Kent Area Rentals
- From $325 per night (USD)
VRBO
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)VRBO
- From $1160 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 $1160 per night (USD)Expedia
- From $276 per night (USD)
VRBO
Rock N' Reel - near the beach, restaurants, and marinas.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Near the beach, restaurants, and marinas, this newer craftsman home has solid brick exterior and a warm, comfy-feel insi ...
From $276 per night (USD)VRBO
- From $201 per night (USD)
Expedia
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)Expedia
- From $300 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 $300 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 $875 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 $875 per night (USD)VRBO
- From $263 per night (USD)
VRBO
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 $263 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 $264 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 $264 per night (USD)VRBO
- From $790 per night (USD)
Expedia
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 $790 per night (USD)Expedia
- From $800 per night (USD)
VRBO
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 $800 per night (USD)VRBO
- From $98 per night (USD)
Expedia
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 $98 per night (USD)Expedia
- From $230 per night (USD)
VRBO
Brand New Cottage Steps from the Beach!
- Bedrooms:
- 2
- 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 $230 per night (USD)VRBO
- 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 $867 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 $867 per night (USD)VRBO
- From $1491 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 $1491 per night (USD)Expedia
- 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 $627 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 $627 per night (USD)Expedia
- From $211 per night (USD)
VRBO
Peaceful getaway convenient to local amenities including beach, boating & food
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bay Haven Cottage---Comfortable redecorated cottage with lots of amenities featuring all new beachy decor with open floo ...
From $211 per night (USD)VRBO
- From $287 per night (USD)
Expedia
200 steps to the beach!
- Bedrooms:
- 2
- 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 $287 per night (USD)Expedia
- From $350 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 $350 per night (USD)VRBO
- From $280 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 $280 per night (USD)VRBO
- From $270 per night (USD)
VRBO
Contemporary waterfront house with private dock & kayaks!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to tranquility at Mill Creek House, a contemporary waterfront sanctuary just 15 mins from Chestertown. Enjoy suns ...
From $270 per night (USD)VRBO
- From $500 per night (USD)
Expedia
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)Expedia
- From $252 per night (USD)
VRBO
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)VRBO
- 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 $270 per night (USD)
VRBO
BEAUTIFUL BAY FRONT VIEW
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Betterton Beach, “Jewel” of the Chesapeake, Eastern Shore of Maryland on the Chesapeake Bay. Spacious second ...
From $270 per night (USD)VRBO
- From $300 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 $300 per night (USD)VRBO
- From $260 per night (USD)
VRBO
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. VRBO is now collecting sales tax called Lodgi ...
From $260 per night (USD)VRBO
- From $205 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 $205 per night (USD)VRBO
- From $395 per night (USD)
VRBO
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Waterfront house is 2100 square foot, 4-Bedrooms & 2-Baths where you'll find breathtaking views. It is a great plac ...
From $395 per night (USD)VRBO
- From $204 per night (USD)
Expedia
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 $204 per night (USD)Expedia
- Click For Pricing
VRBO
River Retreat | Private Dock, Deck, Grill, Games & Nature
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax and enjoy a peaceful stay on the Sassafras River surrounded by nature. Watch the sunrise from the gorgeous wrap-ar ...
Click For PricingVRBO
- From $225 per night (USD)
Expedia
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)Expedia
- From $400 per night (USD)
VRBO
Unobstructed view of the Chesapeake Bay, w\/ a beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Uniquely situated on a rare and expansive sandy beach on the northern Chesapeake Bay, this bay front dream boasts 2 larg ...
From $400 per night (USD)VRBO
- From $255 per night (USD)
Expedia
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 $255 per night (USD)Expedia
- From $220 per night (USD)
VRBO
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 $220 per night (USD)VRBO
- From $389 per night (USD)
Expedia
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 $389 per night (USD)Expedia
- From $193 per night (USD)
VRBO
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 ...
From $193 per night (USD)VRBO
- From $595 per night (USD)
Expedia
Rambling Victorian Beach House on Maryland's Eastern Shore
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 16
Welcome to Price Cottage in the quaint bayside village of Betterton, MD! Built in 1903 as an inn, this spacious home is ...
From $595 per night (USD)Expedia
- Click For Pricing
VRBO
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 $650 per night (USD)
VRBO
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 $650 per night (USD)VRBO
- From $279 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 $279 per night (USD)VRBO
- From $208 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 $208 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Riverfront Country House on The Sassafras River
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This home has been completely restored lovingly by its owners, and sits upon an overlook of the river. Nature is all aro ...
