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Monday 9am - 5pm Tuesday 9am - 5pm Wednesday 9am - 5pm Thursday 9am - 5pm Friday 9am - 5pm Saturday 9am - 5pm Sunday 9am - 5pm

http://easternshorevacations.com/

Eastern Shore Vacations, 719 Goldsborough Street, Easton, MD (2024)

04/25/2023

FEATURED VACATION RENTAL | Creek Cottage at Reed Creek Farm
4 Beds, 4 Baths, 10 Guests
BOOK TODAY! https://bit.ly/3R5TYgm

Working Farm on Reeds Creek

This lovely working farm is on a peninsula situated between Grove Creek and (surely not to your surprise) Reed Creek, which is just off of the Chester River. On this peninsula, historically called Wright's Neck, sits the Reeds Creek house, built by Colonel Thomas Wright in 1775. The Creek Cottage, a second home on the property, is a modern addition to the 170-acre farm offering privacy in the presence of a historical setting.

Enjoy the private surroundings of the farm from the cottage's private pool or take a stroll or a leisurely bike ride to the sandy beach on Reed Creek. Get a sense of history by booking your stay at The Creek Cottage on Reed Creek Farm today.

04/25/2023

FEATURED VACATION RENTAL | The Water House
5 Beds, 6 Baths, 9 Guests
BOOK TODAY! https://bit.ly/35FdlJs

Over The River And Through The Woods!
Talbot County STR License STRN-22-18

Beautifully appointed with artwork and antiques, The Water House is a vacationer's dream! The natural surroundings, bright and airy rooms, and nautical location just outside of historic St. Michaels make this home the perfect getaway for discerning guests. Indoors and out, you'll have plenty of room to enjoy the best of Eastern Shore living. With direct access to Broad Creek and 1000' of waterfront, it's perfect for kayaking and paddle boarding!

04/25/2023

FEATURED VACATION RENTAL | Bayberry Cove
8 Beds, 5 Baths, 2HalfBaths 17 Guests
BOOK TODAY! https://bit.ly/3L5e5sr

Cozy Yet Spacious Waterfront Getaway!

This 8BR, 4BA, 2HBA warm, elegant, and inviting vacation rental awaits! This spacious waterfront property will make you feel right at home while you enjoy all of its splendid features, including a separate apartment above the garage. Situated at the end of a long, country lane in beautiful Dorchester County, you'll find a private retreat with room to roam, play, and swim.

With a full outdoor kitchen and pool, there's plenty to keep you busy and well entertained. Enjoy the gorgeous waterfront views and go fishing, paddleboarding or kayaking. Take advantage of all the natural beauty that surrounds you, then return indoors to all the comforts and conveniences of a wonderfully updated, well-appointed home.

04/03/2023

FEATURED VACATION RENTAL | Tranquil Waters
7 Beds, 6 Baths, 12 Guests
BOOK TODAY! https://bit.ly/39wJtB2

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

04/02/2023

FEATURED VACATION RENTAL | Seventh Haven
3 Beds, 2.5 Baths, 6 Guests
BOOK TODAY! https://bit.ly/3nsRGgF

An oasis of peace and relaxation!

This 3-bedroom, 2.5-bathroom shingle style cottage offers a character-filled interior and includes a good-sized living room. A waterfront oasis of peace and relaxation along Dixon Creek where you will experience beautiful sunsets while surrounded by mammoth oak trees on this 3.7 acre estate.

Further strengthening the attractiveness of this vacation rental are the Brazilian cherry floors and quartz countertops in the kitchen and breakfast area. Enjoy the wonderfully secluded backyard that comes complete with a screened porch and private dock.

The property has an ideal location. At the end of a tree lined street, you can enjoy tranquility and seclusion. Yet only 2 miles from Easton and 5 miles from St. Michaels, you have access to the best local shops, restaurants and activities in Talbot County. New to the market, it is truly a rare opportunity. Book this vacation rental before everybody else does!

Talbot County STR License ST-803-HOO

04/01/2023

FEATURED VACATION RENTAL | Riverslie
5 Beds, 4 Baths, 10 Guests
BOOK TODAY! https://bit.ly/3Kih7dR

Riverslie Estate on the Miles River!

