Kent Area Rentals
From $417 per night (USD)VRBO
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 $417 per night (USD)VRBO
From $1659 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 $1659 per night (USD)Expedia
From $407 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 $407 per night (USD)VRBO
From $379 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 $379 per night (USD)VRBO
From $258 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 $258 per night (USD)VRBO
From $500 per night (USD)Expedia
Wren Retweet- Country Estate in Center of C’Town
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
History with modern convenience, including first floor bedroom with private bath and super fast internet. Our house is ...
From $500 per night (USD)Expedia
From $1147 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 $1147 per night (USD)VRBO
From $159 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 $159 per night (USD)Expedia
From $315 per night (USD)VRBO
Brand New Cottage Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Professionally built vacation rental with charm and comfort! This 2 bedroom, 1 1/2 bath cottage is steps from the sandy ...
From $315 per night (USD)VRBO
From $642 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 $642 per night (USD)VRBO
From $1297 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 $1297 per night (USD)VRBO
From $1840 per night (USD)Expedia
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 28
Heated pool, hot tub, boat dock, and sauna! 5 acres of unobstructed Chesapeake Bay views and complete privacy. Surrounde ...
From $1840 per night (USD)Expedia
From $321 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 $321 per night (USD)VRBO
From $442 per night (USD)Expedia
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 $442 per night (USD)Expedia
From $565 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 $565 per night (USD)VRBO
From $565 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 $565 per night (USD)VRBO
From $685 per night (USD)VRBO
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 $685 per night (USD)VRBO
From $366 per night (USD)Expedia
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 $366 per night (USD)Expedia
From $407 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. There is a Holiday and special event suppleme ...
From $407 per night (USD)VRBO
From $302 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 $302 per night (USD)VRBO
From $757 per night (USD)VRBO
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Waterfront vacation home with breathtaking views. Sleeps 10, family suite + 3 bedrooms and two full baths. Open ro ...
From $757 per night (USD)VRBO
From $275 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 $275 per night (USD)Expedia
From $443 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 $443 per night (USD)VRBO
From $291 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 $291 per night (USD)Expedia
From $442 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 $442 per night (USD)VRBO
From $328 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 $328 per night (USD)Expedia
From $826 per night (USD)VRBO
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 $826 per night (USD)VRBO
From $725 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 $725 per night (USD)Expedia
From $1437 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 $1437 per night (USD)VRBO
From $326 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 $326 per night (USD)VRBO
From $293 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 $293 per night (USD)VRBO
From $598 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 $598 per night (USD)Expedia
From $433 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 $433 per night (USD)VRBO
From $409 per night (USD)Expedia
Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful 1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic ...
From $409 per night (USD)Expedia
From $454 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 $454 per night (USD)VRBO
From $882 per night (USD)VRBO
Breathtaking waterfront home on the Chester River
- Bedrooms:
- 4
- 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 $882 per night (USD)VRBO
From $481 per night (USD)VRBO
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 $481 per night (USD)VRBO
From $557 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 $557 per night (USD)Expedia
From $496 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 $496 per night (USD)VRBO
From $641 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 $641 per night (USD)Expedia
From $1631 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 $1631 per night (USD)VRBO
From $460 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 $460 per night (USD)Expedia
From $587 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 $587 per night (USD)VRBO
From $259 per night (USD)Expedia
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 $259 per night (USD)Expedia
From $432 per night (USD)VRBO
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 $432 per night (USD)VRBO
From $860 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 $860 per night (USD)VRBO
From $352 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 $352 per night (USD)VRBO
From $316 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 $316 per night (USD)Expedia
From $346 per night (USD)VRBO
Ruby's Sea Glass Cottage near Betterton Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
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 $346 per night (USD)VRBO
From $396 per night (USD)Expedia
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 $396 per night (USD)Expedia
From $220 per night (USD)VRBO
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 $220 per night (USD)VRBO
From $301 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 $301 per night (USD)VRBO
From $389 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 $389 per night (USD)VRBO
From $270 per night (USD)Expedia
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 $270 per night (USD)Expedia
From $340 per night (USD)VRBO
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 $340 per night (USD)VRBO
From $545 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 $545 per night (USD)Expedia
From $281 per night (USD)VRBO
Secluded Cottage in Middle of Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens ...
From $281 per night (USD)VRBO
From $5198 per night (USD)VRBO
Luxury Private Waterfront Compound on the Chesapeake Bay for 20+ Pool, Tennis...
- Bedrooms:
- 7
- Bathrooms:
- 13
- Sleeps:
- 30
Enjoy a private waterfront compound on the Chesapeake Bay designed for family reunions and large group gatherings. Set o ...
From $5198 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 $423 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 $423 per night (USD)Expedia
From $456 per night (USD)VRBO
Relaxing Cape Cod escape - pond overlook, in the heart of Rock Hall, sleeps 8.
- 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 $456 per night (USD)VRBO
From $316 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 $316 per night (USD)Expedia
From $284 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 $284 per night (USD)VRBO
From $422 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 $422 per night (USD)VRBO
From $866 per night (USD)VRBO
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 13
Rock Hall, fondly known as the “Pearl of the Chesapeake,” sits right on the shores of the Chesapeake Bay, where the pace ...
From $866 per night (USD)VRBO
From $424 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 $424 per night (USD)VRBO
From $666 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 $666 per night (USD)VRBO
From $701 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 $701 per night (USD)VRBO
From $556 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 $556 per night (USD)VRBO
From $360 per night (USD)Expedia
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 $360 per night (USD)Expedia
From $944 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 $944 per night (USD)VRBO
From $308 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 $308 per night (USD)Expedia
From $405 per night (USD)VRBO
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 $405 per night (USD)VRBO
From $282 per night (USD)Expedia
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 $282 per night (USD)Expedia
From $620 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. ...
