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Monday 10am - 5pm Tuesday 10am - 5pm Wednesday 10am - 5pm Thursday 10am - 5pm Friday 10am - 5pm Saturday 10am - 5pm Sunday 10am - 5pm

http://www.easternshorevacations.com/

Eastern Shore Vacation Rentals, 719 Goldsborough Street, Easton, MD (2026)

08/11/2026

Welcome to Sail Cove, a magnificent waterfront retreat nestled on Maryland's Eastern Shore near Easton, where the peaceful Chesapeake Bay region meets luxurious comfort and endless entertainment possibilities. This exceptional five-bedroom vacation home is your perfect escape for families and friends seeking an unforgettable getaway filled with water adventures, relaxation, and quality time together in a stunning natural setting.

A quintessential Eastern Shore farmhouse — freshly and extensively remodeled — perched high above one of the most unspoiled rivers on the eastern seaboard, with deep-water dockage and no development in sight.

Sleeps 10 · 5 Bedrooms · 3.5 Baths · Private Dock & Pool

Sail Cove sits adjacent to the storied Presquile mansion, reached by a spectacular sycamore-lined driveway that sets the tone the moment you arrive. The home perches high above the Wye River — widely regarded as one of the most beautiful waterways on the East Coast for its largely undeveloped, forested shorelines. Bald eagles, osprey, and great blue herons are regular companions on the water. Your view looks directly across to Wye Island — a 2,400-acre state wildlife preserve — where not a single structure breaks the tree line. Talbot County STR License STN-25-9

PROPERTY FEATURES:

Waterfront: Wye River
Dock: Private dock with a MLW 6' is available for guest use. Accommodates a 60 foot sail boat.
Pool: Private 18 x 32 saltwater pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.
Water Toys: 4 kayaks, 1 child kayak and 1 paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.
Land Toys: Corn hole and badminton are available for guest use.
Hot Tub: Hot tub is available for guest use.
Grill: Propane grill. Propane is provided.
WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

05/07/2026

https://easternshorevacations.com/vacation-rentals/m/properties/bayview-20/

JUST LISTED Escape to Bayview 2.0, a stunning waterfront retreat within a few miles of charming St. Michaels. Designed for unforgettable getaways, this expansive estate comfortably hosts up to 12 guests on a property that spans more than twelve acres. This home was crafted to deliver comfort, privacy, and relaxation.

Wake up to sweeping views of the Chesapeake Bay and end your evenings with breathtaking, golden sunsets right outside your door. This expansive waterfront property boasts six beautifully appointed bedrooms each designed to provide a serene and comfortable escape. Four of the bedrooms have an ensuite full bathroom. Four bedrooms have king size beds, another bedroom has two king size beds and the sixth bedroom has a queen bed. All are equipped with premium linens and modern amenities. The first floor master bath provides a spa like experience. There are also two ½ baths and an outdoor shower. This home has majestic views of Chesapeake Bay and the sunsets are picturesque and unforgettable. Step into the open concept living and dining areas, where you will find an elegantly designed kitchen complete with top of the line appliances, extensive counter space and a cozy waterfront breakfast nook. The screened in porch offers comfortable seating with views of the Chesapeake Bay and the beautiful patio and pool. The living room is perfect for unwinding after a day of swimming and exploration with plush sofas, a smart TV and fireplace available for guest use.

Outside you will find a beautifully landscaped waterfront with a dock, ideal for fishing or simply soaking in the tranquil surroundings. This property also features a heated pool, hot tub and BBQ area perfect for gatherings and outdoor entertaining.

The historic town of St. Michaels is a short 10 minute drive away and offers an array of shopping with fine and casual dining. Spend a day exploring the Chesapeake Maritime Museum, the St. Michaels nature trail and the historic downtown walking tour. You are within driving distance of the historic Harriet Tubman Underground Railroad Scenic Byway and the Blackwater National Wildlife Refuge. The town of Easton, a 22 minute drive from the home, has extensive shopping, dining and attractions that include the Academy Art Museum, Prager Auditorium and the Pickering Creek Audubon Center. The Avalon Theater provides dynamic arts, education and cultural programming. There are public and private golf courses in the area as well as public tennis courts.

