Easton holiday rentals

We found 611 holiday rentals — enter your dates for availability
Discover a selection of 33 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:18 Dec - 25 Dec

Kitchen
Kitchen
Exterior
Kitchen
Exceptional
(31 reviews)

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

Stevensville

12% off
AU$2,958
for 7 nights, 1 room
AU$423 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Interior
Interior
Room
Dining
Exceptional
(107 reviews)

Cass-Away Luxury Houseboat

Grasonville

7% off
AU$1,873
for 7 nights, 1 houseboat
AU$268 per night
includes taxes & fees
Cass-Away Luxury Houseboat
Room
Private kitchen
Dining
Interior
Exceptional
(21 reviews)

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

Annapolis

16% off
AU$7,803
for 7 nights, 1 home
AU$1,115 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
View from Foyer into Great Room
Pool
View from Pier back to house!
Dining table- seats 10!
Exceptional
(145 reviews)

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

Easton

8% off
AU$11,236
for 7 nights, 1 home
AU$1,605 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Another view from above.
The view off of the point, breathtaking.
Interior
Interior
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
AU$6,816
for 7 nights, 1 home
AU$974 per night
includes taxes & fees
Grandview- Main House
Living area
Interior
Dining
Interior
Excellent
(6 reviews)

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Royal Oak

8% off
AU$12,676
for 7 nights, 1 cottage
AU$1,811 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Delightful front garden welcomes you when approaching house from driveway
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Exceptional
(163 reviews)

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

Sherwood

10% off
AU$3,415
for 7 nights, 1 home
AU$488 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Living area
Exterior
Property grounds
Private kitchen
Exceptional
(25 reviews)

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

Tilghman

8% off
AU$4,184
for 7 nights, 1 cottage
AU$598 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Private kitchen
Dining
Interior
Private kitchen
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$5,023
for 7 nights, 1 cottage
AU$718 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Exterior
Living area
Interior
Private kitchen
Exceptional
(51 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
AU$9,094
for 7 nights, 1 home
AU$1,299 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Property grounds
New Kitchen 2022
Dining room
Exterior
Exceptional
(65 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
AU$5,168
for 7 nights, 1 home
AU$738 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Interior
Private kitchen
Interior
Dining
Exceptional
(7 reviews)

Arcadia Shores on the Cove.

Easton

8% off
AU$6,925
for 7 nights, 1 home
AU$989 per night
includes taxes & fees
Arcadia Shores on the Cove.
Dining Room - Seats 6
View down the lane
Sit and stay a while!
Custom kitchen
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,863
for 7 nights, 1 cottage
AU$409 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Room
Private kitchen
Interior
Property grounds
Exceptional
(10 reviews)

3-bedroom waterfront retreat in Secretary, Maryland

Secretary

8% off
AU$4,844
for 7 nights, 1 home
AU$692 per night
includes taxes & fees
3-bedroom waterfront retreat in Secretary, Maryland
Dining
Living area
Exterior
Private kitchen
Exceptional
(7 reviews)

Waterfront- 5-bedroom house with dock in charming North Beach

North Beach

8% off
AU$11,010
for 7 nights, 1 home
AU$1,573 per night
includes taxes & fees
Waterfront- 5-bedroom house with dock in charming North Beach
Beautiful North Bach, MD
Beautiful North Beach, MD
Directly next door to Sunrise Garden park
Beautiful views from your own private balcony!
Exceptional
(21 reviews)

Unbelievable beach views for 6

North Beach

8% off
AU$3,592
for 7 nights, 1 apartment
AU$513 per night
includes taxes & fees
Unbelievable beach views for 6
Eating Area adjacent Kitchen
Front of W Melson House
Large Screened Porch with rocking chairs
New and fully equipped Kitchen
Exceptional
(209 reviews)

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

St. Michaels

8% off
AU$4,492
for 7 nights, 1 cottage
AU$642 per night
includes taxes & fees
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Room
Living area
Interior
Living area
Exceptional
(7 reviews)

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

St. Michaels

17% off
AU$3,682
for 7 nights, 1 home
AU$526 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
Living area
Be ready to float! Bring your own inner tubes and tennis shoes!
Exterior detail
Interior
Exceptional
(144 reviews)

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

Bozman

12% off
AU$2,959
for 7 nights, 1 cottage
AU$423 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Exterior
Pool
Living area
Marina
Exceptional
(233 reviews)

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis

8% off
AU$4,622
for 7 nights, 1 home
AU$660 per night
includes taxes & fees
Stunning Waterfront Cottage in the Sailing Capital of the World!
Kitchen with peak into living room
Foyer into Living Room
Foyer with stairs to second floor peak into 1st floor master bedroom
Kitchen/dining
Exceptional
(92 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
AU$6,077
for 7 nights, 1 home
AU$868 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Private kitchen
Living area
Interior
Property grounds
Exceptional
(414 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
AU$2,931
for 7 nights, 1 home
AU$419 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!
Dining
Marina
Private kitchen
Marina
Exceptional
(7 reviews)

New, Intown Waterfront Townhome wPool & Location!

