensville, MD! This spacious 5-bedroom, 3.5-b ...
From $649 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 $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 $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 $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 $944 per night (USD)
VRBO
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)
VRBO
From $152 per night (USD)
VRBO
Eastern Shore Get Away
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Located on Maryland's Eastern Shore, on the Chester River, this fully furnished 1 bedroom, 1 bathroom apartment has all ...
From $152 per night (USD)
VRBO
From $343 per night (USD)
VRBO
5 bedroom Historic Victorian by Chester River
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Built in1914 this historic Victorian offers huge wrap around porch. Hardwood floors, vintage Heartland Stove, Antiques, ...
From $343 per night (USD)
VRBO
From $1223 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
Relax on the Eastern Shore of Kent Narrows in a King Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Spacious vacation rental with king sized bed and all the comforts of home. Large kitchen and living room. Queen sized sl ...
Click For Pricing
VRBO
From $1120 per night (USD)
Expedia
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)
Expedia
From $527 per night (USD)
VRBO
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire t ...
From $527 per night (USD)
VRBO
Click For Pricing
Expedia
Belle Blu of Kent Narrows Grasonville, Maryland
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
<p>You'll find bicycles on site at this family-friendly apartment. With convenient onsite parking, you'll be ready to ma ...
Click For Pricing
Expedia
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 $563 per night (USD)
Expedia
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Bedrooms:
3
Bathrooms:
5
Sleeps:
25
Spacious, comfortable vacation home located on Love Point, the northern tip of Kent Island, in the heart of the upper Ch ...
From $563 per night (USD)
Expedia
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 $1192 per night (USD)
Expedia
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Bedrooms:
6
Bathrooms:
5
Sleeps:
16
Set on 6 acres overlooking the beautiful Corsica River amidst idyllic farms, your home away from home calls. A 5-bedroom ...
From $1192 per night (USD)
Expedia
From $757 per night (USD)
VRBO
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)
VRBO
From $326 per night (USD)
Expedia
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)
Expedia
From $456 per night (USD)
VRBO
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recha ...
From $456 per night (USD)
VRBO
From $804 per night (USD)
Expedia
Private Peaceful Waterfront House with Pool & Hot Tub
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Family owned beautiful waterfront home with a fully stocked kitchen, dining room, master bedroom and large living areas. ...
From $804 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
“Old Bridge” is a 100-year-old house in a quiet Kingstown section of Chestertown. The house is an "American Four Square" ...
From $241 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 $445 per night (USD)
VRBO
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
A nature lovers dream! Kick back and relax in this tranquil, cozy space, with picture perfect sunsets, surrounded by nat ...
From $445 per night (USD)
VRBO
From $520 per night (USD)
VRBO
Waterfront Millington Vacation Rental w/ Hot Tub!
Bedrooms:
4
Bathrooms:
7
Sleeps:
10
Book a tranquil East Coast getaway at this 60-acre vacation rental in Millington, MD. This secluded waterfront property ...
From $520 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 $254 per night (USD)
Expedia
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy the peace and tranquility at "Outrange," Blue Heron Farm's recently updated cabin. While we are new to VRBO, we h ...
From $254 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Blue Heron Farm Waterfront Chalet
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of ...
From $344 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 $688 per night (USD)
Expedia
Pet-Friendly Home on Chester River w/ Dock!
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Seasonal Outdoor Pool (May 15-September 15) | Kayaks & Canoe Provided | Crab Traps Calling all waterfront explorers! Lo ...
From $688 per night (USD)
Expedia
$Victorian Lodge on Main Street, Rock Hall MD\nWalk to Everything!!!\nSleeps 2 to 4$
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 $392 per night (USD)
VRBO
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)
VRBO
From $555 per night (USD)
Expedia
Welcome to the secluded waterfront oasis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The cottage has lovely water views from the full kitchen, living room, and a stunning luxurious first floor master suite ...
From $555 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 $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 $558 per night (USD)
VRBO
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)
VRBO
From $344 per night (USD)
Expedia
Waterfront condo. Completely renovated. Walk to Kent Island's best places
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Invited to a Kent Island wedding or event -- going to a boat show or Navy football game? This waterfront condo is the pe ...
From $344 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
Click For Pricing
Expedia
Renovated Rancher on Kent Island near Chesapeake Bay Bridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Cozy yet modern rancher equipped with 3 bedrooms, 2 baths, and spacious open floor plan! Whether you’re looking to be cl ...
Click For Pricing
Expedia
From $271 per night (USD)
VRBO
Cass-N-Reel Luxury Houseboat
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With one bedroom, on ...
From $271 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 $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 $985 per night (USD)
Expedia
Waterfront Estate w Private Pier, Game Room & Bar
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
Welcome to the waterfront Twin Ponds Lodge, built in 1987 and for many of its years was used as overnight accommodations ...
From $985 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Cozy, unique, historic registered cottage on the Corsica River!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Captains Quarters was built in 1880 by local waterman, Captain John H. Osman. The Captain built 4 identical houses f ...
From $196 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 $861 per night (USD)
VRBO
Queenstown Waterfront | Boat Ramp | Pool | Private Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Ideal felicity and perfection! This 3,600 square foot, 4-bedroom, 3.5-bathroom Wye River waterfront was designed with y ...
From $861 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 $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 $450 per night (USD)
VRBO
Waterfront venue on secluded 60 acres with 2 homes great for a family retreat
Bedrooms:
4
Bathrooms:
7
Sleeps:
8
Relax with the whole family at this peaceful secluded property. Located on the Chester River in Millington, MD, Pine For ...
From $450 per night (USD)
VRBO
From $456 per night (USD)
Expedia
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our charming Chestertown Home! This beautiful house offers a comfortable and inviting space for your stay. W ...
From $456 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape to this stylish, private, waterfront home. Fish or kayak off a private dock on the Chester River and enjoy the vi ...
From $245 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You can explore the Eastern Shore's cuisine within a 5 minute drive to Kent Narrows. Enjoy a relaxing fishing trip with ...
From $412 per night (USD)
Expedia
From $457 per night (USD)
VRBO
Grasonville Home w/ Private Pool on the Water
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Become enveloped by Maryland hospitality when you stay at ‘The Winchester,’ a gorgeous home right on the water. With stu ...
From $457 per night (USD)
VRBO
From $830 per night (USD)
Expedia
Waterfront 4 BR home with private pier and boat dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The waterfront house has 4BR and 4BA with 3900 sq ft + a two car garage. It has the benefits of both protected water fo ...
From $830 per night (USD)
Expedia
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
From $389 per night (USD)
Expedia
Historic luxury townhouse in the heart of downtown Chestertown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Historic Luxury Townhouse on High Street – Heart of Downtown Chestertown Welcome to 125 High Street—an exquisitely reno ...
From $389 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
• Embrace historic charm in our exquisitely renovated third-floor walk-up, located in a beautiful historic building in t ...
From $313 per night (USD)
VRBO
From $1099 per night (USD)
Expedia
Blake House Historic Estate with Private Inn
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Summary: Blake House represents one of the oldest colonial homes in Maryland, built by British settler, Charles Blake, o ...
From $1099 per night (USD)
Expedia
From $749 per night (USD)
VRBO
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
BNB Breeze Presents: Langford Estates! Step into your very own, secluded 790-acre sanctuary! This 1864 home has been new ...
From $749 per night (USD)
VRBO
From $705 per night (USD)
VRBO
Victorian Hideaway: Beautiful Exterior, Modern interior
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet ...
From $705 per night (USD)
VRBO

Search Your Destination Now!

Chester River Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 105 Rentals