Whether you are seeking a relaxing family vacation or a fun filled getaway with friends, Bayview 2.0 promises an unforgettable stay. Book now and make this luxurious waterfront haven your home away from home. Talbot County STR License STRN-26-11

https://easternshorevacations.com/vacation-rentals/m/properties/bayview-20/

01/21/2026

JUST LISTED
Sunset Shores
Royal Oak, MD
4 Beds
2.5 Baths
8 Guests

https://easternshorevacations.com/vacation-rentals/m/properties/sunset-shores/

Welcome to Sunset Shores, your perfect waterfront retreat in St. Michaels, Maryland! This stunning 4-bedroom, 2.5-bathroom home offers a luxurious escape for up to 8 guests. As you step inside, you'll be greeted by an open-concept living area with a fully equipped kitchen, perfect for preparing delicious meals. The living room is cozy and inviting, with a fireplace to keep you warm on cooler evenings.

The master bedroom features a plush king-sized bed, while the second bedroom also boasts a king-sized bed for ultimate comfort. The third bedroom has two full-sized beds, and the fourth bedroom offers a bunk bed, full over queen, for the kids. All bedrooms are tastefully decorated and provide a serene space to unwind after a day of exploration.

Sunset Shores offers a range of premium amenities, including free Wi-Fi, a private pool, and waterfront access with a dock. You'll also find a dishwasher, dryer, and all necessary kitchen essentials for your convenience.

Book your stay at Sunset Shores today and experience the ultimate in waterfront luxury. We can't wait to welcome you to our beautiful home! Talbot County STR License STN-25-18

PROPERTY FEATURES:

Waterfront: Bridge Creek
Dock: Water and electricity available for guest use. Guest can tie boat to dock but boat lift is NOT available for guest use.
Water Toys: 2 kayaks are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.
Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.
Grill: Built-in propane grill. Propane is provided.
WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

BED SIZES:

King - 1 / King - 1 / Double Bed - 2 / Bunk Bed - Full over Queen - 1 /

https://easternshorevacations.com/vacation-rentals/m/properties/sunset-shores/

01/12/2026

Miles End
Easton, MD
5 Beds
6 Baths
10 Guests

https://easternshorevacations.com/vacation-rentals/m/properties/miles-end/

Welcome to Miles End, a breathtaking waterfront estate that seamlessly combines luxury and nature on 26 sprawling acres. Perfectly suited for nature enthusiasts, cyclists, sportsmen, and large families, this enchanting vacation rental boasts 800 feet of pristine water frontage and picturesque farmland.

As you step inside, you'll be greeted by a stunning first floor featuring a fabulous screened porch, a sunlit great room, and an elegant formal dining room, all flowing into a gourmet kitchen and cozy family room with a wet bar. The luxurious primary suite is a true retreat, complete with a private deck, fireplace, whirlpool bath, and sauna.

Venture to the second floor, where you'll find four spacious bedrooms, each with en suite bathrooms and private waterside balconies, along with a colossal recreation room perfect for entertaining, featuring a bar, fireplace, billiards, and foosball. The third floor offers a bonus room with its own private balcony, sitting area, and full bath, ensuring plenty of space for relaxation or family gatherings.

Step outside to discover meticulously landscaped grounds complete with a refreshing pool, serene koi pond, crackling fire pit, and private dock. With ample space for outdoor activities like badminton and croquet, and paddle boards and kayaks available for river exploration, you’ll be immersed in your own nature sanctuary, where you can observe heron, osprey, bald eagles, and other wildlife. Talbot County STR License ST-24-31

PROPERTY FEATURES:

Waterfront: Miles River
Dock: Private dock, including attached floating dock. Boat lift is not for guest use, but boats may be tied to dock. Water is tidal and can become shallow.
Water Toys: 2 kayaks and 1 paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.
Pool: Private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.
Grill: Propane grill. Propane is provided.
WiFi: High-speed internet (fiber broadband to house)

11/25/2025

Eastern Shore Vacation Rentals

Save This Year | Stay Next Year
10% off the nightly rate

https://easternshorevacations.com/vacation-rentals/m/custom-groups/promotions/

Promo Code:
10OFF2025

Details:
Must book a reservation of 7-nights or more.
Book between 11.24.2025 - 12.31.2025
Stay between 5.21.2026 - 9.13.2026
Offer cannot be applied to reservations made prior to this promotion.
Offer cannot be combined with any other promotions.
Discount of 10% will be applied only to the nightly rate of the stay.
All getaways will be subject to our standard cancellation policy.

https://easternshorevacations.com/vacation-rentals/m/custom-groups/promotions/

10/01/2025

Tranquil Waters
Tilghman, MD
7 Beds
6 Baths
12 Guests

https://easternshorevacations.com/vacation-rentals/m/properties/tranquil-waters/

Looking to getaway, relax and recharge?