Situated between Easton and Saint Michael's; Two charming historic Eastern Shore towns filled with fabulous shopping, dining, music, art, other attractions and family-friendly activities. The secluded, westerly facing location has outstanding views and sunsets. This historic 1840s“Farmhouse” Estate boasts high ceilings and original antique heart pine floors. A cozy modern family room, updated kitchen, and baths await guests.

Riverslie is a charming place to relax and get away. The screened porch and sweeping lawns lend for plenty of space to lounge or play. The historic charm of the home is not easily described. The original red hand blown stained glass oil lamp hangs, retrofitted with a lightbulb, in the foyer and bedrooms are tastefully decorated to suit the home.

Good for couples, solo and/or business travelers, families and big groups. Anyone who seeks a tasteful picturesque and otherwise interesting setting for a respite.

Besides the 13 acres immediately surrounding the house, guests can enjoy the adjacent 100 acre island, which is part of the property, and boasts a beautiful sandy beach directly across the water, as well as breeding families of bald eagles and other phenomenal wildlife and waterfowl.

Talbot County STR License STRN-22-42

04/01/2023

FEATURED VACATION RENTAL | Pride and Joy of Oxford
3 Beds, 2 Baths, 6 Guests
BOOK TODAY! https://bit.ly/3GrEbEP

In-town cottage with loads of charm and easy walking to parks and restaurants

Tucked away in the quaint, historic town of Oxford, Pride and Joy is a terrific spot for those looking to step back in time--when you could walk to the corner store for milk and ice cream, meander up the street to the local produce stand, or simply sit on the front porch and sip a lemonade while enjoying the scenery. The old fashioned charm and white picket fence are a warm welcome to visitors who want to slow it down a bit.

Pride and Joy's cheerful interior contributes to the allure and comfort you'll experience while delighting in its modern amenities. This is a perfect cottage for those wanting to enjoy nothing more than some peace and quiet and the respite that Oxford is known for.

03/31/2023

FEATURED VACATION RENTAL | Pine Forest Farm
7 Beds, 3 Baths, 12 Guests
BOOK TODAY! https://bit.ly/3nuXUN4

A Farm Fit for a Princess!
This 7-bedroom, 3-bathroom waterfront gem on the Chester River is tucked away, down a quiet dirt lane, hidden from the busy world around you. Situated on 60 acres, consisting of one main house and one detached cottage, your getaway awaits you from the moment you enter the grounds. You will be immediately surrounded by stunning Loblolly Pines, lush landscaping, peace and serenity. This is a nature lover's paradise, with a fascinating history.

Famous actress, Grace Kelly, Princess of Monaco, was known to visit the farm, along with her family, during the time that her father's business partner owned the farm and would host parties when she was a child. Locals in the area still recall her visits and have fond memories of the late Princes of Monaco.

At a super-convenient location in a peaceful Kent County neighborhood. Only a short car ride to the Calico Fields, Massey Air Museum, Crumpton Auction, street markets bars, grocery stores, local shops and restaurants. A rare and peaceful vacation opportunity.

We love this farm. You will too. Book today!

03/30/2023

JUST LISTED VACATION RENTAL | Quailsar Farm
5 Beds, 3.5 Baths, 10 Guests
BOOK TODAY! https://bit.ly/3Zu8C3L

Toto, There’s No Place Like This Vacation Home!

The impressive 5BR, 3.5BA vacation estate with a free-flowing floor plan features a beautifully maintained interior and large entertainment spaces. Enjoy the spacious kitchen that has been beautifully maintained and boasts stone-like countertops and a large center island.

The opulent main suite is the perfect place to unwind and dream. There's plenty of room to roam in the beautifully maintained backyard, which features dining space, salt water in-ground pool and rolling green lawn. Perfect for curling up with a good book. This is a pet friendly home, but pets must stay in the house and backyard only.

Enjoy a true sense of community in a sought-after section of Talbot County. Vacation in the rural lifestyle you've been waiting for! This unique rental won't last long. Book your stay today.

Talbot County STR License STN-22-36

03/30/2023

JUST LISTED VACATION RENTAL | Crew's Quarters
3 Beds, 2 Baths, 6 Guests
BOOK TODAY! https://bit.ly/3M4nByd

The Perfect Place to Relax!