Cambridge

10% off
AU$4,299
for 7 nights, 1 home
AU$614 per night
includes taxes & fees
New, Intown Waterfront Townhome wPool & Location!
Park half block from house
St. Michaels Harbor from Park down street
Eating area in panelled Family Room. Eat here, in dining room, or on porch!
Large screened porch with ceiling fan allows outdoor dining and relaxing.
Exceptional
(150 reviews)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St. Michaels

8% off
AU$4,146
for 7 nights, 1 cottage
AU$592 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

  • 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)
  • Paul Reed Smith Guitars (19.6 mi / 31.5 km)
  • Talbot Massage (0.7 mi / 1.2 km)
  • Hog Neck Golf Course (3.7 mi / 5.9 km)
  • Triple Creek Winery (6.4 mi / 10.3 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)
  • Eastern Neck National Wildlife Refuge (19.4 mi / 31.2 km)
  • Northern Chesapeake Bay (19.6 mi / 31.5 km)
  • Sandy Point Beach (23.7 mi / 38.2 km)
  • Blackwater National Wildlife Refuge (24.5 mi / 39.4 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 best area to stay in Easton when booking a holiday rental?
When considering a holiday rental in Easton, Maryland, the best area to stay is the charming downtown district. This vibrant neighbourhood is known for its picturesque streets and a friendly setting, making it a delightful spot for visitors. Here, you'll find an array of properties, ranging from quaint cottages to elegant historical homes, providing ample choices for those seeking a comfortable stay.Downtown Easton is not only convenient for accommodation but also offers a wealth of attractions. One of the highlights is the Academy Art Museum, which features a diverse collection of art and hosts various exhibitions and events throughout the year. Additionally, the nearby Talbot County Courthouse is an architectural gem worth exploring, showcasing the town's rich history.Another appealing aspect of this area is its proximity to lovely parks and waterfront activities along the Tred Avon River. Visitors can enjoy scenic strolls, kayaking, or simply relaxing by the water.
Where are the best areas for renting a beach house in Easton?
For renting a beach house in Easton, one should consider the nearby areas along the Chesapeake Bay, particularly the towns of Oxford and St. Michaels. Oxford, just a short drive from Easton, offers a lovely selection of waterfront properties with direct access to the bay. Many of these homes come with private docks, allowing for boating and fishing right from your doorstep. Amenities often include spacious decks for outdoor dining, fire pits for evening gatherings, and fully equipped kitchens to cater to family meals.St. Michaels, known for its charming historic district and vibrant waterfront, also presents excellent rental opportunities. Here, you can find beautifully restored homes that feature traditional architecture while providing modern comforts such as air conditioning, Wi-Fi, and sometimes even pools. The area is rich in dining options and boutique shops, enhancing the overall experience for visitors.In addition, both towns provide easy access to outdoor activities, including kayaking, paddleboarding, and cycling along scenic trails. Properties in these regions often feature beautiful views of the water, lush gardens, and spacious living areas, making them ideal for families or groups seeking a relaxing beach getaway.
What is the most popular type of holiday rental accomodation in Easton?
In Easton, holiday houses are the most popular type of holiday rental, with around 128 available throughout the area. These houses typically offer spacious rooms, superb for families or groups, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios for relaxation. While there are several apartments as well, the holiday houses dominate the rental market, providing a cozy feel in a charming setting.
Are there any family house rentals in Easton?
In Easton, Maryland, there are numerous family-friendly house rentals available, with around 26 options to choose from. This charming town, known for its picturesque streets and vibrant arts scene, offers a variety of homes that cater to families. Many of these properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.Visitors can expect amenities such as Wi-Fi, air conditioning, and sometimes even game rooms for entertainment. The locale is conveniently situated near attractions like the Easton Historic District, which boasts quaint shops and restaurants, as well as the beautiful parks and waterfront along the Tred Avon River, great for picnics and outdoor activities.
Can I rent a holiday home with a pool or hot tub in Easton?
In Easton, Maryland, there are plenty of holiday homes available for rent that come with pools and hot tubs, with around 20 options to choose from. This charming town offers a blend of historic charm and modern amenities, making it an ideal destination for relaxation. Many of these properties feature private pools where families can enjoy sunny days, as well as hot tubs for unwinding in the evenings.Travellers can expect amenities such as spacious living areas, well-equipped kitchens for preparing meals, and outdoor spaces superb for entertaining or enjoying a quiet moment. Some rentals may also include additional features like fire pits, patios, and gardens, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Easton?
