Easton, MD Vacation Rentals

Our Favorite Vacation Rentals in Easton

  • Historic Waterfront Property with Wi-Fi and Dock
     3br Home/Apartment
    HolidayLettings
    From
    $1,028
  • Large Historic Thomas Harrison House on Harbor in St. Michaels Town
    Good7br Home/Apartment
    HolidayLettings
    From
    $728
  • St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds
     6br Country House
    HolidayLettings
    From
    $1,666
  • Maryland’s Eastern Shore Welcomes You
     Home/Apartment
    HolidayLettings
    From
    $105
  • Lakeside Private Apartment
     Home/Apartment
    HolidayLettings
    From
    $173
  • Luxury Apartment with Private Entrance
     Home/Apartment
    HolidayLettings
    From
    $145
  • Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX
    ExcellentHome/Apartment
    HolidayLettings
    From
    $328
  • St. Michael's Premier in Town Summer Cottage!
    Excellent2br Home/Apartment
    Flipkey
    From
    $618

Check prices for these upcoming dates

Easton Vacation Rentals with a Pool

  • Miles River Guest House near Easton & St. Michaels
    Excellent4br Home/Apartment
    Airbnb
    From
    $367
  • Riverslie Estate on the Miles River
    Excellent5br Estate
    Airbnb
    From
    $1,101
  • TRUE SAINT MICHAELS 5.5 ACRE WATERFRONT w/POOL!!!!
    Excellent5br Home/Apartment
    Airbnb
    From
    $595
  • Miles Aweigh
    Excellent3br Cottage
    Airbnb
    From
    $333

Easton Vacation Rentals with Wi-Fi

  • Chesapeake Country Cottage: A Home Away From Home
    Excellent3br Home/Apartment
    Airbnb
    From
    $410
  • The Farm House at Hunting Creek
    Excellent5br Home/Apartment
    Airbnb
    From
    $480
  • LITTLE CREEK HIDEAWAY
    Okay3br Home/Apartment
    Airbnb
    From
    $396
  • Ole Miss Game Day Weekend Rental-Jackson Avenue
     2br Home/Apartment
    Airbnb
    From
    $678

Easton Pet-Friendly Vacation Rentals

  • EASTERN SHORE MARYLAND WELCOMES YOU
     Home/Apartment
    HolidayLettings
    From
    $102
  • Harrison House - in Town and on St Michaels Harbor
    Excellent6br Home/Apartment
    Airbnb
    From
    $808
  • ⋘ Lakeside Apartment ⋙| Private+Cozy Setting |
     Home/Apartment
    Airbnb
    From
    $227

Easton, Maryland Travel Guide

Located on the eastern shore of the Chesapeake Bay in Maryland’s Talbot County, Easton has consistently been ranked among the top 10 best small towns in America as well as the top 100 small arts communities in the country. Even though it has its roots back in the 18th century, Easton is known as a sophisticated town with excellent restaurants, outstanding lodging, an upscale historic district, and tons of attractions. Even though there are only roughly 17,000 permanent residents, there’s a thriving local community that makes all kinds of travelers feel at home. Eston is only an hour and a half from nearby Baltimore and Washington D.C., so it makes for a great little escape from the big cities. What’s more, getting out to explore the great outdoors is easier than ever. In the spaces surrounding Easton, you’ll find beaches, marshlands, and tons of protected ecosystems that make for excellent exploring.

Things to Do in Easton, Maryland

One of the best things to do in Easton is to learn about the region’s African American history. Visit the statue commemorating abolitionist Frederick Douglas, and tour the museums that stand to honor those who fought for equality.

For something lighter, check out the Avalon Theater, which is Easton’s go-to spot for live music and arts performances. The Avalon is an art deco gem, and each summer it hosts a jazz concert series that pulls talent from around the world.

Perhaps the event most associated with Easton is the annual Waterfowl Festival that takes place in November of each year. Easton’s event is known as the granddaddy of all waterfowl events as tons of people flock (pun intended) to the Chesapeake Bay for exhibits, workshops, music, and delicious cuisine.

Shopping may as well be considered a competitive sport here in Easton. There are tons of options from name-brand outlets to chic vintage finds that will keep any eager shopper occupied for more than a few days. Check out Bountiful Interiors, Dragonfly Boutique, Frugalicious, and Troika Gallery.

For the culture junkies, make sure to head over to the Academy Art Museum to see why Easton has been named one of the best small arts towns in America. And for the outdoors enthusiasts, hop on a scenic bike tour that explores the surrounding area.

Best Places to Stay in Easton, Maryland

If you’re looking to find the perfect vacation home around Eason, please use our search engine to find everything from unique houses to vacation homes, pet-friendly accommodations, vacation rentals with pools available in Easton, and everything in between. Use our search bar to access a list that offers a large selection of vacation rentals. Many of the options are close to the nearby state park, and most are great for family and friends. For those traveling with a four-legged friend, make sure to check the pet fees associated with your host.

Best Time to Visit Easton, Maryland

The best time to visit Easton depends on what you’re looking to do. Visiting during the summer means heat, lots of crowds, and increased prices. Visiting during the spring or fall means less of those things and more fun for you! Winters can get fairly cold here, especially taking the ocean breeze into account.

Price and Availability in Easton

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The cheapest day to stay at a vacation rental in Easton tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Easton tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Easton is in July, while the cheapest month is in February. The most popular time to book a vacation rental in Easton is in the high season in August. Easton has its low season in February, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Easton

Rainy days
73° 19°
7
66° 23°
4
66°
3
79° 18°
3
75° 27°
2
82° 33°
3
90° 45°
8
93° 52°
3
99° 56°
5
93° 61°
2
93° 57°
7
88° 36°
4
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Easton. The hottest month in Easton is June, when temperatures peak at 99 ˚F. The coolest month is December, when temperatures drop to 5 ˚F. The wettest month in Easton is August with 7.51 inches of rain, while the driest month is May with 1.68 inches of rain.

What Expert Travelers Think

  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
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  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

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  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide

Vacation Rentals in Easton

Pick the perfect vacation rental for your trip at AllTheRooms.com. We aggregate Airbnb, Priceline, Bed and Breakfast and more. AllTheRooms has 235 rentals, hotels and other great places to stay during your time in Easton, with everything from budget hostels and homestays to extravagant Airbnbs and hotels. A trip to Easton can be affordable - the cheapest price vacation rental is available at $34 per night. On average, a place to stay in Easton will cost you $355 per night.

Those needing to get some work finished during their trip to Easton can pick from 66 places to stay that include WiFi. We have 18 accommodations that come with breakfast included. Choose from 7 accommodations that provide gym facilities, so you don't miss a single workout. Driving to Easton? Then choose one of the 58 places to stay that comes with a parking spot included. We track 29 places to stay that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in one of 27 accommodations that are designated as pet-friendly.

We combine a wide variety of Easton accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 54 places to stay from Airbnb, 7 accommodations from Priceline and 3 places to stay from Bed and Breakfast.

112 of our accommodations in Easton have been reviewed and rated. 62% are rated excellent or good. You can instantly book any of 54 places to stay right now.

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