Step into this idyllic, uniquely Eastern Shore Nanticoke mid- century home, perfect for friends and family, especially for multiple couples looking to be a short drive into the historic town of St. Michael's . This spacious 3-bedroom, 3.5-bathroom home was renovated top-to-bottom in 2022 with an open-design floor plan, formal dining room, and large entertainment spaces. Extra large windows through-out provide wonderful views open field farmland . The kitchen boasts commercial-grade appliances, granite countertops, and a center butcher block island to take entertaining to the next level.

The outdoor space is the perfect place to relax and entertain, with an open air pavilion complete with lounge seating, large dining table, propane grill, outdoor shower , a built-in heated swimming pool and hot tub, as well as a propane fire pit- perfect for late night star gazing . Bikes are conveniently stored in the garden shed.

Don't miss out on the opportunity to celebrate in this luxurious yet easygoing property.

Talbot County STR License STN-22-28

03/30/2023

JUST LISTED VACATION RENTAL | Commander's Getaway
3 Beds, 2 Baths, 6 Guests
BOOK TODAY! https://bit.ly/40EpTrY

A Cottage Created for Your Relaxation!

The impressive 3BR, 2BA Tilghman vacation home is designed with your comfort in mind, the free-flowing floor plan features a character-filled interior and comes complete with all first-floor bedrooms, relaxed living spaces and a flow-through living/dining area.

Overflowing with counter space and cupboards, this well-equipped beautifully maintained kitchen contains granite countertops and a breakfast bar.

The professionally landscaped outdoors offers a large deck outdoor and beautifully manicured lawn. A great spot for enjoying a morning cup of coffee or an evening cocktail. Perfectly positioned in a peaceful Tilghman neighborhood. Experience the best rural vacation living available in our area. Don't miss out on staying at this fabulous rental. Book your getaway today.

Talbot County STR License STN-22-34

03/11/2023

Save 5% when you book your next Eastern Shore getaway! Some exclusions apply.
https://bit.ly/41D9XaL

Enjoy 5% off the nightly rental rate of select properties. To qualify, book your next Eastern Shore getaway in March 2023 for a reservation occurring between May 27, 2023 & September 4, 2023.

Still have questions, special requests or would like a reservation specialist to book your vacation for you? Call 443-664-4039 or email [email protected].

Use promo code MARCH235 at checkout to receive the discount.

03/05/2023

FEATURED VACATION RENTAL | Oyster Haven
8 Beds, 5 Baths, 16 Guests
BOOK TODAY! https://bit.ly/3ERJqwr

This 3,800 square foot, 8-bedroom, 5-bathroom waterfront estate on Brooks Creek offers an unforgettable vacation experience. Imagine yourself watching beautiful sunsets with an abundance of wildlife while relaxing on the enormous front porch. Family gatherings have never been easier, with an oversized living room, huge dining room, spacious screened-in sunroom, a chef-inspired kitchen and detached guest house all situated on an expansive 16.5 acre yard.

If you’re looking for that shore lifestyle, this is the place for you! Enjoy an oversized private dock perfect for fishing, crabbing, launching kayaks and paddleboards, sitting around the firepit and making memories that will last a lifetime.

You will enjoy a prime location in a high-end section of Dorchester County. Just a 20-minute car ride to historic downtown Cambridge where you can experience local boutiques, restaurants, cafes, and bars.

A rare vacation rental opportunity. Book your stay today!

03/05/2023

FEATURED VACATION RENTAL | Neavitt Cottage
4 Beds, 2 Baths, 8 Guests
BOOK TODAY! https://bit.ly/3ERJqwr

Originally a waterman's cottage, Neavitt Cottage has been tastefully updated (super fast wifi!) while maintaining its original charm and character. Located along Balls Creek, which branches off the Choptank River, Neavitt Cottage's location in Neavitt provides a peaceful and quiet country setting, yet is just minutes away from all that St. Michael's has to offer. Enjoy crabbing, fishing, and sunset views off the dock, or relaxing on the large screened in back porch.

Neavitt Cottage offers an open floor plan featuring 2 first floor bedrooms and open kitchen, dining, and living areas. Two additional bedrooms and a full bathroom are upstairs.

Talbot County STR License ST-643-DER

03/04/2023

FEATURED VACATION RENTAL | Mill Creek
5 Beds, 3.5 Baths, 10 Guests
BOOK TODAY! https://bit.ly/3Jhwa7f

Located on the serene banks of Skipton & Mill Creeks, this home offers plenty of comforts disguised as contemporary cool. The open living area, situated on the second floor, includes a beautifully renovated kitchen, living room with fireplace, and spacious dining area. There are also two large en suite bedrooms and a deck that extends the living space into the outdoors.