In Easton, Maryland, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. The town features a variety of charming properties, many of which come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living spaces, ideal for families or groups.You may find houses that offer outdoor areas great for pets to roam and play, as well as proximity to local parks and green spaces. Easton is known for its quaint downtown area, where visitors can enjoy boutique shopping and dining, some of which are pet-friendly. The nearby Oxford area also offers lovely waterfront views and walking trails that are great for leisurely strolls with your furry companions.
Are there any remote work holiday rentals in Easton?
In Easton, Maryland, there are numerous remote work-friendly holiday rentals available, with around 128 options to choose from. This charming town, known for its historic architecture and vibrant arts scene, offers a variety of properties that cater to remote workers. Many rentals provide essential amenities such as free Wi-Fi, dedicated workspace areas, and comfortable living conditions, making it easy to stay productive while enjoying a change of scenery.The area surrounding Easton boasts picturesque views and a relaxed atmosphere, superb for unwinding after a day of work. Visitors can explore local attractions like the Academy Art Museum or take leisurely strolls along the Tred Avon River. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Easton?
In Easton, popular holiday rentals typically come equipped with essential amenities that cater to a comfortable stay. Most properties feature a fully equipped kitchen, allowing guests to prepare their own meals. Onsite parking is also a common convenience, making it easy for visitors to explore the charming town. Additionally, many rentals include a coffee and tea maker for that morning brew, along with a deck or patio that provides outdoor space for relaxation. A fireplace is another desirable feature, offering warmth and a cosy atmosphere during cooler evenings.
When is the best time to visit Easton for a holiday rental?
The best time to visit Easton for a holiday rental is during the summer months, particularly in July, when the area comes alive with vibrant activities and warm weather. This peak season, spanning from June to August, is great for those looking to enjoy outdoor adventures, explore local festivals, and take in the charming waterfront views along the Tred Avon River.In July, temperatures typically range from the low 20s to mid-30s Celsius, creating an ideal climate for leisurely strolls through Easton's historic district or enjoying al fresco dining at one of the many delightful restaurants. The bustling atmosphere brings together both locals and tourists, offering a wonderful opportunity to engage with the community and fully immerse yourself in the local culture.For those seeking a more budget-friendly option, December offers a unique charm with festive decorations and a quieter ambiance. While it's outside of the main tourist season, visitors can still enjoy the warmth of local holiday events and explore the quaint shops at a leisurely pace.Ultimately, the best time to book a holiday rental in Easton hinges on whether you prefer the lively summer scene or the tranquil beauty of winter festivities.
What are the top attractions in Easton?
In Easton, Maryland, visitors can take part in a variety of attractions that showcase the area's rich history and vibrant culture. The historic downtown area is a charming spot, featuring beautifully preserved 18th and 19th-century buildings, boutique shops, and local eateries. Notable sites include the Talbot County Courthouse and the nearby Academy Art Museum, which offers a range of exhibitions and educational programmes.For those interested in outdoor activities, the surrounding landscapes provide opportunities for hiking and water sports. The nearby Tred Avon River is popular for kayaking and boating, while the scenic landscapes of Oxford, just a short drive away, are ideal for leisurely strolls or picnics by the waterfront.Easton's arts scene is also noteworthy, with events such as the annual Waterfowl Festival drawing visitors from all over. Additionally, the area hosts various festivals and markets throughout the year, making it a lively destination for tourists.
Are all fees included in the Easton holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Easton holiday homes with parking?
Stayz offers a wide selection of holiday homes in Easton with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Easton holiday homes?
You can find great discounts on holiday homes in Easton on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Easton holiday home booking on Stayz?
To find Easton holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Easton?
A long-stay holiday home in Easton is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Easton holiday home?
Book your Easton holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Easton?
Prices for holiday homes in Easton vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Easton to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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