Luxury chesapeake bay vacation rentals

Luxury chesapeake bay vacation rentals DEFAULT

Eastern Shore Vacation Rentals

Eastern Shore MD Areal shot

Specializing in unique vacation properties in the charming towns of the Eastern Shore of the Chesapeake Bay. Offering a boutique selection of cottages, waterfront homes and estates.

chairs by the water in Eastern Shore MD

Our hand-selected portfolio of Eastern Shore, MD, vacation rentals includes properties ranging from quaint historic cottages, waterfront vacation homes or estate luxury properties offering the very best of Eastern Shore living. Our pet-friendly rentals cater to the whole family so there’s no need to leave your furry friends behind! Our warm, friendly and knowledgeable staff adds an extra special personalized touch to your dream vacation and our effortless search and booking process ensures an unrivaled Chesapeake Bay vacation experience with the privacy, space, comfort, and amenities of home…simply a click away!

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Discover the beauty and fascinating maritime heritage of Maryland’s Eastern Shore as you explore miles of pristine shoreline dotted with charming towns, historic sites, scenic wildlife refuges and breathtaking sunsets across the Chesapeake Bay. Head to the harbor in St. Michaels, the “Heart & Soul of Chesapeake Bay”, for a ride on the historic skipjack or cross the drawbridge to the traditional quaint waterman’s village of Tilghman Island. Immerse yourself in nature at the Blackwater National Refuge in Cambridge, roam the streets of Easton voted the “8th Best Small Town in America”, watch the sailboats passing by in Oxford, one of the oldest towns in America or stroll along the brick sidewalks in the historic college town of Chestertown. Wherever you choose to lay your hat, we have the perfect Eastern Shore vacation home for you to complete your visit.

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All-Inclusive Pricing – our prices include everything you need for a relaxing vacation: bed and bath linens, beds made upon arrival, and all other fees (except state and local tax!).

  • No Pet Fees – No need to leave your best friend behind! Many ESVR homes are dog-friendly and dogs travel free (two dog limit, please).
  • Best Price Guarantee – For the best pricing, promotions and last minute deals, check our website frequently and book directly with us. No unnecessary service fees!

Read Our FAQs

Management Services - two chairs on a porch in day

Eastern Shore Vacation Rentals specializes in marketing and managing short-term vacation rentals – it’s all we do! Vacation rentals are currently the fastest growing segment of the tourism industry and we understand the booking trends! We value both our guests and homeowners and our goal is to maximize your Eastern Shore rental income while offering proactive property care and management to the owner and upscale amenities and top-notch service to our guests. Our state-of-the-art website, unparalleled marketing, and online booking process optimize the booking of your property and our expertise in the vacation rental industry ensures your vacation home is in the best hands. Please contact us, one of our friendly team members is standing by to discuss our Maryland based property management services and how we can best partner with you to grow your investment.

Learn More

  • Locally owned and operated
  • Office close to your rental

Choose the perfect vacation rental

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Best Vacation Home Deals in Chesapeake Bay

Recommended Vacation Rentals in Chesapeake Bay

Find your perfect vacation rental in Chesapeake Bay: from $70 per night

Vacation rentals with Wi-Fi

Vacation rentals and apartments with air conditioning

Apartments and vacation rentals with a kitchen

Popular Rental Amenities in Chesapeake Bay

Using our filters will help you find the perfect vacation rental in Chesapeake Bay. HomeToGo's data highlights that "internet" and "TVs" turn out to be the most frequently offered features in Chesapeake Bay. Plan your vacation in advance if you want to sweat it out in a sauna or you want a rental with a jacuzzi. There are just 207 listed accommodations providing "saunas" and 634 properties including "Jacuzzis."

The Weather in Chesapeake Bay

The above is a climate diagram for Chesapeake Bay. During July, maximum temperatures go up to more than 87° However, temperatures can go lower than 28° in Chesapeake Bay in January. The rainiest month is January while the driest month is November.

7-Day Weather Forecast in Chesapeake Bay

Sat, 23 Oct

Sun, 24 Oct

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Summerlee - Luxury Chesapeake Bay Waterfront with Sandy Beach!

