Chester River Rentals
- From $508 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 $508 per night (USD)VRBO
- From $1350 per night (USD)
Expedia
The Colonial Farmhouse
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to the beautiful Eastern Shore of Maryland and relax at the Colonial Farmhouse. This family-friendly, historic pr ...
From $1350 per night (USD)Expedia
- From $339 per night (USD)
VRBO
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 $339 per night (USD)VRBO
- From $699 per night (USD)
Expedia
Kent Island Luxury Waterfront
- Bedrooms:
- 4
- 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 $699 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Hidden gem with water and golf course views! Bike ride to downtown!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Relax by the fire pit and watch the sun set over the pond and golf course! If you like birdwatching, we have amazing gre ...
From $375 per night (USD)VRBO
- From $700 per night (USD)
Expedia
Spacious, family-friendly home; vast outdoor space on the water w\/ private dock
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
The vacation of your dreams awaits at this bayfront beauty. Large enough for the whole family to enjoy and boasting a da ...
From $700 per night (USD)Expedia
- From $358 per night (USD)
VRBO
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 $358 per night (USD)VRBO
- From $619 per night (USD)
VRBO
River Lodge, Casual Riverfront setting
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The River Lodge sits on the scenic Chester River located 5 miles outside of Chestertown. It's the perfect little get ...
From $619 per night (USD)VRBO
- From $275 per night (USD)
VRBO
In town location with porches and shady patios
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy your time in the quaint town of Rock Hall with its waterfront restaurants and quaint shops. Pirate's Cove is cent ...
From $275 per night (USD)VRBO
- Click For Pricing
Expedia
Historic downtown Chestertown Home. #1 Location.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Your family and guests will experience the best of Chestertown in this family friendly and historic home. 2 Blocks from ...
Click For PricingExpedia
- From $281 per night (USD)
VRBO
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 $281 per night (USD)VRBO
- From $225 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 $225 per night (USD)VRBO
- Click For Pricing
VRBO
Private, Luxury Family Retreat - Corsica River on Maryland's Eastern Shore
- Bedrooms:
- 5
- 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 PricingVRBO
- From $375 per night (USD)
Expedia
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 $375 per night (USD)Expedia
- From $949 per night (USD)
VRBO
Waterfront w\/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Remodeled and Enlarged in 2022. NEW KITCHEN REMODEL for 2024 season. Now Available and Filling Up Fast, "Nauti or Knot ...
From $949 per night (USD)VRBO
- 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 PricingExpedia
- From $110 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 $110 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Waterfront property on 3\/4 acres with private beach, pool, hot tub, and pier.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Sleeps 6. This is a 1450 sq ft, 2-bedroom unit on the ground floor of a two story duplex overlooking the expansive Chest ...
From $375 per night (USD)Expedia
- From $225 per night (USD)
VRBO
The Mellow Yellow Rancher near the Chesapeake Bay.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Great open floor plan with 3 bedrooms and 2 full baths. Sleeps 7 plus full size blow up mattress. Newly renovated and ...
From $225 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Secluded Waterfront Cottage on 200 acre farm near Queenstown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
4bedroom, 2 bathroom, air conditioned house on 200 acre farm with a mile of waterfront on Maryland's Eastern Shore. With ...
From $275 per night (USD)Expedia
- From $275 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 $275 per night (USD)VRBO
- From $198 per night (USD)
Expedia
Entire Townhouse in Rock Hall
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
"Welcome Aboard" to our adorable 3 Bedroom Duplex in a quiet community within walking distance to waterfront marinas and ...
From $198 per night (USD)Expedia
- From $356 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 $356 per night (USD)VRBO
- From $675 per night (USD)
Expedia
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This lovely working farm is on a peninsula situated between Grove Creek and (surely not to your surprise) Reed Creek, wh ...
From $675 per night (USD)Expedia
- From $365 per night (USD)
VRBO
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Chester River Dreams, offers spectacular views of the Chester River from the Family room, Kitchen, & Dining room, Deck, ...