From $500 per night (USD)VRBO
- From $416 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 $416 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 $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 $1140 per night (USD)
VRBO
Historic Manor House on Beautiful Eastern Shore Estate
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 13
***All New Mattresses installed March 2022*** THORNTON Estate, established in 1664, is a quintessential Eastern Shore e ...
From $1140 per night (USD)VRBO
- From $229 per night (USD)
VRBO
Blissful Retreat In Rock Hall
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This quiet serene home is situated on the Swan Creek. It is peaceful, quiet yet one mile into Rock Hall town and 10 mile ...
From $229 per night (USD)VRBO
- From $711 per night (USD)
VRBO
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 $711 per night (USD)VRBO
- From $185 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 $185 per night (USD)VRBO
- From $375 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 $375 per night (USD)VRBO
- From $699 per night (USD)
Expedia
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 $699 per night (USD)Expedia
- From $292 per night (USD)
VRBO
Dog-Friendly Beach House with Kayaks, Marina & Dive Bar Weekend Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy this oceanfront community at this 2000 sq ft Cape Code Home 4 bedrooms, 2.5 bathrooms with a bonus room with offic ...
From $292 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Spacious Victorian close to everything in RH - Wheelchair friendly.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Easy walk to everything in Rock Hall - The beach, the marinas, restaurants, bars and shops. 15 minute drive to historic ...
From $300 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
- From $475 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 $475 per night (USD)VRBO
- From $155 per night (USD)
Expedia
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 $155 per night (USD)Expedia
- 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 $275 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 $275 per night (USD)Expedia
- 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
- 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 $337 per night (USD)
VRBO
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Stunning view overlooking the Chesapeake Bay, and a quick 5 minute stroll to scenic Betterton Beach! This historic wate ...
From $337 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 $278 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 $278 per night (USD)VRBO
- From $375 per night (USD)
Expedia
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 $375 per night (USD)Expedia
- From $320 per night (USD)
VRBO
Cottage on Chesapeake Bay with shared pool and dock. Near prime hunting areas.
- 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 $320 per night (USD)VRBO
- Click For Pricing
Expedia
Quaint cottage with amazing sunset views to soak up nature
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bay ...
Click For PricingExpedia
- From $425 per night (USD)
VRBO
Waterfront w\/private pier, pool, Hot Tub, kayaks and in town. Fireplace in LR.
- Bedrooms:
- 4
- 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 $425 per night (USD)VRBO
- From $1200 per night (USD)
Expedia
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Stunning waterfront property in Rock Hall. Expansive outdoor space with large pool and long pier on picturesque Swan Cre ...
From $1200 per night (USD)Expedia
- 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 $345 per night (USD)
Expedia
Eastern Shore beach cottage get-away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Recently renovated, charming cottage. A sandy beach is right across the quiet street from the cottage. The sandy botto ...
From $345 per night (USD)Expedia
- From $395 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 $395 per night (USD)VRBO
- From $275 per night (USD)
Expedia
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)Expedia
- From $800 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 $800 per night (USD)VRBO
- From $152 per night (USD)
Expedia
Country quiet 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 $152 per night (USD)Expedia
- From $172 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 $172 per night (USD)VRBO
- From $267 per night (USD)
Expedia
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)Expedia
- From $581 per night (USD)
VRBO
Lovely waterfront retreat on Fairlee Creek!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Goose Landing is a 3+ acre 4 bedroom 2.5 bathroom secluded waterfront home nestled on Fairlee Creek that boasts 350 feet ...
From $581 per night (USD)VRBO
- From $281 per night (USD)
Expedia
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 $281 per night (USD)Expedia
- 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 $175 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 $175 per night (USD)Expedia
- From $239 per night (USD)
VRBO
Ruby's Sea Glass Cottage near Betterton Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Have fun with the whole family at this cozy home in the center of Betterton, MD. You can walk to the beach to relax, fi ...
From $239 per night (USD)VRBO
- 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 $161 per night (USD)
VRBO
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 $161 per night (USD)VRBO
- From $255 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 $255 per night (USD)VRBO
- From $541 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 $541 per night (USD)VRBO
- 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 $596 per night (USD)
VRBO
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 $596 per night (USD)VRBO
- From $174 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 $174 per night (USD)VRBO
- From $240 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 $240 per night (USD)VRBO
- 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 $400 per night (USD)
VRBO
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 $400 per night (USD)VRBO
- From $322 per night (USD)
VRBO
3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
At 3 minutes walk to the beach, this Bayfront condo perched on a bluff in beautiful Betterton is a gem the whole year th ...
From $322 per night (USD)VRBO
- From $406 per night (USD)
VRBO
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 $406 per night (USD)VRBO
- From $206 per night (USD)
Expedia
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)Expedia