Easton holiday rentals

We found 596 holiday rentals — enter your dates for availability
Discover a selection of 32 homes and other holiday rentals in Easton that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for spending time at your holiday home, which might include a garden and pool. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Easton

Showing deals for:13 Nov - 20 Nov

Exterior
Kitchen
Kitchen
Kitchen
Exceptional
(28 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

12% off
AU$3,002
for 7 nights, 1 room
AU$429 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
screened porch
Pool
View from Foyer into Great Room
Dining table- seats 10!
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
AU$11,091
for 7 nights, 1 home
AU$1,584 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Interior
Private kitchen
Room
Outdoor dining
Exceptional
(20 reviews)

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis

16% off
AU$8,184
for 7 nights, 1 home
AU$1,169 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Living area
Property grounds
Beach
Private kitchen
Exceptional
(92 reviews)

Chesapeake Bay Cottage

Churchton

8% off
AU$3,470
for 7 nights, 1 cottage
AU$496 per night
includes taxes & fees
Chesapeake Bay Cottage
Thomas Harrison House looking from St. Michaels Town Harbor
View of Side of Harrison House and St. Michaels Harbor from Locust Street
Rear Porch for relaxing or for barbecues!
View of St. Michaels Harbor from Town Park in front of Thomas Harrison House
Exceptional
(142 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels

8% off
AU$7,475
for 7 nights, 1 home
AU$1,068 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Kitchen with peak into living room
Foyer into Living Room
Living Room into Kitchen/Dining
Kitchen/dining
Exceptional
(90 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
AU$6,086
for 7 nights, 1 home
AU$869 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Convenient open-concept design:  kitchen, dining and living areas
Exceptional
(161 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
AU$3,121
for 7 nights, 1 home
AU$446 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Room
Living area
Interior
Property grounds
Exceptional
(14 reviews)

Waterfront 4 BR home with private pier and boat dock

Grasonville

8% off
AU$7,685
for 7 nights, 1 home
AU$1,098 per night
includes taxes & fees
Waterfront 4 BR home with private pier and boat dock
Living area
Pool
Exterior
Interior
Exceptional
(230 reviews)

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis

8% off
AU$4,592
for 7 nights, 1 home
AU$656 per night
includes taxes & fees
Stunning Waterfront Cottage in the Sailing Capital of the World!
Exterior
Exterior
Living area
Interior
Exceptional
(5 reviews)

Waterfront Sanctuary only 50 Min. From DC/Balt.

Shady Side

12% off
AU$7,857
for 7 nights, 1 home
AU$1,122 per night
includes taxes & fees
Waterfront Sanctuary only 50 Min. From DC/Balt.
Private kitchen
Exterior
Living area
Exterior
Exceptional
(66 reviews)

Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay

Cambridge

8% off
AU$10,137
for 7 nights, 1 home
AU$1,448 per night
includes taxes & fees
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Exterior
New Kitchen 2022
Property grounds
Dining room
Exceptional
(64 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
AU$5,237
for 7 nights, 1 home
AU$748 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Dining Room - Seats 6
View down the lane
Living Room with flat screen TV and sleeper sofa
Custom kitchen
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,842
for 7 nights, 1 cottage
AU$406 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Property grounds
Private kitchen
Living area
Interior
Exceptional
(10 reviews)

3-bedroom waterfront retreat in Secretary, Maryland

Secretary

8% off
AU$4,828
for 7 nights, 1 home
AU$690 per night
includes taxes & fees
3-bedroom waterfront retreat in Secretary, Maryland
Interior
Dining
Private kitchen
Private kitchen
Exceptional
(10 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$4,087
for 7 nights, 1 cottage
AU$584 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Private kitchen
Pool
Interior
Property grounds
Exceptional
(215 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville

12% off
AU$4,612
for 7 nights, 1 room
AU$659 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Exterior detail
Be ready to float! Bring your own inner tubes  and tennis shoes!
Living area
Interior
Exceptional
(143 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
AU$2,910
for 7 nights, 1 cottage
AU$416 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Open-concept living area and kitchen
Beautiful North Beach, MD
Directly next door to Sunrise Garden park
Beautiful views from your own private balcony!
Exceptional
(20 reviews)

Unbelievable beach views for 6

North Beach

8% off
AU$2,770
for 7 nights, 1 apartment
AU$396 per night
includes taxes & fees
Unbelievable beach views for 6
Property grounds
Exterior
Living area
Private kitchen
Exceptional
(19 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman

8% off
AU$4,117
for 7 nights, 1 cottage
AU$588 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Interior
Living area
Private kitchen
Exterior
Exceptional
(407 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
AU$2,923
for 7 nights, 1 home
AU$418 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!
Living area
Outdoor dining
Property grounds
Private kitchen
Exceptional
(12 reviews)

High Water Guest House<br>

Cambridge

8% off
AU$3,799
for 7 nights, 1 home
AU$543 per night
includes taxes & fees
High Water Guest House<br>
Property grounds
Foyer
Bathroom
Exterior
Exceptional
(26 reviews)