From $365 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Serene Waterfront Cottage with dock and gorgeous views.
- Bedrooms:
- 2
- 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 $325 per night (USD)Expedia
- From $201 per night (USD)
VRBO
Bayside Cottage steps from Rock Hall Harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our charming bayside cottage, just steps away from Rock Hall harbor, Bayside Landing Park, and waterfront res ...
From $201 per night (USD)VRBO
- From $243 per night (USD)
Expedia
Charming Chestertown Waterfront Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your stay in Chestertown in a waterfront home on a tidal creek that is only minutes from historic downtown and Was ...
From $243 per night (USD)Expedia
- From $281 per night (USD)
VRBO
Country Estate in Historic District
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath. Our house ...
From $281 per night (USD)VRBO
- From $1393 per night (USD)
Expedia
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 25
Heated pool, hot tub, boat dock, and sauna! 5 acres of unobstructed Chesapeake Bay views and complete privacy. Surrounde ...
From $1393 per night (USD)Expedia
- From $500 per night (USD)
VRBO
WATERFRONT right on a BEACH
- Bedrooms:
- 3
- 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 $500 per night (USD)VRBO
- From $252 per night (USD)
Expedia
This is truly a Baydream!
- Bedrooms:
- 3
- 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 $252 per night (USD)Expedia
- From $122 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 $122 per night (USD)VRBO
- From $850 per night (USD)
Expedia
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 $850 per night (USD)Expedia
- From $185 per night (USD)
VRBO
Owl Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
You won’t forget your time in this romantic, memorable treehouse. A renovated 19th century carriage house, Owl Cottage ...
From $185 per night (USD)VRBO
- From $777 per night (USD)
Expedia
Sprawling Waterfront Home, Dock & In-Home Theatre
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Winchester Creek Estate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $777 per night (USD)Expedia
- From $424 per night (USD)
VRBO
Serenity on the Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Come relax and enjoy the peaceful water views and serene nature at this newly constructed 2 bedroom oasis in Kent Island ...
From $424 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Belle Blu of Kent Narrows Grasonville, Maryland
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a stylish experience at this centrally-located place in Grasonville, Maryland of Kent Narrows. Feature 1200 squar ...
From $450 per night (USD)Expedia
- From $2520 per night (USD)
VRBO
Beautiful Waterfront Estate
- Bedrooms:
- 9
- Bathrooms:
- 11
- Sleeps:
- 30
Brittland Manor was built in 1938 and sits on 530 riverside acres. When you drive up the long curved lane you are surro ...
From $2520 per night (USD)VRBO
- From $416 per night (USD)
VRBO
SHH! A quiet family home in Rock Hall
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Please come and enjoy all that the eastern shore of Maryland has to offer in Rock Hall while staying in our 3 bedroom 2. ...
From $416 per night (USD)VRBO
- From $235 per night (USD)
VRBO
Chestertown's Pet-Friendly Little Red Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our darling, historic cottage, recently featured on Chestertown's Historic House Tour, is comfortable, pet-friendly and ...
From $235 per night (USD)VRBO
- From $704 per night (USD)
Expedia
5 acre estate with deep water dock and 1,700 feet of shoreline
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Over 4,500 square foot home with five bedrooms (Plus two sleeping lofts for kids), three baths, expansive screened-in po ...
From $704 per night (USD)Expedia
- From $358 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 $358 per night (USD)VRBO
- From $433 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 $433 per night (USD)VRBO
- From $920 per night (USD)
VRBO
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
This breathtaking property, located on 12 acres, is perfect for a vacation rental, weekend getaway, wedding venue, event ...
From $920 per night (USD)VRBO
- From $125 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 $125 per night (USD)VRBO
- From $299 per night (USD)
VRBO
5 bedroom Historic Victorian by Chester River
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Built in1914 this historic Victorian offers huge wrap around porch. Hardwood floors, vintage Heartland Stove, Antiques, ...