4.9/5 Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 12

Popular amenities

  • Kitchen
  • Air conditioning
  • Pet friendly
  • Washer
  • Dryer
  • Outdoor Space

Explore the area

  • Confederate Memorial Park3 min drive
  • Point Lookout State Park3 min drive
  • Kitts Point21 min drive
  • Leonardtown, MD (LTW-St. Marys County)36 min drive

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Summerlee - Luxury Chesapeake Bay Waterfront with Sandy Beach!

Beachfront Scotland vacation home in Point Lookout with kitchen

Summerlee awaits you (5 bedrooms, 5 baths total). This classic beach house has been fully renovated and luxuriously appointed. The house features an open floor plan for easy entertaining. Situated directly on Chesapeake, hear the waves while you cook, read or relax; see diverse wildlife including, herons, swans, ospreys, bald eagles, and pelicans through expansive glass doors, from the screened-in porch, the wrap-around deck or the large deck off the master bedroom. Or, grab a beach chair or towel and head for the private sandy beach. The open floor plan, complete with a large kitchen, dining room, 2 sitting rooms and a TV room allows a large family or group to be together whether cooking, playing games, watching television or just relaxing. A crackling fire in the wood burning fireplace makes winter days at Summerlee as enticing as summer days. Enjoy a weekend wine tasting at nearby Woodlawn plantation.

A short-bike ride away is Point Lookout State Park, a Civil War site. Today the park, which is located at the intersection of the Chesapeake Bay and the Potomac River, hosts miles of protected land set aside for biking, kayaking**, boating, fishing, camping or enjoying nature as well as a museum that provides a historical perspective on the region. Or charter a boat at one of many local marinas for a day of fishing on the Bay. Another nearby historical site is St. Mary's City (10 miles), the original capital of Maryland. Visitors are 25 minutes from dining and shopping on Solomon's Island or in historic Leonardtown. Or enjoy one of several local marina restaurants. Want a day trip away? All that the nation's capital has to offer is a short 80 miles away.

Collect shells and beach glass while walking uninterrupted for miles along the sandy beach. Unlike typical cheek-by-jowl beach houses, Summerlee offer its visitors bayfront accommodations on an acre of land. Enjoy rare waterfront privacy so close to major cities and amenities.

**Kayaks will not be available during late fall, winter, and early spring periods due to concerns regarding guest safety due to low water and air temperatures.

Keywords: private beach house; open floor plan,;glass-enclosed;Chesapeake beach-front

Air-conditioned accommodations at this vacation home offer fireplaces and coffee/tea makers. Rooms open to balconies. Kitchens offer refrigerators, stovetops, microwaves, and cookware/dishes/utensils. Additionally, rooms include hair dryers and irons/ironing boards.

The recreational activities listed below are available either on site or nearby; fees may apply.

Property manager

Peggy Binzel

Speaks English

Property amenities

Parking and transportation


  • Refrigerator

  • Stovetop

  • Microwave

  • Oven

  • Dishwasher

  • Ice maker

  • Cookware/dishes/utensils

  • Toaster

  • Coffee/tea maker


  • 5 bedrooms

  • Bed sheets provided


  • 5 bathrooms

  • Hair dryer

  • Towels provided


  • TV with cable/satellite service

  • Video library


  • Washing machine and dryer


Services and conveniences

Things to do

  • Kayak on site

  • Bicycling on site

  • Swimming nearby

  • Hunting nearby

  • Cycling nearby

  • Kayaking nearby

  • Sailing nearby

  • Birdwatching nearby

  • Hiking nearby

  • Hiking/biking trails nearby

  • Winery tours nearby

Safety features

  • Carbon monoxide detector

  • Smoke detector

  • Deadbolt lock


  • Sleeps 12

  • Unit size: 3200 sq ft (297 sq m)


Check-in time starts at 4:00 PM

Minimum check-in age - 25


Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions


Pets allowed

Restrictions apply; for more information contact the property at the number on the booking confirmation

Children and extra beds

You need to know

This property is managed by a private host, not a professional engaged in trade or business

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

Onsite parties or group events are strictly prohibited

Safety features at this property include a carbon monoxide detector, a smoke detector, and a deadbolt lock

This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

Guests can arrange to bring pets by contacting the property directly, using the contact information on the booking confirmation

A car is required for transportation to and from this property

Property is also known as

Summerlee Luxury Chesapeake Bay Waterfront Sandy Beach House

Summerlee Luxury Chesapeake Bay Waterfront Sandy Beach Scotland

Summerlee Luxury Chesapeake Bay Waterfront Sandy Beach

Summerlee Luxury Chesapeake Bay Waterfront Sandy Beach Scotland

Summerlee Luxury Chesapeake Bay Waterfront Sandy Beach Scotland

Summerlee Luxury Chesapeake Bay Waterfront Sandy Beach

Summerlee Luxury Chesapeake Bay Waterfront With Sandy Beach!