Guest Quarters at the Inn - 102

North Beach

8% off
AU$2,085
for 7 nights, 1 apartment
AU$298 per night
includes taxes & fees
Guest Quarters at the Inn - 102
Light and bright dining room with space for 6 (plus a high chair).
Light and bright dining room with space for 6 (plus a high chair).
Light and bright dining room with space for 6 (plus a high chair).
Recently renovated kitchen with quartz countertops, stainless steel appliances, and all the gadgets, tools, and amenities you need to cook wonderful meals.
Exceptional
(7 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
AU$3,453
for 7 nights, 1 home
AU$493 per night
includes taxes & fees
Cozy Cottage with Beach Access
fridge with ice maker
Outdoor dining
Dining
Exterior detail
Exceptional
(30 reviews)

Eastern Shore Waterside Cottage Near St. Michaels

Neavitt

8% off
AU$3,364
for 7 nights, 1 cottage
AU$481 per night
includes taxes & fees
Eastern Shore Waterside Cottage Near St. Michaels
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Travel to arty Easton

Come and experience Easton and its festivals, art galleries and live music. Renowned for its museums, theatres and bird watching, this city welcomes all visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Easton

Are you hoping to discover attractions to see while you're in the area? Venture out of your holiday home and experience everything that makes Easton a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (7.9 mi / 12.7 km)
  • Queenstown Harbor Golf (15.7 mi / 25.2 km)
  • Talbot Massage (0.7 mi / 1.2 km)
  • Easton Cycle and Sport (0.8 mi / 1.3 km)
  • Hog Neck Golf Course (3.7 mi / 5.9 km)
  • Paul Reed Smith Guitars (19.6 mi / 31.5 km)

Exploring the natural features in Easton

Whether you're looking for fun outdoor activities or just want to take in the scenery, Easton is a great place to spend some time outside. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Gerry Boyle Park at Great Marsh (13.2 mi / 21.2 km)
  • Long Wharf Park (13.7 mi / 22 km)
  • Chesapeake Bay Environmental Center (14.5 mi / 23.4 km)
  • Northern Chesapeake Bay (19.6 mi / 31.5 km)
  • Bay Ridge Beach (23.7 mi / 38.1 km)
  • Sandy Point Beach (23.7 mi / 38.2 km)

Travelling to and around Easton

The nearest airport is in Easton, MD (ESN-Easton - Newnam), located 2.6 mi (4.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Georgetown, DE (GED-Sussex County), which is 38.9 mi (62.5 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Easton?
Bed & breakfasts are the most popular type of holiday home in Easton, according to our data. Even if you have something a little different in mind, Stayz has properties in all sizes and shapes. Explore our options to find your perfect fit.
How much does it cost to rent a holiday home in Easton?
The average price for a holiday home in Easton depends on several factors, such as property type, length of stay and season. Whether you're searching for a sprawling villa with a pool or a comfy cabin for you and your other half, just enter your travel dates to discover stays with terrific value.
How much does it cost to rent a beach house in Easton?
When you travel and the size and style of the property will influence the cost of your beachside escape. Type in your Easton travel dates to view your available options on Stayz. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to choose the features and amenities you want.
Are there pet-friendly holiday homes in Easton?
Pack a travel bag for the pup in your life because Easton has seven holiday homes that welcome pets with open arms. Let your furriest pal have fun with the family at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and dates, then check the "Pets allowed" filter box.
What are popular home amenities in Easton?
When it comes to home amenities that guests search for in Easton, a garden, a fireplace and a restaurant dining guide rank highest. With Stayz holiday homes, there are options to suit your taste and style, whether you're travelling with family members, friends or even pets.
Are there holiday homes in Easton that welcome kids?
Easton has seven family-friendly holiday homes to pick from. And tracking down a stay that welcomes kiddos is a breeze with Stayz's "Properties good for families" filter. On top of having the entire place to yourselves, you'll enjoy access to perks and amenities such as dining rooms, yards and private pools.
What are the top attractions for families in Easton?
Keep the kids happy at these fantastic family-friendly attractions in Easton:
  • Chesapeake Bay Maritime Museum
  • St. Michaels Museum
  • Historical Society of Talbot County
Are there one-bedroom holiday homes in Easton?
Take your pick from six one-bedroom homes in Easton. Whether you'd like a comfy cottage or a condo, our one-bedroom homes are perfect if you don't require lots of room. One of the perks of having your own place? You'll never have to share your holiday with strangers.
How old do you have to be to rent a holiday home in Easton?
The minimum age can vary across properties on Stayz, so check the rules of the holiday home in Easton you want. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Easton for?
It's up to the Easton property. To see all available options offering extended stays, simply type your dates and number of guests into the Stayz search page. You can enjoy having the property to yourself, as well as comforts such as a fully-equipped kitchen and outdoor spaces to play in. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

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