From $299 per night (USD)VRBO
- From $1221 per night (USD)
Expedia
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
- Bedrooms:
- 7
- 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 $1221 per night (USD)Expedia
- From $165 per night (USD)
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 ...
From $165 per night (USD)VRBO
- From $1000 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 $1000 per night (USD)Expedia
- From $450 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 $450 per night (USD)VRBO
- From $710 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 $710 per night (USD)Expedia
- From $290 per night (USD)
VRBO
The Lodge on Main Street, a Victorian Apartment, walk to everything!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Large 2 story Apartment with 3 Bedrooms & 2 Baths, (Sleeps 6-8) Well-maintained Victorian Home in the center of Rock Ha ...
From $290 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Walk or bike to everything in Rock Hall! Well-maintained Victorian Home in the center of Rock Hall. The recently renova ...
From $180 per night (USD)VRBO
- Click For Pricing
VRBO
Come explore Maryland's Eastern Shore. Near Annapolis, Wash. D.C. and Baltimore
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful A frame chalet on Kent Island. Open concept, spacious bedrooms, multiple decks and fenced in back yard. A shor ...
Click For PricingVRBO
- From $848 per night (USD)
VRBO
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 26
Spacious, comfortable vacation home located on Love Point, the northern tip of Kent Island, in the heart of the upper Ch ...
From $848 per night (USD)VRBO
- From $284 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 $284 per night (USD)VRBO
- From $143 per night (USD)
VRBO
2 Beds, 2.5 Baths, Perfect Downtown Location
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Quaint and charming, our home away from home in historic Chestertown features 2 bedrooms and 2.5 bathrooms and can accom ...
From $143 per night (USD)VRBO
- From $1400 per night (USD)
VRBO
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
- Bedrooms:
- 7
- 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 $1400 per night (USD)VRBO
- From $635 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 $635 per night (USD)Expedia
- From $300 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 $300 per night (USD)VRBO
- From $449 per night (USD)
Expedia
Harbor View Haven | Waterfront w\/ Dock + HOT TUB!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
BNB Breeze Presents Harbor View Haven! This exquisite waterfront property offers a captivating retreat to relax and rec ...
From $449 per night (USD)Expedia
- From $175 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 $175 per night (USD)VRBO
- From $419 per night (USD)
Expedia
Waterfront Millington Vacation Rental w\/ Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 10
Book a tranquil East Coast getaway at this 60-acre vacation rental in Millington, MD. This secluded waterfront property ...
From $419 per night (USD)Expedia
- From $237 per night (USD)
VRBO
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
- Bedrooms:
- 3
- 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 $237 per night (USD)VRBO
- From $208 per night (USD)
Expedia
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
- Bedrooms:
- 3
- 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 $208 per night (USD)Expedia
- From $281 per night (USD)
VRBO
Waterfront at \"The Landing\" in Historic Rock Hall, overlooking marina and pool.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Landing, the heart of rock hall The expansive open water views of the Harbor and beyond will nourish the soul. Your ...
From $281 per night (USD)VRBO
- From $229 per night (USD)
Expedia
Private, cozy guest house with luxury king suite
- 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 $229 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $150 per night (USD)
Expedia
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 $150 per night (USD)Expedia
- From $239 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 $239 per night (USD)VRBO
- From $964 per night (USD)
Expedia
Waterfront family resort Lodge with private pier, game room and bar
- Bedrooms:
- 4
- 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 $964 per night (USD)Expedia
- From $675 per night (USD)
VRBO
Historic Stepne Manor on Maryland's Eastern Shore
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Accommodations: Manor House - Five Bedrooms (including one Private Suite), three and one-half Baths, Sitting Room, Den, ...
From $675 per night (USD)VRBO
- From $217 per night (USD)
Expedia
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 $217 per night (USD)Expedia
- From $267 per night (USD)
VRBO
Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay
- Bedrooms:
- 2
- 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 $267 per night (USD)VRBO
- From $160 per night (USD)
Expedia
Historic Downtown Garden Oasis with Private Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesth ...