The lower level boasts three additional bedrooms, a full bath, a large laundry room, and a family room with a bar that opens onto the pool-level patio. Enjoy the natural setting and water views from the deck, patio, and pool, or hop into one of the kayaks for a paddle around the creeks. The pier is a perfect place for bird watching or catching crabs.

Talbot County STR License ST-123-MIL

03/03/2023

FEATURED VACATION RENTAL | Miles Rest
4 Beds, 3.5 Baths, 8 Guests
BOOK TODAY! https://bit.ly/3IJLVSS

Built in 1930, this 4-bedroom, 3.5-bathroom waterfront getaway sits on 2.2 acres with 230 ft of shoreline along the Miles River offering expansive panoramic views. The ideal floor plan concept features a character-filled interior and provides an updated kitchen and first-floor bedroom with ensuite. Spread out upstairs in the comfortably sized main suite that benefits from an ensuite bathroom and walkout porch. Adding to the home's appeal are original and beautifully maintained hardwood floors throughout.

Relax at this enormous suburban getaway that features patio dining space, hot tub, built-in swimming pool, cabana house and beautifully manicured lawn. Lovely and serene. This is the perfect spot to detox from the hustle and bustle life throws your way.

Situated in a desirable area of Talbot County. Just a short 15 minute car ride to the quaint historic town of St. Michael’s and only 10 minutes from grocery stores, retail shops and restaurants in Easton. It’s rural living at its finest!

Be prepared to experience a vacation that you will never forget and never want to leave. Book your stay today!

Talbot County STR License ST-825-OAK

02/23/2023

FEATURED VACATION RENTAL | Lighthouse View
4 Beds, 3.5 Baths, 10 Guests
BOOK TODAY! https://bit.ly/3lNpNze

This 4-bedroom, 3.5-bathroom Chesapeake Bay waterfront, set upon 1 plus acres, is designed with your vacation in mind. The flexible floor plan features a sprawling interior and contains large flow through living areas, an expansive great room, soapstone kitchen countertops and wet bar for entertaining.

Sleep soundly in the opulent main suite that offers panoramic water views and separate sitting area. A true sanctuary, the primary bathroom provides heated floors.

The wonderfully secluded backyard features professional landscaping, 3 dining patios, a large in-ground pool, fire pit and views of Kent Island’s historic lighthouse. Enjoy the private dock, the perfect space for crabbing, fishing and watching the world go by.

A wonderful space for fun in the sun. Set on a quiet cul de sac in a desirable part of Queen Anne's County. Just 1 mile from the Cross Island Trail, 4 miles from the Blue Heron Golf Course & Driving Range, 6 Miles from the Mowbray Park tennis & pickle ball courts and 10 miles from some of the best restaurants, shopping, cafes, bars, wineries, nightlife, and mom-and-pop shops. All the perks of Queen Anne's County living are an easy drive away.

Take advantage of the best waterfront living around! See for yourself what this vacation rental has to offer. Book your stay before it’s gone.

02/22/2023

FEATURED VACATION RENTAL | Memory Lane
4 Beds, 2.5 Baths, 8 Guests
BOOK TODAY! https://bit.ly/3E5OWeu

We call this circa 1900 cottage gem "Memory Lane" for the wonderful memories you will create during your vacation. As self-proclaimed Scottish Creamery Fanatics', the cottage's close walk to Talbot County's best ice cream store wins first bragging rights. But walking to the ice cream store is only the beginning. You are one simple block to Oxford Beach called The Strand where you can bring your kayaks, paddleboards or simply a towel and a chair to lie on the beach, soak in the afternoon sun and search for sea glass.

Memory Lane's in-town location means never having to get in the car during your vacation - bike or walk to The Oxford Market, Wednesday's Farmers Market, Capsize waterfront restaurant, the expansive waterfront shaded park or Salter's Tavern at the Robert Morris Inn. This cottage's tranquil water-oriented decorating could be straight from an HGTV show - think updated design comfortably mingling with the Bay and its historic Oxford location. Additional touches such as a wet bar; board games and kids' toys make this vacation property home to all ages and are particularly child-friendly. Memory Lane is just like our favorite ice cream flavors - you can never get enough!

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