From $620 per night (USD)VRBO
From $379 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 ...
From $379 per night (USD)Expedia
From $410 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 $410 per night (USD)VRBO
From $368 per night (USD)VRBO
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 $368 per night (USD)VRBO
From $1380 per night (USD)VRBO
A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 7
Welcome to Lovely Cove Farm. Close to Chestertown and Rock Hall for shopping and dining, but a world away. Secluded and ...
From $1380 per night (USD)VRBO
From $681 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 $681 per night (USD)Expedia
From $603 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 $603 per night (USD)VRBO
From $196 per night (USD)Expedia
Beachcomber Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your Downstairs Countryside Haven at The Still Pond Inn Step into serenity at The Beachcomber Suite, a thoughtfully des ...
From $196 per night (USD)Expedia
From $196 per night (USD)VRBO
High Tide Haven Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your 19th-Century Retreat in the Treetops at The Still Pond Inn Perched on the upper level of The Still Pond Inn, the H ...
From $196 per night (USD)VRBO
From $570 per night (USD)Expedia
The Waterfront Retreat- With Sauna and Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome To Paradise! Experience Waterfront luxury at this renovated retreat in a very quiet Chestertown neighborhood. T ...
From $570 per night (USD)Expedia
From $1297 per night (USD)VRBO
Eagles Point Landing-Private Pool, Dock, Pickleball
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
350 Acres, Private Pool, Dock, Pickleball and more Experience unparalleled privacy and endless natural beauty at Eagles ...
From $1297 per night (USD)VRBO
From $680 per night (USD)Expedia
Welcome to the magic of Langford Creek Farm
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A private riverfront estate on Maryland’s Eastern Shore, where rolling farmland, beautiful sunsets, and peaceful waterfr ...
From $680 per night (USD)Expedia
From $241 per night (USD)VRBO
Chesapeake Getaway - Marinas - Woodland Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to our peaceful retreat on Maryland's Eastern Shore, nestled in a quiet, wooded neighborhood near historic Cheste ...
From $241 per night (USD)VRBO
From $511 per night (USD)Expedia
Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This Rock Hall house boasts 3 inviting bedrooms, including a king, queen, and full bed. Guests enjoy 2 bathrooms with re ...
From $511 per night (USD)Expedia
From $623 per night (USD)VRBO
Private Waterfront Cottage On Langford Creek With Hot Tub & Pier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We invite you to come and enjoy this private waterfront cottage along the shores of Langford Creek. Located just a short ...
From $623 per night (USD)VRBO
From $338 per night (USD)VRBO
Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Experience Rock Hall like a local in this 3-bedroom ranch house. Large screened in porch to enjoy the outdoors. The bedr ...
From $338 per night (USD)VRBO
From $1855 per night (USD)VRBO
Holly Pointe Estate, Sleeps 25+ Pool, Pickle Ball
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 25
Welcome to Holly Pointe Estate, a private 90-acre luxury retreat overlooking the bay. Enjoy over 14,400 sq ft across the ...
From $1855 per night (USD)VRBO
From $336 per night (USD)Expedia
Walk to Historic Chestertown: Dog-Friendly Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fenced Backyard | Furnished Deck | Family Game Nights Step into a storybook at 'Sage Bungalow' in Chestertown, where hi ...
From $336 per night (USD)Expedia
From $174 per night (USD)VRBO
Turtle Cove Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked into the upper level of our peaceful farmhouse retreat, the Turtle Cove is a cozy, light-filled hideaway designed ...
From $174 per night (USD)VRBO
From $875 per night (USD)Expedia
Where luxury meets laughter by the bay. Welcome to Bamboo Sands Villa & Captain’s Quarters.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Where luxury meets COASTAL by the bay. A PERFECT SPOT FOR SPRING OR SUMMER GETAWAY! Enjoy the beach, soak in the views ...
From $875 per night (USD)Expedia
From $364 per night (USD)VRBO
Chesapeake Bay Getaway in Rock Hall
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to this newly built 3-bedroom, 2.5-bath home designed with a cozy coastal feel and modern touches throughout. Sip ...
From $364 per night (USD)VRBO
From $267 per night (USD)VRBO
Charming Room Rental for a Weekend Getaway on Maryland's Eastern Shore
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This charming room rental is located in a bed and breakfast on Maryland's Eastern Shore, and can accommodate up to three ...
From $267 per night (USD)VRBO
From $318 per night (USD)VRBO
3 Mi to Washington College! Updated Home w/ Patio
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Great Birdwatching | < 3 Mi to Marina | Day Trip to Rock Hall Morning light, crisp breezes, and a small-town vibe set t ...
From $318 per night (USD)VRBO
From $458 per night (USD)Expedia
Prime Rock Hall Location!! Restaurants, Boat Ramp, & Beach Within Minutes Away!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This charming house on Bayside Ave offers all the amenities one could ask for to include a roof top deck with hot tub. I ...
From $458 per night (USD)Expedia
From $466 per night (USD)VRBO
The BayBurst! Waterfront and Wonderful
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your cozy getaway awaits in Rock Hall at this waterfront peaceful house. With three bedrooms featuring one queen bed and ...
From $466 per night (USD)VRBO
From $228 per night (USD)VRBO
SWAN CREEK RETREAT This is a amazing garage apartment in Rock Hall
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Get ready to relax in this 1-bedroom apartment in Rock Hall. The perfect space features a comfortable king bed and a cle ...
From $228 per night (USD)VRBO