This newly renovated coastal 7-bedroom, 6-bathroom waterfront getaway with a spa-like indoor pool (heated during the winter months ) featuring a cabana house, 4,000+ square foot of living space, and breathtaking panoramic views of Harris Creek flowing into the Chesapeake Bay.

Tranquil Waters offers 3 living room spaces, 2 fireplaces, an updated kitchen, a formal open dining room and a half bathroom on the main floor. The indoor pool house faces the water and features a game room and full bathroom for year round use. Just a short drive to historic St Michaels with boutique restaurants and shops.

Tranquility at its finest! Walk out onto your private dock to fish, kayak, boat, have dinner, bird watch and more! This is the perfect vacation home for those looking to getaway, relax and recharge. Talbot County STR License STRN-23-10

PROPERTY FEATURES:

Waterfront: Harris Creek
Dock: Private dock.
Pool: Indoor pool. Swimming pool is open all year for guest use. Be sure to bring your own pool towels. Heat is available for an additional fee. Please contact us if you want to add this option.
Pool House: Bathroom, shower and game room available for guest use.
Grill: Pellet grill.
WiFi: Complimentary Wi-Fi for guest use.

BED SIZES:

King - 1 / King - 1 / Double Bed - 1 / Bunk Bed - Pyramid | Single over Double - 1 / King - 1 / Single Bed - Twin Sized - 1 / Bunk Bed - Pyramid | Single over Double - 1 / Queen - 1 /

https://easternshorevacations.com/vacation-rentals/m/properties/tranquil-waters/

09/18/2025

The Eagle’s Nest
Grasonville, MD
5 Beds
4 Baths
14 Guests

https://easternshorevacations.com/vacation-rentals/m/properties/the-eagles-nest/

Soar above the everyday. Vacation like a legend.

This waterfront oasis in Queen Anne's County offers an escape that blends classic comfort with rockstar-level relaxation. Picture yourself gliding down the tree-lined drive to a sprawling 5-bedroom, 4-bathroom colonial, where a chef-inspired kitchen and spacious entertaining areas await.

Retreat to the oversized main suite, complete with a remodeled ensuite boasting heated floors, a soaking tub, and a two-person shower. Outside, a meticulously maintained backyard beckons with an outdoor dining patio, a crackling fire pit, and a private dock overlooking spectacular views.

This is more than a rental; it's a destination where unforgettable memories are made. Book your stay today.

PROPERTY FEATURES:

Waterfront: Little Greenwood Creek
Dock: 40’ “L” shaped private pier with 3ft MLW. Electricity and water available for guest use.
Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Heat is available for an additional fee. Please contact us if you want to add this option.
Grill: Propane grill. Propane is provided.
WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

BED SIZES:

King-1 / King - 1 / Single Bed - Twin Sized - 2 / Queen - 2 / Queen - 1 / Queen - 1 /

https://easternshorevacations.com/vacation-rentals/m/properties/the-eagles-nest/

09/09/2025

Lighthouse Haven
Stevensville, MD
6 Beds
4.5 Baths
14 Guests

https://easternshorevacations.com/vacation-rentals/m/properties/lighthouse-haven/

Experience the ultimate getaway at this gorgeous Kent Island waterfront! This 4,600 square-foot, 6-bedroom, 4.5-bathroom Long Creek waterfront retreat on over 2.6 acres of private land is perfect for your family vacation. The main level features a beautifully renovated kitchen, a dining room seating up to 12, and a breakfast area with stunning water views and sunrise vistas.

This property features two entertainment indoor areas for all ages. The lower level of the main house serves as a lively entertainment hub, complete with a full bar and a billiards table, perfect for evening relaxation or friendly competition. When you step out to the backyard, you’ll find the huge detached game lounge, housing a variety of games including table tennis, air hockey, foosball, co****le, darts, and arcade basketball hoops. An 86-inch screen TV with lounge seating provides the perfect spot for watching your favorite sports.

