Chesapeake Bay Vacation Rentals in the Eastern Shore

We offer a wide variety of Eastern Shore vacation rentals in Maryland from St Michaels to Oxford and everywhere in between. Below you will find different Chesapeake Bay vacation rentals by category based on location or your desired amenities. You can choose vacation rentals that are great for large groups, rentals that have a pool and pet-friendly rentals. We truly have something for everyone as you book your Chesapeake Bay vacation! Start exploring today. We can't wait to help you find the perfect Maryland vacation rental.

Browse & Book Direct

It Pays to Book Direct! You have searched the travel websites. You have narrowed down your options and found your favorite rental property. You are ready to book. STOP RIGHT THERE! Booking through a travel website costs you more! Airbnb, VRBO, HomeAway, TripAdvisor, and others add significant fees when you book through them. Same for many online travel agencies. You can avoid these fees and save big by booking directly through ESVR. Theres no markup, and you can easily communicate any special needs or requests. Browse a Bigger Selection Heres another trick of the trade: If you browse through ESVR first, youll see every property we offer. Thats not always true with travel websites. Those sites dont list all vacation rentals because these listings are expensive for property owners. Along the North Carolina coast, for example, only 30% of all rental properties are listed on the major sites. That means you miss out. ESVR also has special offers, flash sales and off-season discounts that the major travel sites dont always list. Get the Inside Scoop Finally, the ESVR team can always give you the most updated information on our rentals and community. We tell you about new amenities, lesser-known area events, the best restaurants, and hidden gems. Book smarter, and book directly through ESVR. Youll save on your vacation and have a much better experience.

St. Michaels

St. Michaels Vacation Rentals These vacation rental homes are all convenient to historic St. Michaels, Maryland to enjoy dining, shopping, and sight-seeing. Please note prices given below are per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Less than weekly stays are typically a higher nightly rate and prices will vary based upon season and number of nights booked. For an exact quote, please input your dates on the property page.

Oxford

Oxford, Maryland Vacation Rentals Enjoy the quiet nautical ambiance of Oxford, Maryland by renting one of our village cottages or estate vacation rental homes on the outskirts of town. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Annapolis

Introducing our newest location and vacation rental selection in Annapolis, Maryland! Soak in all the charm that historic Annapolis has to offer for a weekend getaway or Naval Academy events. We are in the process of adding new Annapolis vacation home rentals in time for your Summer 2019 vacation, so please be sure to check back here often for the newest selection of vacation rentals.

Cambridge

With 1,700 miles of shoreline, Cambridge, Maryland is the perfect place to plan an Eastern Shore getaway. We offer a variety of vacation rentals in Cambridge including cottages and houses for rent. Many of our rentals are waterfront and feature a private pier where you can relax and take in the beautiful wide water views. Cambridge offers countless things to do including local dining and shopping, as well as exploring the Blackwater National Refuge. Browse our current vacation rentals in Cambridge, Maryland below. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Chestertown

Gorgeous Chestertown House Rentals on the Eastern Shore ESVR is now cultivating a portfolio of fine vacation house rentals in the Chestertown area! Perfect for our guests coming from the Philadelphia area or for those that just want to try a new place to vacation on the Eastern Shore. These rental properties offer privacy and the chance to explore the charming and quaint town of Chestertown, Maryland. We are constantly adding new house rentals to our Chestertown portfolio, so make sure to check back often for new properties. Book your Chestertown, MD rental today and browse our available properties below. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Pet-Friendly

Eastern Shore Pet Friendly Vacation Rentals Whats a vacation without your best friend? At Eastern Shore Vacation Rentals, we are happy to provide a variety of Chesapeake Bay pet friendly vacation rentals so that all members of the family can vacation together! Our rental properties are pet-friendly for dogs (two dog limit!) The Eastern Shore is the perfect place to vacation with your pet as there are many pet friendly beaches, restaurants, and outdoor activities. As always, there are no additional pet fees in our pet friendly rentals! Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Tilghman

Tilghman Island Rentals Looking for an "away from it all" vacation? Tilghman Island is a great option when you want an unspoiled and authentic Maryland vacation experience. Off the beaten path but close enough to St. Michaels to enjoy restaurants, shopping and sightseeing, Tilghman Island is the perfect place to escape. We feature a variety of Tilghman Island rentals including waterfront cottages and cozy vacation homes. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Homes with Pools

Maryland Vacation Rentals with Pools Make your Maryland Eastern Shore vacation one to remember and book one of our rental homes with a private pool! There is nothing like having your own refreshing private pool to cool off after a fun day on the water fishing, crabbing, or just sightseeing. Perfect for larger groups, many of these vacation rental homes come complete with lounging and patio furniture as well as grilling tools for the perfect backyard hangout! Our swimming pools are open from May 15-October 15. Some homes do offer pool heat at an additional charge; please inquire for more details. Also, note that the early and late parts of the season may affect water temperatures, however, pools are open to maintain the ambiance of the property. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Luxury Homes

Looking for more than just the comforts of home? Our luxury vacation home rentals offer extra amenities not found in your typical rental. Upscale furnishings and luxury touches such as a private swimming pool, dock, multiple acres, high-end kitchens or amazing outdoor spaces are found in many of our luxury rental homes on Marylands Eastern Shore. Feel free to browse these fantastic properties and make your vacation to the Eastern Shore one to remember! Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Multi Family Homes

If your idea of a vacation is reconnecting with loved ones or special friends, these properties provide just the ticket! Our larger homes sleep 10+ (please note in Talbot County 12 is the absolute maximum occupancy) and have amenities for all ages to enjoy. From refreshing swimming pools to private docks for fishing, kayaks, bikes and much more. Check out the selection of our multi-family vacation homes in the Chesapeake Bay area and please inquire about a specific homes amenities before booking. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Holiday & Events

There is always something happening on the Eastern Shore! Small town celebrations to big fireworks nights for the 4th, foodie and wine festivals and our signature Waterfowl Festival all provide something for everyone. Check your calendars and plan to join us!

View All Properties

Maryland Vacation Rentals: Cottages, Beach Houses, and Luxury Homes Check out the category groups below to find your next Eastern Shore vacation rental in Maryland! Located in and around the St Michaels area, our vacation rentals offer great opportunities for exploring, adventure and relaxing. Enjoy breathtaking scenic views of the ocean and bay, hot tubs, fire pits, and beautifully cared for properties. We offer a complete selection of vacation rentals including Maryland beach house rentals with breathtaking views, cozy cottages, and large family estate properties. Whether you are traveling as a couple, small family, or large group we have the perfect vacation rental for your Maryland getaway. Guests often take advantage of nearby fishing and crabbing holes as well as the area beaches and attractions. Whether you are looking to get outdoors, see the nearby towns, or spend the days on the sand, our wide variety of vacation rentals offer great amenities and features youll enjoy during your trip. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.