From $160 per night (USD)Expedia
- From $190 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 $190 per night (USD)VRBO
- From $704 per night (USD)
Expedia
Queenstown Waterfront | Boat Ramp | Pool | Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
This 3,600 square foot, 4-bedroom, 3.5-bathroom Wye River waterfront was designed with your comfort in mind, the open fl ...
From $704 per night (USD)Expedia
- From $275 per night (USD)
VRBO
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to the Cottage on N. Main St. Your home away from home located on a quiet street and peaceful at night. This 3 ...
From $275 per night (USD)VRBO
- From $800 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 $800 per night (USD)Expedia
- From $392 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 $392 per night (USD)VRBO
- From $790 per night (USD)
Expedia
Private pier and pool at this waterfront Chestertown home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
This private waterfront river home in beautiful historic Chestertown has its own private pier and pool - all on a quiet ...
From $790 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Waterfront venue on secluded 60 acres with 2 homes great for a family retreat
- Bedrooms:
- 3
- 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 $400 per night (USD)VRBO
- From $360 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 $360 per night (USD)Expedia
- From $206 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 $206 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
You can explore the Eastern Shore's cuisine within a 5 minute drive to Kent Narrows. Enjoy a relaxing fishing trip with ...
From $175 per night (USD)Expedia
- From $195 per night (USD)
VRBO
Coastal Kent Narrows Home on Bay\n\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this newly renovated home on Kent Island! This place is located right in the heart of the action and is walki ...
From $195 per night (USD)VRBO
- From $3235 per night (USD)
Expedia
Exquisite 14,000 sq ft Waterfront Mansion with Pool
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Indulge in splendor at this sprawling 14,000-square-foot waterfront villa, spread out over 15 acres of Bayfront shorelin ...
From $3235 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Chic&Cozy Chesapeake Home with a ship's bar in the charming town of Rock Hall 🦀
- Bedrooms:
- 3
- 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 $350 per night (USD)VRBO
- Click For Pricing
VRBO
Loft at Fountain Park - Prime Downtown Location\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Perhaps the best apartment in Chestertown. This unique residence blends old-world charm with contemporary luxury and boa ...
Click For PricingVRBO
- From $467 per night (USD)
VRBO
Beautiful Chesapeake Bay Views -pet friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Maryland’s Chesapeake bay is an ever changing panorama of spectacular sunsets, teeming wildlife, graceful sailboats, and ...
From $467 per night (USD)VRBO
- From $2000 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 $2000 per night (USD)Expedia
- From $643 per night (USD)
VRBO
Victorian Hideaway: Beautiful Exterior, Modern interior
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet ...
From $643 per night (USD)VRBO
- From $642 per night (USD)
Expedia
Langford Creek Estate | Waterfront w\/ HOT TUB + Deck!
- Bedrooms:
- 3
- 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 $642 per night (USD)Expedia
- From $775 per night (USD)
VRBO
Breathtaking waterfront home on the Chester River
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Private, one-of-a-kind waterfront home on the Chester River minutes from historic Chestertown. Drive through a gated ent ...
From $775 per night (USD)VRBO
- From $260 per night (USD)
VRBO
Water View from Front yard, 3 min walk to the Bay, restaurants and shopping
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Quaint , single-family home , newly renovated and within a 3 min. walk to the popular restaurants/marina and shopping. ...
From $260 per night (USD)VRBO
- From $550 per night (USD)
VRBO
The Lazy River House
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to this freshly renovated, waterfront home on the Chester River. Gorgeous sunsets, picturesque views of the Rive ...
From $550 per night (USD)VRBO
- From $750 per night (USD)
Expedia
Great waterfront house in Grasonville
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Modern Contemporary waterfront house with grand kitchen open floor plan 3 levels overlooking Bay on Eastern shore just m ...
From $750 per night (USD)Expedia