Summerlee Luxury Chesapeake Bay Waterfront Sandy Beach House

Summerlee Luxury Chesapeake Bay Waterfront Sandy Beach

Summerlee Luxury Chesapeake Bay Waterfront With Sandy Beach!

What's nearby

  • Confederate Memorial Park - 3 min drive
  • Point Lookout State Park - 3 min drive
  • St. Mary's College of Maryland - 19 min drive
  • Kitts Point - 21 min drive
  • Elms Beach Park - 21 min drive


  • Courtney's Restaurant & Seafood — 12 min drive
  • Sunset Cove Waterfront Restaurant — 13 min drive

Overall score and ratings

Rating 5 - Excellent. 53 out of 58 reviews

5 - Excellent


Rating 4 - Good. 4 out of 58 reviews

4 - Good


Rating 3 - Okay. 1 out of 58 reviews

3 - Okay


Rating 2 - Poor. 0 out of 58 reviews

2 - Poor


Rating 1 - Terrible. 0 out of 58 reviews

1 - Terrible


Write a review

5/5 Excellent

Alice M.

Oct 6, 2021


My family gathered for two nights at the Summerlee house to celebrate our mother's 90th birthday and the setting exceeded our expectations! We spent much of our time together on the screened in porch marveling at the view of the ever-changing water and sky (it almost felt as if you were floating on the water!), enjoying the Bay breezes and soft air, and watching the butterflies, gulls, herons, cormorants and eagles fly by. We kayaked, swam, took the bikes for an outing, and cooked together in the large and well-stocked kitchen. The bedrooms - each with their own bathrooms were comfortable and private, and the open living/dining/kitchen plan was wonderful. AND - we loved the outdoor shower! Gathering with each other in such a beautiful setting was a delight - we hope to be back soon.

4/5 Good

Melissa S.

Aug 28, 2021

Beautiful views at this relaxing location

Lots of spots to sit & read or take in the views. The wrap-around deck was wonderful. It’s a wooded location so be prepared to sweep off a spot (brooms provided) & wipe down some seats (bring a few rags & some cleaning supplies for the outside furniture). The inside was nice & clean & well-appointed. It was pouring rain when we arrived so I was happy to find some old towels in the car that we used as door mats inside so we wouldn’t track mud inside. We spent our week relaxing on the beach, reading in the screened in porch or on the deck, kayaking & crabbing. It was nice to be forced to slow down & take it all in without running from one attraction to the next!

5/5 Excellent

Suzanne M., United States

Aug 23, 2021

Family time at the Bay

We have been coming to the Scotland Md properties for years, but this was the first time with our granddaughter as a toddler. Summerlee was perfect for us. The lower level was quiet for toddler naps and bedtime while the adults enjoyed the main level. We were able to section off a sitting room as a play area. The beach is steps away. The views are amazing and we love the porch. It was the perfect family get away. Another note: our greyhound needed medical attention and Breton Vet took our dog on short notice and gave wonderful care.

5/5 Excellent

Kathleen C.

May 25, 2021

Lovely stay

The cottage and the location are more beautiful than the photos. Thank you for a lovely vacation

5/5 Excellent

Deborah W.

May 6, 2021

Made Many Memories at Summerlee

Views, space, charm, this house had it all! We just loved our time at this beach front rental. The interior was decorated with comfortable elegance and the outdoors was surrounded by nature’s best, including a nesting osprey couple!

INSIDER SECRETS: Finding The Perfect Luxury Vacation Rental

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An Inspiring Waterfront Estate on Maryland’s Eastern Shore - TTR Sotheby's International Realty

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