PROPERTY FEATURES:

Waterfront: Long Creek
Dock: 140ft x 6ft private dock with MLW 4 ft. Electric and water, including a sink available for guest use. 2 crab traps are provided. Guests are not permitted to tie a boat to the dock.
Water Toys: 1 two-person kayak, 1 tandem kayak, and 1 stand up paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.
Pool: 16 x 32 private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.
Fireplaces: Outdoor gas fireplace table on the deck is available for guest use.
Firepit: Outdoor firepit available for guest use.
Grill: Propane grill. Propane is provided.
Land Toys: Pickleball court (with paddles & balls), outdoor Basketball hoops, billiard, table tennis, foosball, Dart Board, co****le, Arcade basketball hoop, available for guest use. 2 adult bikes.
WiFi: 1000 mpbs, reliably fast (good for 8-10 people or up to 12 devices)

09/08/2025

Blue Bay Haven
Stevensville, MD
7 Beds
5.5 Baths
16 Guests

https://easternshorevacations.com/vacation-rentals/m/properties/blue-bay-haven/

Experience spectacular sweeping views of the Chesapeake Bay Bridge from this fully renovated, well-appointed 7-bedroom, 5.5-bath waterfront home, just minutes from downtown Annapolis!

The main level is designed for entertaining, featuring a great room with an open kitchen concept, an oversized island with seating for six, and a cozy seating area. Enjoy meals with family and friends in the light-filled sunroom that comfortably accommodates twelve.

Discover the secret Pirate’s Cave hiding next to the laundry room, a fun-filled game room with a big screen TV equipped with table tennis, darts, air hockey, and foosball—perfect for all-day entertainment with family and friends. The brand new 20x40 swimming pool offers a basketball hoop and a relaxing tanning ledge where you can watch the sun set behind the Bay Bridge. The pool area is adjacent to a covered gazebo deck, an ideal spot for enjoying a crab feast from one of the local restaurants or a glass of wine.

Gather around with drinks on the rear deck outfitted with a gas fire pit and plenty of seating. Or sit around the fire pit in the backyard making smores and watching the night sky. Younger guests will be thrilled by the pirate-inspired treehouse and play area, featuring a climbing wall, pirate plank, swings, slide, hammock, and treehouse!

PROPERTY FEATURES:

Waterfront: Chesapeake Bay.
Pool: 20 x 40 private pool with a basketball hoop. Swimming pools are open from May 22 - October 15. Be sure to bring your own pool towels.
Dock: 150 ft x 6 ft private dock for fishing and crabbing.
Game Room: Billiards, ping pong table, air hockey, foosball, and darts
Outdoor activities: co****le, basketball hoops and Tree house.
Grill: Propane grill. Propane is provided.
Fireplaces: Outdoor gas fireplace table.
Pet Policy: Pets are not permitted.
WiFi: 1000 mpbs, reliably fast (good for 8-10 people or up to 12 devices)

08/28/2025

Eastern Shore Vacation Rentals
PROMOTIONS
https://easternshorevacations.com/vacation-rentals/m/custom-groups/promotions/

3 Nights for the price of 2 *
To qualify for this LIMITED TIME offer:
Must book a 3-night stay or more at Wade A Minute Chester or The Weekender
Must use promo code: FALL3FOR2

4 Nights for the price of 3 *
To qualify for this LIMITED TIME offer:
Must book a 4-night stay or more at Chesapeake Pines, Clearview, Ferry View, Mill Point, Neavitt Cottage, The Bird’s Nest, Wade A Minute Chester, The Weekender or Windward Cove
Must use promo code: FALL4FOR3

5 Nights for the price of 4 *
To qualify for this LIMITED TIME offer:
Must book a 5-night stay or more at Clearview, Down By The Docks, Mill Point, Neavitt Cottage, The Eagle's Nest or Wade A Minute Chester
Must use promo code: FALL5FOR4

* To qualify for this LIMITED TIME offer:
Must book between 8.5.2025 - 10.15.2025
Must stay between 9.1.2025 - 1.5.2026
Lowest night FREE
Offer cannot be applied to reservations made prior to this promotion.
Offer cannot be combined with any other promotions.
Discount will be applied only to the lowest nightly rate of the stay.
All getaways will be subject to our standard cancellation policy.

Eastern Shore Vacation Rentals

08/11/2026

05/07/2026

01/21/2026

01/12/2026

11/25/2025

10/01/2025

09/18/2025

09/09/2025

09/08/2025

08/28/2025

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Monday	10am - 5pm
Tuesday	10am - 5pm
Wednesday	10am - 5pm
Thursday	10am - 5pm
Friday	10am - 5pm
Saturday	10am - 5pm
Sunday	10am - 5pm